Bucket-List Cruise Adventures

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Showing 36 of 48 sailings
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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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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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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Silversea · Silver ShadowOne-way
Caribbean 10 nights Dec 10 – Dec 20, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico9 ports
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Iles des Saintes, Guadeloupe · Fort-de-France, Martinique · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Trunk Bay Underwater Snorkel Trail & VI National P…Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +5 more
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from $3,850
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Explora Journeys · EXPLORA IIIRound-trip
Caribbean 15 nights Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Bay, Anguilla · … · San Juan, Puerto Rico12 ports
San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Grand Turk, Turks and Caicos · Miami, Florida · Ocho Rios, Jamaica · Ain Sokhna, Egypt · Jost Van Dyke, British Virgin Islands · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Island HoppingPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +7 more
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from $12,600
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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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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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Explora Journeys · EXPLORA IIIRound-trip
Caribbean 16 nights Dec 20, 2026 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · … · Miami, Florida13 ports
Miami, Florida · Ocho Rios, Jamaica · Ain Sokhna, Egypt · Jost Van Dyke, British Virgin Islands · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · St. John's, Antigua · Pointe-a-Pitre, Guadeloupe · Saint John/cruz Bay · Samana, Dominican Republic · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HolePrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Catamaran Charter +7 more
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from $13,235
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Silversea · Silver ShadowRound-trip
Caribbean 7 nights Dec 20 – Dec 27, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Little Bay, Montserrat, Leeward Islands · Castries, St. Lucia · Fort-de-France, Martinique · Sopers Hole · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran CharterSoufrière Hills Volcano Exclusion Zone Helicopter…Cosol Tours +2 more
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from $5,950
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Explora Journeys · EXPLORA IOne-way
Caribbean 8 nights Dec 27, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico8 ports
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 Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Catamaran Charter +3 more
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from $7,095
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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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Silversea · Silver NovaOne-way
Caribbean 8 nights Dec 29 – Jan 6, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Charlestown, Nevis, St. Kitts and Nevis · Roseau, Dominica · Codrington, Barbuda · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Island TourBoiling Lake Hike +3 more
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from $6,850
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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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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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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 HoppingPrivate Catamaran CharterThe Baths of Virgin Gorda +3 more
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from $3,638
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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 WallsTrunk 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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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 WallsPrivate Catamaran CharterPrivate Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +7 more
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from $5,750
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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 SailGrenada Private Taxi TourCosol Tours +7 more
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from $7,450
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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 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 $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 GordaPrivate Catamaran CharterThe Baths National Park +3 more
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from $3,008
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Silversea · Silver ShadowOne-way
Mediterranean 14 nights Mar 9 – Mar 23, 2027 from San Juan, Puerto Rico to Lisbon, Portugal
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · Lisbon, Portugal6 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Codrington, Barbuda · Santa Cruz de La Palma, Spain · Santa Cruz de Tenerife, Canary Islands · Lisbon, Portugal
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran CharterBarbuda's Pink Sand Beach at Dawn, Private & EmptyTajogaite Volcano +2 more
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from $7,000
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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 CityPrivate Island HoppingPrivate Catamaran Charter +3 more
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from $2,868
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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 WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts +8 more
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from $3,902
Book This Cruise@ Cruisebound
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 WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +8 more
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from $4,084
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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 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 $2,443
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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 WallsPrivate Catamaran CharterMt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts +6 more
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from $6,050
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Silversea · Silver DawnRound-trip
Caribbean 7 nights Dec 21 – Dec 28, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Codrington, Barbuda · 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…Mt. Liamuiga Volcano Crater HikeCosol Tours +2 more
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from $5,150
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Explora Journeys · EXPLORA IIOne-way
Caribbean 7 nights Dec 26, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Miami, Florida · Puerto Plata, Dominican Republic · Ain Sokhna, Egypt · Frederikstad, St. Croix · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Full-Day Boat Charter +2 more
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from $5,350
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Silversea · Silver RayOne-way
Caribbean 8 nights Dec 26 – Jan 3, 2028 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · 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 Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Barbuda's Pink Sand Beach at Dawn, Private & EmptyMount Pelée & Saint-Pierre +3 more
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from $7,050
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Silversea · Silver DawnRound-trip
Caribbean 7 nights Dec 28 – Jan 4, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Philipsburg, St. Maarten · Roseau, Dominica · 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…Random Wind 'Paradise Day Sail'Boiling Lake Hike +2 more
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from $5,350
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