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Showing 108 of 135 sailings

Explora Journeys · EXPLORA IIIRound-trip

Caribbean 14 nights Oct 25, 2026 from Miami, Florida

Miami, Florida · Saint John/cruz Bay · … · Miami, Florida11 ports

Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Road Bay, Anguilla · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay Beach Private Catamaran Sail & Snorkel Random Wind 'Paradise Day Sail' +5 more

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from $12,280

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Windstar · Star PrideRound-trip

Caribbean 11 nights Oct 28 – Nov 8, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico11 ports

San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Falmouth Harbour, Antigua · Les Saintes, Guadeloupe · Rodney Bay, St. Lucia · St. Georges, Grenada, West Indies · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +6 more

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from $3,930

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Explora Journeys · EXPLORA IIIOne-way

Caribbean 14 nights Nov 1, 2026 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · Miami, Florida6 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Road Bay, Anguilla · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Mt. Liamuiga Volcano Crater Hike Private Open-Top Mini Moke Island Tour of St. Barts +2 more

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from $5,680

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Silversea · Silver ShadowRound-trip

Caribbean 11 nights Nov 7 – Nov 18, 2026 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +3 more

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from $7,150

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Explora Journeys · EXPLORA IIIRound-trip

Caribbean 7 nights Nov 8, 2026 from Miami, Florida

Miami, Florida · Providenciales, Turks & Caicos · … · Miami, Florida13 ports

Miami, Florida · Providenciales, Turks & Caicos · Puerto Plata, Dominican Republic · La Romana, Dominican Republic · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Frederikstad, St. Croix · Ain Sokhna, Egypt · Puerto Plata, Dominican Republic · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & Reef The full 27 jumps at the Damajagua Waterfalls Saona Island Private Speedboat & Natural Pool Day +6 more

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from $8,735

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Windstar · Star PrideRound-trip

Caribbean 7 nights Nov 15 – Nov 22, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Cruz Bay, St. John · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike Private Open-Top Mini Moke Island Tour of St. Barts +3 more

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from $6,153

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Silversea · Silver ShadowRound-trip

Caribbean 12 nights Nov 18 – Nov 30, 2026 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida9 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +4 more

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from $8,550

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Azamara · Azamara JourneyRound-trip

Caribbean 14 nights Nov 21 – Dec 5, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · San Juan, Puerto Rico15 ports

San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls The Baths National Park Private Half-Day Island Adventure & Trunk Bay Beach Schotia Private Game Reserve +9 more

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from $5,769

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Oceania · Oceania VistaRound-trip

Caribbean 12 nights Nov 25 – Dec 7, 2026 from Miami, Florida

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · St. John's, Antigua · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Random Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +4 more

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from $4,025

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Azamara · Azamara JourneyRound-trip

Caribbean 14 nights Nov 28 – Dec 12, 2026 from Bridgetown, Barbados

Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados15 ports

Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol Tours Boiling Lake Hike Mt. Liamuiga Volcano Crater Hike +9 more

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from $5,719

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Explora Journeys · EXPLORA IIIOne-way

Caribbean 14 nights Nov 29, 2026 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · Miami, Florida6 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Grand Turk, Turks and Caicos · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Mt. Liamuiga Volcano Crater Hike Private Open-Top Mini Moke Island Tour of St. Barts +2 more

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from $5,585

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Regent · Seven Seas GrandeurRound-trip

Bahamas 10 nights Nov 29 – Dec 9, 2026 from Miami, Florida

Miami, Florida · Willis Island · … · Miami, Florida10 ports

Miami, Florida · Willis Island · San Juan, Puerto Rico · Gustavia, St. Barts · Philipsburg, St. Maarten · Frederikstad, St. Croix · La Romana, Dominican Republic · Willis Island · Nassau, Bahamas · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis Island Walk El Morro & Old San Juan's City Walls Private Open-Top Mini Moke Island Tour of St. Barts +3 more

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from $6,949

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Windstar · Star PrideRound-trip

Caribbean 7 nights Nov 29 – Dec 6, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +3 more

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from $3,913

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Silversea · Silver ShadowRound-trip

Caribbean 10 nights Nov 30 – Dec 10, 2026 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +2 more

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from $6,450

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Oceania · Oceania AlluraRound-trip

Caribbean 10 nights Dec 2 – Dec 12, 2026 from Miami, Florida

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten · Frederikstad, St. Croix · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Private Open-Top Mini Moke Island Tour of St. Barts Random Wind 'Paradise Day Sail' +1 more

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from $4,095

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Silversea · Silver SpiritRound-trip

Caribbean 7 nights Dec 5 – Dec 12, 2026 from Bridgetown, Barbados

Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports

Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Deshaies, Guadeloupe · Gustavia, St. Barts · Codrington, Barbuda · Castries, St. Lucia · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private Sail Mount Pelée & Saint-Pierre Jardin Botanique de Deshaies at Opening Hour +3 more

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from $4,550

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Explora Journeys · EXPLORA IIIOne-way

Caribbean 14 nights Dec 6, 2026 from Miami, Florida to San Juan, Puerto Rico

Miami, Florida · Saint John/cruz Bay · … · San Juan, Puerto Rico6 ports

Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Gustavia, St. Barts · San Juan, Puerto Rico

