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
My result then click any cruise row to open it
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
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
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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 Falmouth Harbour × Clear all
Showing 7 of 7 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 · 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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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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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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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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Seabourn · Seabourn OvationRound-trip
Caribbean 21 nights Dec 18 – Jan 8, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados19 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port Elizabeth, Saint Vincent · Saint-Pierre, Newfoundland, Canada · Terre-de-haut, Guadeloupe · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Road Bay, Anguilla · Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Road Bay, Anguilla · Falmouth Harbour, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourSchotia Private Game ReserveÎle aux Marins +11 more
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from $11,312
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Seabourn · Seabourn OvationOne-way
Caribbean 11 nights Dec 28 – Jan 8, 2028 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados10 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Road Bay, Anguilla · Falmouth Harbour, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaPrivate Island HoppingAntigua Stingray City +6 more
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from $5,779
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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