Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

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

When are you free? — only cruises that fit entirely inside your dates
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Where to? tap as many as you like Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
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Luxury Azamara Explora Journeys Oceania Regent Seabourn Silversea Viking Ocean Windstar River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Filtering Visits Les Saintes × Clear all
Showing 9 of 9 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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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 · 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 · 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
Book This Cruise@ Cruisebound
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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MSC Cruises Royal Caribbean Carnival Viking River Norwegian AmaWaterways Costa Princess Celebrity Avalon Disney Viking Ocean Holland America Silversea Oceania Virgin Regent Explora Journeys Cunard Azamara Windstar Seabourn Virgin Voyages