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay Beach Private Catamaran Sail & Snorkel Private Open-Top Mini Moke Island Tour of St. Barts +1 more

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from $4,200

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Oceania · Oceania MarinaRound-trip

Caribbean 12 nights Dec 10 – Dec 22, 2026 from Miami, Florida

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Gustavia, St. Barts · St. John's, Antigua · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Private Open-Top Mini Moke Island Tour of St. Barts Private Half-Day Island Adventure & Trunk Bay Beach +4 more

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from $2,640

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Regent · Seven Seas SplendorRound-trip

Caribbean 17 nights Dec 11 – Dec 28, 2026 from Galveston, Texas

Galveston, Texas · Willis Island · … · Galveston, Texas15 ports

Galveston, Texas · Willis Island · Montego Bay, Jamaica · Ocho Rios, Jamaica · Willis Island · Punta Cana, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · Gustavia, St. Barts · St. John's, Antigua · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Galveston, Texas

★ Bucket-list Moody Gardens Zodiac Circumnavigation of Willis Island Martha Brae River Bamboo Rafting Blue Hole +7 more

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from $12,699

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Silversea · Silver RayRound-trip

Caribbean 11 nights Dec 11 – Dec 22, 2026 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Deshaies, Guadeloupe · Road Town, Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike +3 more

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from $5,450

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Azamara · Azamara JourneyRound-trip

Caribbean 16 nights Dec 12 – Dec 28, 2026 from Bridgetown, Barbados

Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados16 ports

Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Gustavia, St. Barts · Saint- Pierre · Port Elizabeth, Saint Vincent · Scarborough, Tobago · Mayreau, Grenadines · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol Tours Boiling Lake Hike Mt. Liamuiga Volcano Crater Hike +10 more

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from $7,459

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Oceania · Oceania AlluraRound-trip

Caribbean 9 nights Dec 12 – Dec 21, 2026 from Miami, Florida

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida6 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Random Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +1 more

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from $3,290

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Windstar · Star PrideRound-trip

Caribbean 7 nights Dec 13 – Dec 20, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +3 more

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from $3,983

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Azamara · Azamara JourneyOne-way

Caribbean 10 nights Dec 18 – Dec 28, 2026 from San Juan, Puerto Rico to Bridgetown, Barbados

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Bridgetown, Barbados10 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Gustavia, St. Barts · Saint- Pierre · Port Elizabeth, Saint Vincent · Scarborough, Tobago · Mayreau, Grenadines · Bridgetown, Barbados

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter The Baths National Park Private Half-Day Island Adventure & Trunk Bay Beach +5 more

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from $2,509

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Explora Journeys · EXPLORA IRound-trip

Caribbean 15 nights Dec 20, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · San Juan, Puerto Rico13 ports

San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Gustavia, St. Barts · Road Bay, Anguilla · Miami, Florida · Puerto Plata, Dominican Republic · Ain Sokhna, Egypt · Saint John/cruz Bay · Jost Van Dyke, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike Norman Island Private Open-Top Mini Moke Island Tour of St. Barts +6 more

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from $12,365

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Windstar · Wind SurfRound-trip

Asia 7 nights Dec 26 – Jan 2, 2027 from Philipsburg, St. Maarten

Philipsburg, St. Maarten · Gustavia, St. Barts · … · Philipsburg, St. Maarten8 ports

Philipsburg, St. Maarten · Gustavia, St. Barts · Jeju Island South Korea · Roseau, Dominica · Mayreau, Grenadines · Les Saintes, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten

★ Bucket-list Random Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts Seongsan Ilchulbong Boiling Lake Hike +3 more

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from $3,377

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Windstar · Star PrideRound-trip

Caribbean 7 nights Dec 27 – Jan 3, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +3 more

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from $3,563

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Oceania · Oceania AlluraRound-trip

Caribbean 10 nights Dec 28 – Jan 7, 2027 from Miami, Florida

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Random Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +2 more

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from $6,499

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Windstar · Wind SurfRound-trip

Caribbean 7 nights Jan 2 – Jan 9, 2027 from Philipsburg, St. Maarten

Philipsburg, St. Maarten · Falmouth Harbour, Antigua · … · Philipsburg, St. Maarten8 ports

Philipsburg, St. Maarten · Falmouth Harbour, Antigua · Road Bay, Anguilla · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten

★ Bucket-list Random Wind 'Paradise Day Sail'Antigua Stingray City Private Island Hopping The Baths of Virgin Gorda +3 more

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from $2,798

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Silversea · Silver ShadowRound-trip

Caribbean 7 nights Jan 3 – Jan 10, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts Barbuda's Pink Sand Beach at Dawn, Private & Empty +3 more

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from $6,150

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Azamara · Azamara JourneyOne-way

Caribbean 9 nights Jan 5 – Jan 14, 2027 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Miami, Florida8 ports

San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls The Baths National Park Private Open-Top Mini Moke Island Tour of St. Barts Random Wind 'Paradise Day Sail' +4 more

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from $2,349

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Explora Journeys · EXPLORA IIIOne-way

