Bucket-List Cruise Adventures

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Showing 36 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 BeachPrivate Catamaran Sail & SnorkelRandom 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 WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. 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 WallsNorman IslandMt. Liamuiga Volcano Crater HikePrivate 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 WallsTrunk 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 & ReefThe full 27 jumps at the Damajagua WaterfallsSaona 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 WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater HikePrivate 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 WallsTrunk 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 WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia 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 CharterRandom 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 ToursBoiling Lake HikeMt. 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 WallsNorman IslandMt. Liamuiga Volcano Crater HikePrivate 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 IslandWalk El Morro & Old San Juan's City WallsPrivate 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 WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. 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 WallsTrunk 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 CharterPrivate Open-Top Mini Moke Island Tour of St. BartsRandom 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 SailMount Pelée & Saint-PierreJardin 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 BeachPrivate Catamaran Sail & SnorkelPrivate 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 CharterPrivate Open-Top Mini Moke Island Tour of St. BartsPrivate 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 GardensZodiac Circumnavigation of Willis IslandMartha Brae River Bamboo RaftingBlue 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 WallsTrunk 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 ToursBoiling Lake HikeMt. 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 CharterRandom 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 WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. 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 WallsPrivate Full-Day Boat CharterThe Baths National ParkPrivate 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 WallsMt. Liamuiga Volcano Crater HikeNorman IslandPrivate 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. BartsSeongsan IlchulbongBoiling 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 WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. 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 CharterRandom 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 CityPrivate Island HoppingThe 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 WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsBarbuda'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 WallsThe Baths National ParkPrivate Open-Top Mini Moke Island Tour of St. BartsRandom 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. BartsPrivate Half-Day Island Adventure & Trunk Bay BeachNorman 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 WallsTrunk 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 IlchulbongSail Into the Bay of Les Saintes at DawnSalt 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 WallsPrivate Catamaran CharterPrivate Open-Top Mini Moke Island Tour of St. BartsBarbuda'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 WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts +3 more
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from $4,928
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