Bucket-List Cruise Adventures

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Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

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Showing 14 of 14 sailings
Windstar · Star PrideRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
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 WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $2,411
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Windstar · Star LegendRound-trip
Mediterranean 7 nights Nov 27 – Dec 4, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Anses D'arlet, Martinique · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Anses D'arlet, Martinique · Rodney Bay, St. Lucia · Casablanca, Morocco · Mayreau, Grenadines · St. Georges, Grenada, West Indies · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Small-Boat Snorkel with Wild Sea Turtles, Anse NoireFull-Day Private Catamaran Sail to Soufrière & the…Private Guided Tour of Casablanca with Hassan II M… +3 more
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from $2,594
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Windstar · Star LegendOne-way
Caribbean 8 nights Dec 4 – Dec 12, 2026 from Bridgetown, Barbados to Port of Oranjestad, Aruba, Caribbean
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Port of Oranjestad, Aruba, Caribbean8 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Sca · Bequia, Grenadines · Mayreau, Grenadines · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Full-Day Private Catamaran Sail to Soufrière & the…Tobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +3 more
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from $2,940
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Windstar · Star PrideRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Deshaies, Guadeloupe · Marmaris, Turkey · 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 +2 more
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from $3,636
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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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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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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 Jan 3 – Jan 10, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Deshaies, Guadeloupe · Marmaris, Turkey · 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 +2 more
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from $4,896
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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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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 IlchulbongBoiling Lake HikeSalt Whistle Bay +3 more
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from $2,432
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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
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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 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 Mar 13 – Mar 20, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
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 WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $2,656
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Windstar · Star PrideRound-trip
Mediterranean 7 nights Mar 27 – Apr 3, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
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 WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $2,551
Book This Cruise@ Cruisebound

Itineraries from the Cruisebound catalog + our enrichment; schedules cross-checked against official port authorities. Booking via Cruisebound and CruiseDirect — we may earn a commission, at no extra cost to you.

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