Caribbean 16 nights Jan 5, 2027 from Miami, Florida to San Juan, Puerto Rico

Miami, Florida · Saint John/cruz Bay · … · San Juan, Puerto Rico7 ports

Miami, Florida · Saint John/cruz Bay · Gustavia, St. Barts · St. John's, Antigua · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Open-Top Mini Moke Island Tour of St. Barts Private Half-Day Island Adventure & Trunk Bay Beach Norman Island +2 more

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from $5,920

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Silversea · Silver NovaOne-way

Caribbean 12 nights Jan 6 – Jan 18, 2027 from Miami, Florida to Bridgetown, Barbados

Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados9 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +5 more

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from $5,850

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Windstar · Wind SurfRound-trip

Asia 7 nights Jan 9 – Jan 16, 2027 from Philipsburg, St. Maarten

Philipsburg, St. Maarten · Jeju Island South Korea · … · Philipsburg, St. Maarten8 ports

Philipsburg, St. Maarten · Jeju Island South Korea · Les Saintes, Guadeloupe · Mayreau, Grenadines · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten

★ Bucket-list Random Wind 'Paradise Day Sail'Seongsan Ilchulbong Sail Into the Bay of Les Saintes at Dawn Salt Whistle Bay +3 more

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from $3,727

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Silversea · Silver ShadowOne-way

Caribbean 10 nights Jan 10 – Jan 20, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · Bridgetown, Barbados11 ports

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Iles des Saintes, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Catamaran Charter Private Open-Top Mini Moke Island Tour of St. Barts Barbuda's Pink Sand Beach at Dawn, Private & Empty +7 more

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from $4,650

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Windstar · Star PrideRound-trip

Caribbean 7 nights Jan 10 – Jan 17, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Cruz Bay, St. John · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike Private Open-Top Mini Moke Island Tour of St. Barts +3 more

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from $4,928

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Silversea · Silver RayRound-trip

Caribbean 11 nights Jan 16 – Jan 27, 2027 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Road Town, Tortola, B.V.I. · Anguilla, Caribbean · Port of Charlestown, Nevis, St. Kitts and Nevis · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +3 more

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from $6,650

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Windstar · Wind SurfRound-trip

Caribbean 7 nights Jan 16 – Jan 23, 2027 from Philipsburg, St. Maarten

Philipsburg, St. Maarten · Road Bay, Anguilla · … · Philipsburg, St. Maarten9 ports

Philipsburg, St. Maarten · Road Bay, Anguilla · Jost Van Dyke, British Virgin Islands · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Falmouth Harbour, Antigua · Philipsburg, St. Maarten

★ Bucket-list Random Wind 'Paradise Day Sail'Private Island Hopping Private Catamaran Charter The Baths of Virgin Gorda +3 more

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from $3,638

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Silversea · Silver ShadowOne-way

Caribbean 10 nights Jan 20 – Jan 30, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico

Bridgetown, Barbados · Bequia, Grenadines · … · San Juan, Puerto Rico11 ports

Bridgetown, Barbados · Bequia, Grenadines · Castries, St. Lucia · Trois Ilets · Roseau, Dominica · Iles des Saintes, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private Sail Cosol Tours La Savane des Esclaves +7 more

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from $7,150

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Silversea · Silver RayRound-trip

Caribbean 11 nights Jan 27 – Feb 7, 2027 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Deshaies, Guadeloupe · Anguilla, Caribbean · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +3 more

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from $9,250

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Explora Journeys · EXPLORA IOne-way

Caribbean 7 nights Jan 29, 2027 from Miami, Florida to Manaus, Brazil

Miami, Florida · Puerto Plata, Dominican Republic · … · Manaus, Brazil14 ports

Miami, Florida · Puerto Plata, Dominican Republic · Philipsburg, St. Maarten · Terre-de-haut, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · Gustavia, St. Barts · Saint-Pierre, France · Bridgetown, Barbados · Port of Spain, Trinidad · Macapa, Brazil · Santarem, Brazil · Boca da Valeria, Brazil · Manaus, Brazil

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua Waterfalls Random Wind 'Paradise Day Sail'Private Catamaran Sail & Snorkel +9 more

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from $11,625

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Explora Journeys · EXPLORA IIIRound-trip

Caribbean 14 nights Jan 29, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico11 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · St. John's, Antigua · Providenciales, Turks & Caicos · Key West, Florida · Miami, Florida · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Saint John/cruz Bay · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Private Half-Day Island Adventure & Trunk Bay Beach Iguana Island & Reef +5 more

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from $10,800

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Silversea · Silver ShadowRound-trip

Caribbean 7 nights Jan 30 – Feb 6, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Little Bay, Montserrat, Leeward Islands · Codrington, Barbuda · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Soufrière Hills Volcano Exclusion Zone Helicopter…Barbuda's Pink Sand Beach at Dawn, Private & Empty +3 more

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from $6,150

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Explora Journeys · EXPLORA IOne-way

Caribbean 12 nights Feb 5, 2027 from San Juan, Puerto Rico to Manaus, Brazil

San Juan, Puerto Rico · Gustavia, St. Barts · … · Manaus, Brazil9 ports

San Juan, Puerto Rico · Gustavia, St. Barts · Saint-Pierre, France · Bridgetown, Barbados · Port of Spain, Trinidad · Macapa, Brazil · Santarem, Brazil · Boca da Valeria, Brazil · Manaus, Brazil

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Open-Top Mini Moke Island Tour of St. Barts Île aux Marins Swim with wild green sea turtles + two shipwrecks… +4 more

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from $8,190

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Explora Journeys · EXPLORA IIIRound-trip

Caribbean 14 nights Feb 5, 2027 from Miami, Florida

Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida11 ports

Miami, Florida · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Saint John/cruz Bay · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Terre-de-haut, Guadeloupe · Puerto Plata, Dominican Republic · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +5 more

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from $10,840

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Oceania · Oceania AlluraOne-way

Caribbean 7 nights Feb 5 – Feb 12, 2027 from Miami, Florida to San Juan, Puerto Rico

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico6 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Gustavia, St. Barts · San Juan, Puerto Rico

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Random Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more

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from $3,320

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Silversea · Silver ShadowOne-way

Caribbean 10 nights Feb 6 – Feb 16, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · Bridgetown, Barbados11 ports

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Iles des Saintes, Guadeloupe · Roseau, Dominica · Trois Ilets · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Catamaran Charter Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +7 more

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from $5,750

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Silversea · Silver RayOne-way

Caribbean 12 nights Feb 7 – Feb 19, 2027 from Miami, Florida to Bridgetown, Barbados

Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados11 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Codrington, Barbuda · Deshaies, Guadeloupe · Roseau, Dominica · Fort-de-France, Martinique · Bequia, Grenadines · Bridgetown, Barbados

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike +7 more

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from $9,200

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Silversea · Silver ShadowOne-way

Caribbean 10 nights Feb 16 – Feb 26, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico

Bridgetown, Barbados · Bequia, Grenadines · … · San Juan, Puerto Rico11 ports

Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Castries, St. Lucia · Trois Ilets · Roseau, Dominica · Iles des Saintes, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private Sail Grenada Private Taxi Tour Cosol Tours +7 more

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from $7,450

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Explora Journeys · EXPLORA IOne-way

Caribbean 19 nights Feb 17, 2027 from Manaus, Brazil to Miami, Florida

Manaus, Brazil · Parintins, Brazil · … · Miami, Florida16 ports

Manaus, Brazil · Parintins, Brazil · Alter Do Chão · Macapa, Brazil · Devils Island, French Guiana · Bequia, Grenadines · Bridgetown, Barbados · Castries, St. Lucia · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · St. John's, Antigua · Road Bay, Anguilla · Virgin Gorda, British Virgin Islands · Grand Turk, Turks and Caicos · Miami, Florida

★ Bucket-list Meeting of the Waters Îles du Salut Tobago Cays & Mystique Full-Day Private Sail Swim with wild green sea turtles + two shipwrecks… +9 more

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from $11,865

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Oceania · Oceania AlluraOne-way

Caribbean 8 nights Feb 19 – Feb 27, 2027 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Gustavia, St. Barts · … · Miami, Florida7 ports

San Juan, Puerto Rico · Gustavia, St. Barts · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Open-Top Mini Moke Island Tour of St. Barts Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +3 more

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from $3,499

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Silversea · Silver RayOne-way

Caribbean 12 nights Feb 26 – Mar 10, 2027 from Bridgetown, Barbados to Miami, Florida

Bridgetown, Barbados · Bequia, Grenadines · … · Miami, Florida11 ports

Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Deshaies, Guadeloupe · Soufriere, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · Anguilla, Caribbean · Miami, Florida

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private Sail Grenada Private Taxi Tour Mount Pelée & Saint-Pierre +6 more

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from $8,900

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Silversea · Silver ShadowRound-trip

Caribbean 7 nights Feb 26 – Mar 5, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +3 more

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from $5,450

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Windstar · Wind SurfRound-trip

Caribbean 7 nights Feb 27 – Mar 6, 2027 from Philipsburg, St. Maarten

Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Philipsburg, St. Maarten8 ports

Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Road Bay, Anguilla · Falmouth Harbour, Antigua · Philipsburg, St. Maarten

★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin Gorda Private Catamaran Charter The Baths National Park +3 more

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from $3,008

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Silversea · Silver SpiritRound-trip

Caribbean 7 nights Feb 28 – Mar 7, 2027 from Bridgetown, Barbados

Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados8 ports

Bridgetown, Barbados · Castries, St. Lucia · Gustavia, St. Barts · Cruz Bay, St. John, U.S. Virgin Islands · Codrington, Barbuda · Roseau, Dominica · Bequia, Grenadines · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol Tours Private Open-Top Mini Moke Island Tour of St. Barts Trunk Bay Underwater Snorkel Trail & VI National P… +3 more

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from $5,150

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Windstar · Wind SurfRound-trip

Asia 7 nights Mar 6 – Mar 13, 2027 from Philipsburg, St. Maarten

Philipsburg, St. Maarten · Jeju Island South Korea · … · Philipsburg, St. Maarten8 ports

Philipsburg, St. Maarten · Jeju Island South Korea · Roseau, Dominica · Mayreau, Grenadines · Les Saintes, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten

★ Bucket-list Random Wind 'Paradise Day Sail'Seongsan Ilchulbong Boiling Lake Hike Salt Whistle Bay +3 more

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from $2,432

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Explora Journeys · EXPLORA IIIOne-way

Caribbean 7 nights Mar 7, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados

San Juan, Puerto Rico · Philipsburg, St. Maarten · … · Bridgetown, Barbados11 ports

San Juan, Puerto Rico · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Grand Turk, Turks and Caicos · Miami, Florida · Providenciales, Turks & Caicos · St. John's, Antigua · Pointe-a-Pitre, Guadeloupe · Bequia, Grenadines · Bridgetown, Barbados

★ Bucket-list Walk El Morro & Old San Juan's City Walls Random Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +7 more

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from $8,680

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Oceania · Oceania AlluraRound-trip

Caribbean 10 nights Mar 11 – Mar 21, 2027 from Miami, Florida

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Random Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +2 more

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from $4,849

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Windstar · Wind SurfRound-trip

Caribbean 6 nights Mar 13 – Mar 19, 2027 from Philipsburg, St. Maarten

Philipsburg, St. Maarten · Falmouth Harbour, Antigua · … · Philipsburg, St. Maarten9 ports

Philipsburg, St. Maarten · Falmouth Harbour, Antigua · Road Bay, Anguilla · Jost Van Dyke, British Virgin Islands · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten

★ Bucket-list Random Wind 'Paradise Day Sail'Antigua Stingray City Private Island Hopping Private Catamaran Charter +3 more

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from $2,868

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Explora Journeys · EXPLORA IIIRound-trip

Caribbean 15 nights Mar 14, 2027 from Miami, Florida

Miami, Florida · Providenciales, Turks & Caicos · … · Miami, Florida12 ports

Miami, Florida · Providenciales, Turks & Caicos · St. John's, Antigua · Pointe-a-Pitre, Guadeloupe · Bequia, Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Castries, St. Lucia · Martinique/fort De France · Gustavia, St. Barts · Virgin Gorda, British Virgin Islands · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & Reef Private Half-Day Island Adventure & Trunk Bay Beach Death in Paradise Filming Locations & Botanical Ga… +6 more

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from $10,185

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Silversea · Silver SpiritOne-way

Caribbean 12 nights Mar 19 – Mar 31, 2027 from Miami, Florida to Bridgetown, Barbados

Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados9 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Bequia, Grenadines · Bridgetown, Barbados

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +5 more

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from $6,800

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Explora Journeys · EXPLORA IIIOne-way

Caribbean 15 nights Mar 21, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico

Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico12 ports

Bridgetown, Barbados · St. Georges, Grenada, West Indies · Castries, St. Lucia · Martinique/fort De France · Gustavia, St. Barts · Virgin Gorda, British Virgin Islands · Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi Tour Cosol Tours Private Open-Top Mini Moke Island Tour of St. Barts +6 more

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from $10,710

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Oceania · Oceania AlluraRound-trip

Caribbean 10 nights Mar 21 – Mar 31, 2027 from Miami, Florida

Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Miami, Florida7 ports

Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Mt. Liamuiga Volcano Crater Hike Random Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +2 more

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from $5,199

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Regent · Seven Seas MarinerRound-trip

Caribbean 15 nights Mar 26 – Apr 10, 2027 from Miami, Florida

Miami, Florida · Willis Island · … · Miami, Florida15 ports

Miami, Florida · Willis Island · Tortola, B.V.I. · Gustavia, St. Barts · Fort-de-France, Martinique · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Puerto Plata, Dominican Republic · Willis Island · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis Island Jost Van Dyke Private Open-Top Mini Moke Island Tour of St. Barts +7 more

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from $11,099

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Explora Journeys · EXPLORA IIIRound-trip

Caribbean 7 nights Mar 29, 2027 from Miami, Florida

Miami, Florida · Saint John/cruz Bay · … · Miami, Florida11 ports

Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Gustavia, St. Barts · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Key West, Florida · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay Beach Private Catamaran Sail & Snorkel Norman Island +5 more

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from $9,450

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Regent · Seven Seas PrestigeOne-way

Bahamas 10 nights Mar 30 – Apr 9, 2027 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Tortola, B.V.I. · … · Miami, Florida11 ports

San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · La Romana, Dominican Republic · Willis Island · Nassau, Bahamas · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Jost Van Dyke Mt. Liamuiga Volcano Crater Hike Private Half-Day Island Adventure & Trunk Bay Beach +7 more

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from $6,399

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Regent · Seven Seas GrandeurOne-way

Mediterranean 14 nights Mar 31 – Apr 14, 2027 from Panama City, Panama to Miami, Florida

Panama City, Panama · Kiel Canal, Germany · … · Miami, Florida14 ports

Panama City, Panama · Kiel Canal, Germany · Cartagena, Spain · Santa Marta, Colombia · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · St. Georges, Grenada, West Indies · Castries, St. Lucia · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida

★ Bucket-list Panama Canal Miraflores Locks Private Expert Walking Tour of Kiel The Roman Theatre of Cartagena with the Rafael Mon…Ciudad Perdida +9 more

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from $9,749

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Explora Journeys · EXPLORA IIIOne-way

Caribbean 17 nights Apr 5, 2027 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Gustavia, St. Barts · … · Miami, Florida6 ports

San Juan, Puerto Rico · Gustavia, St. Barts · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Key West, Florida · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Open-Top Mini Moke Island Tour of St. Barts Soufrière Hills Volcano Exclusion Zone Helicopter…Mt. Liamuiga Volcano Crater Hike +2 more

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from $4,760

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Regent · Seven Seas PrestigeOne-way

Bermuda 14 nights Apr 9 – Apr 23, 2027 from Miami, Florida to New York, New York

Miami, Florida · Willis Island · … · New York, New York13 ports

Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Castries, St. Lucia · Gustavia, St. Barts · San Juan, Puerto Rico · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · New York, New York

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis Island The Natural Pool Private Full-Day Curaçao Island Tour with Local Ex… +7 more

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from $10,149

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Regent · Seven Seas MarinerOne-way

Caribbean 14 nights Apr 15 – Apr 29, 2027 from Miami, Florida to New York, New York

Miami, Florida · Willis Island · … · New York, New York12 ports

Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · St. John's, Antigua · Tortola, B.V.I. · Willis Island · New York, New York

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis Island The Natural Pool Private Full-Day Curaçao Island Tour with Local Ex… +6 more

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from $9,299

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Windstar · Star PrideRound-trip

Mediterranean 14 nights Nov 1 – Nov 15, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico14 ports

San Juan, Puerto Rico · Cruz Bay, St. John · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Les Saintes, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike Private Open-Top Mini Moke Island Tour of St. Barts +8 more

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from $3,902

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Explora Journeys · EXPLORA IVOne-way

Caribbean 8 nights Nov 5, 2027 from Miami, Florida to San Juan, Puerto Rico

Miami, Florida · Providenciales, Turks & Caicos · … · San Juan, Puerto Rico7 ports

Miami, Florida · Providenciales, Turks & Caicos · Gustavia, St. Barts · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Saint John/cruz Bay · San Juan, Puerto Rico

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & Reef Private Open-Top Mini Moke Island Tour of St. Barts Death in Paradise Filming Locations & Botanical Ga… +2 more

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from $4,725

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Windstar · Star PrideRound-trip

Mediterranean 14 nights Nov 8 – Nov 22, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico14 ports

San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Les Saintes, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico · Cruz Bay, St. John · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Grenada Private Taxi Tour Tobago Cays & Mystique Full-Day Private Sail Salt Whistle Bay +8 more

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from $4,084

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Seabourn · Seabourn QuestRound-trip

Caribbean 10 nights Nov 13 – Nov 23, 2027 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports

Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Gustavia, St. Barts · Great Harbor, Peter Island, BVI · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike Soufrière Hills Volcano Exclusion Zone Helicopter… +2 more

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from $4,504

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Windstar · Star PrideRound-trip

Caribbean 7 nights Nov 15 – Nov 22, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Cruz Bay, St. John · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike Private Open-Top Mini Moke Island Tour of St. Barts +3 more

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from $2,443

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Oceania · Oceania SirenaRound-trip

Mexico 31 nights Nov 21 – Dec 22, 2027 from Miami, Florida

Miami, Florida · Cozumel, Mexico · … · Miami, Florida23 ports

Miami, Florida · Cozumel, Mexico · Roatan, Honduras · Harvest Caye, Belize · Costa Maya, Mexico · Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · Miami, Florida · Nassau, Bahamas · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…El Cielo + Palancar + Columbia 3-Stop Snorkel Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Lamanai Mayan Ruins +16 more

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from $8,299

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Seabourn · Seabourn QuestRound-trip

Caribbean 11 nights Nov 23 – Dec 4, 2027 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Gustavia, St. Barts · Little Bay, Montserrat, Leeward Islands · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Private Open-Top Mini Moke Island Tour of St. Barts Soufrière Hills Volcano Exclusion Zone Helicopter… +3 more

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from $4,504

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Explora Journeys · EXPLORA IVOne-way

Caribbean 7 nights Nov 27, 2027 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Gustavia, St. Barts · … · Miami, Florida7 ports

San Juan, Puerto Rico · Gustavia, St. Barts · Virgin Gorda, British Virgin Islands · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Nydri, Nisos Lefkada, Greece · Ocean Cay, Bahamas · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Open-Top Mini Moke Island Tour of St. Barts The Baths National Park Private Full-Day Boat Charter +3 more

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from $4,200

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Silversea · Silver DawnOne-way

Caribbean 14 nights Nov 27 – Dec 11, 2027 from Lisbon, Portugal to San Juan, Puerto Rico

Lisbon, Portugal · Funchal, Madeira, Portugal · … · San Juan, Puerto Rico7 ports

Lisbon, Portugal · Funchal, Madeira, Portugal · Santa Cruz de La Palma, Spain · Santa Cruz de Tenerife, Canary Islands · Mindelo, Cape Verde Island · Gustavia, St. Barts · San Juan, Puerto Rico

★ Bucket-list Sintra Pico do Arieiro to Pico Ruivo Tajogaite Volcano Teide National Park +3 more

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from $7,500

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Regent · Seven Seas GrandeurRound-trip

Caribbean 10 nights Nov 28 – Dec 8, 2027 from Miami, Florida

Miami, Florida · Willis Island · … · Miami, Florida10 ports

Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis Island The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls +4 more

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from $6,699

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Explora Journeys · EXPLORA IVRound-trip

Caribbean 9 nights Dec 4, 2027 from Miami, Florida

Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida7 ports

Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Saint John/cruz Bay · Gustavia, St. Barts · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Private Open-Top Mini Moke Island Tour of St. Barts +1 more

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from $5,160

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Seabourn · Seabourn QuestRound-trip

Caribbean 14 nights Dec 4 – Dec 18, 2027 from Miami, Florida

Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida11 ports

Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · Roseau, Dominica · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Road Bay, Anguilla · Great Harbor, Peter Island, BVI · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +6 more

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from $5,949

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Oceania · Oceania SirenaRound-trip

Bahamas 12 nights Dec 10 – Dec 22, 2027 from Miami, Florida

Miami, Florida · Nassau, Bahamas · … · Miami, Florida10 ports

Miami, Florida · Nassau, Bahamas · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim With the Wild Exuma Pigs The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls +5 more

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from $3,499

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Silversea · Silver DawnRound-trip

Caribbean 10 nights Dec 11 – Dec 21, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico11 ports

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Bequia, Grenadines · Castries, St. Lucia · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Catamaran Charter Mt. Liamuiga Volcano Crater Hike Private Open-Top Mini Moke Island Tour of St. Barts +6 more

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from $6,050

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Explora Journeys · EXPLORA IIOne-way

Caribbean 7 nights Dec 19, 2027 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · Miami, Florida6 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Pointe-a-Pitre, Guadeloupe · Gustavia, St. Barts · Saint John/cruz Bay · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Death in Paradise Filming Locations & Botanical Ga…Private Open-Top Mini Moke Island Tour of St. Barts +1 more

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from $4,815

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Regent · Seven Seas VoyagerRound-trip

Mediterranean 25 nights Dec 19 – Jan 13, 2028 from Miami, Florida

Miami, Florida · Willis Island · … · Miami, Florida26 ports

Miami, Florida · Willis Island · Tortola, B.V.I. · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Oranjestad, Sint Eustatius · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Willis Island · Cartagena, Spain · Panama Canal, Panama · Colon, Panama · Puerto Limon, Costa Rica · Willis Island · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis Island Jost Van Dyke Private Full-Day Boat Charter +17 more

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from $13,149

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Oceania · Oceania MarinaRound-trip

Bahamas 17 nights Dec 20 – Jan 6, 2028 from Miami, Florida

Miami, Florida · Costa Maya, Mexico · … · Miami, Florida14 ports

Miami, Florida · Costa Maya, Mexico · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Miami, Florida · Nassau, Bahamas · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Chacchoben Mayan Ruins Great Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +8 more

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from $5,499

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Oceania · Oceania MarinaRound-trip

Caribbean 10 nights Dec 27 – Jan 6, 2028 from Miami, Florida

Miami, Florida · Nassau, Bahamas · … · Miami, Florida9 ports

Miami, Florida · Nassau, Bahamas · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim With the Wild Exuma Pigs Walk El Morro & Old San Juan's City Walls Jost Van Dyke +4 more

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from $3,499

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Seabourn · Seabourn QuestRound-trip

Caribbean 10 nights Dec 28 – Jan 7, 2028 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports

Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Gustavia, St. Barts · Great Harbor, Peter Island, BVI · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike Soufrière Hills Volcano Exclusion Zone Helicopter… +2 more

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from $5,184

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Silversea · Silver SpiritRound-trip

Caribbean 13 nights Dec 28 – Jan 10, 2028 from Bridgetown, Barbados

Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados12 ports

Bridgetown, Barbados · St. Georges, Grenada, West Indies · Bequia, Grenadines · Castries, St. Lucia · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Fort-de-France, Martinique · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi Tour Tobago Cays & Mystique Full-Day Private Sail Cosol Tours +7 more

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from $7,550

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Silversea · Silver NovaRound-trip

Caribbean 11 nights Dec 29 – Jan 9, 2028 from Miami, Florida

Miami, Florida · Key West, Florida · … · Miami, Florida8 ports

Miami, Florida · Key West, Florida · St. Thomas, U.S. Virgin Islands · Sopers Hole · Gustavia, St. Barts · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Dry Tortugas National Park Private Catamaran Sail & Snorkel at Honeymoon Beac…The Baths of Virgin Gorda +3 more

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from $8,750

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Explora Journeys · EXPLORA IIOne-way

Caribbean 7 nights Jan 2, 2028 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · Miami, Florida6 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Pointe-a-Pitre, Guadeloupe · Gustavia, St. Barts · Ocean Cay, Bahamas · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Death in Paradise Filming Locations & Botanical Ga…Private Open-Top Mini Moke Island Tour of St. Barts +2 more

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from $4,020

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Silversea · Silver RayRound-trip

Caribbean 12 nights Jan 3 – Jan 15, 2028 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida9 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +4 more

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from $7,550

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Silversea · Silver DawnRound-trip

Caribbean 11 nights Jan 4 – Jan 15, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico10 ports

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Catamaran Charter Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +5 more

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from $5,950

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Regent · Seven Seas GrandeurOne-way

Caribbean 10 nights Jan 5 – Jan 15, 2028 from Miami, Florida to Bridgetown, Barbados

Miami, Florida · Willis Island · … · Bridgetown, Barbados10 ports

Miami, Florida · Willis Island · Tortola, B.V.I. · Gustavia, St. Barts · Philipsburg, St. Maarten · Pointe-a-Pitre, Guadeloupe · Roseau, Dominica · Fort-de-France, Martinique · Castries, St. Lucia · Bridgetown, Barbados

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis Island Jost Van Dyke Private Open-Top Mini Moke Island Tour of St. Barts +6 more

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from $6,749

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Silversea · Silver ShadowOne-way

Caribbean 10 nights Jan 5 – Jan 15, 2028 from Miami, Florida to Cartagena, Colombia

Miami, Florida · Jost Van Dyke, British Virgin Islands · … · Cartagena, Colombia6 ports

Miami, Florida · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Cartagena, Colombia

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Catamaran Charter Private Open-Top Mini Moke Island Tour of St. Barts Private Full-Day Curaçao Island Tour with Local Ex… +2 more

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from $6,000

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Regent · Seven Seas PrestigeRound-trip

Caribbean 10 nights Jan 7 – Jan 17, 2028 from Miami, Florida

Miami, Florida · Willis Island · … · Miami, Florida9 ports

Miami, Florida · Willis Island · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis Island Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +3 more

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from $7,749

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Silversea · Silver NovaRound-trip

Caribbean 11 nights Jan 9 – Jan 20, 2028 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls The Baths of Virgin Gorda Private Open-Top Mini Moke Island Tour of St. Barts +3 more

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from $7,550

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Silversea · Silver SpiritRound-trip

Caribbean 12 nights Jan 10 – Jan 22, 2028 from Bridgetown, Barbados

Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados11 ports

Bridgetown, Barbados · Bequia, Grenadines · Castries, St. Lucia · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private Sail Cosol Tours Klein Bonaire +6 more

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from $6,550

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Regent · Seven Seas GrandeurRound-trip

Caribbean 10 nights Jan 15 – Jan 25, 2028 from Bridgetown, Barbados

Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados11 ports

Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Fort-de-France, Martinique · Willis Island · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi Tour La Soufrière Volcano Summit Hike Cosol Tours +6 more

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from $7,499

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Silversea · Silver DawnRound-trip

Caribbean 10 nights Jan 15 – Jan 25, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico11 ports

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Canouan, St. Vincent · Castries, St. Lucia · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Catamaran Charter Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +5 more

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from $5,750

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Regent · Seven Seas PrestigeRound-trip

Caribbean 10 nights Jan 17 – Jan 27, 2028 from Miami, Florida

Miami, Florida · Willis Island · … · Miami, Florida10 ports

Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Philipsburg, St. Maarten · Gustavia, St. Barts · St. John's, Antigua · Tortola, B.V.I. · Willis Island · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis Island The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls +4 more

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from $7,699

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Silversea · Silver NovaRound-trip

Caribbean 11 nights Jan 20 – Jan 31, 2028 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls The Baths of Virgin Gorda Mt. Liamuiga Volcano Crater Hike +3 more

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from $7,550

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Explora Journeys · EXPLORA IVOne-way

Caribbean 7 nights Jan 22, 2028 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Gustavia, St. Barts · … · Miami, Florida7 ports

San Juan, Puerto Rico · Gustavia, St. Barts · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Nydri, Nisos Lefkada, Greece · Puerto Plata, Dominican Republic · Ocean Cay, Bahamas · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Open-Top Mini Moke Island Tour of St. Barts Private Full-Day Boat Charter Private Sailing Charter +3 more

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from $4,020

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Silversea · Silver SpiritRound-trip

Caribbean 7 nights Jan 22 – Jan 29, 2028 from Bridgetown, Barbados

Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports

Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Gustavia, St. Barts · Roseau, Dominica · St. Georges, Grenada, West Indies · Castries, St. Lucia · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private Sail Mount Pelée & Saint-Pierre Private Open-Top Mini Moke Island Tour of St. Barts +3 more

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from $4,950

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Explora Journeys · EXPLORA IIOne-way

Bahamas 7 nights Jan 23, 2028 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · Miami, Florida6 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Pointe-a-Pitre, Guadeloupe · Gustavia, St. Barts · Ocean Cay, Bahamas · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Death in Paradise Filming Locations & Botanical Ga…Private Open-Top Mini Moke Island Tour of St. Barts +2 more

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from $4,020

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Regent · Seven Seas GrandeurRound-trip

Caribbean 10 nights Jan 25 – Feb 4, 2028 from Bridgetown, Barbados

Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · … · Bridgetown, Barbados10 ports

Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…La Soufrière Volcano Summit Hike Cosol Tours Mount Pelée & Saint-Pierre +5 more

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from $6,349

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Silversea · Silver DawnRound-trip

Caribbean 11 nights Jan 25 – Feb 5, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico10 ports

San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Roseau, Dominica · Canouan, St. Vincent · St. Georges, Grenada, West Indies · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Catamaran Charter Private Open-Top Mini Moke Island Tour of St. Barts Boiling Lake Hike +4 more

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from $6,050

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