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 2 selected · clear 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 Oceania Regent Seabourn Viking Ocean River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Filtering North America ×Northern Europe ×Visits St. Maarten × Clear all
Showing 15 of 15 sailings
Regent · Seven Seas SplendorOne-way
Australia & South Pacific 16 nights Oct 30 – Nov 15, 2026 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida14 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Willis Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Willis Island · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · San Juan, Puerto Rico · Willis Island · Miami, Florida
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgRandom Wind 'Paradise Day Sail' +5 more
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from $11,950
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Cunard · Queen Mary 2Round-trip
Northern Europe 25 nights Nov 10 – Dec 5, 2026 from Southampton, England
Southampton, England · New York, New York · … · Southampton, England8 ports
Southampton, England · New York, New York · St. Thomas, U.S. Virgin Islands · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Norman Island +2 more
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from $3,587
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Cunard · Queen Mary 2Repositioning
Northern Europe 21 nights Dec 12 – Jan 2, 2027 from Southampton, England to New York, New York
Southampton, England · New York, New York · … · New York, New York9 ports
Southampton, England · New York, New York · Road Town, Tortola, B.V.I. · Philipsburg, St. Maarten · Bridgetown, Barbados · St. Lucia, Caribbean · Dominica, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · New York, New York
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Manhattan Helicopter TourNorman IslandRandom Wind 'Paradise Day Sail' +2 more
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from $3,310
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Cunard · Queen ElizabethRepositioning
Mexico 33 nights Dec 17 – Jan 19, 2027 from Miami, Florida to Southampton, England
Miami, Florida · San Juan, Puerto Rico · … · Southampton, England16 ports
Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida · Praia da Vitoria, Portugal · Ponta Delgada, Azores, Portugal · Southampton, England
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsSwim with wild green sea turtles + two shipwrecks…Random Wind 'Paradise Day Sail' +5 more
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from $5,999
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Cunard · Queen Mary 2Repositioning
Northern Europe 23 nights Dec 19 – Jan 11, 2027 from New York, New York to Southampton, England
New York, New York · Road Town, Tortola, B.V.I. · … · Southampton, England9 ports
New York, New York · Road Town, Tortola, B.V.I. · Philipsburg, St. Maarten · Bridgetown, Barbados · St. Lucia, Caribbean · Dominica, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · New York, New York · Southampton, England
★ Bucket-list Manhattan Helicopter TourNorman IslandRandom Wind 'Paradise Day Sail'Swim with wild green sea turtles + two shipwrecks… +2 more
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from $3,389
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Cunard · Queen Mary 2Round-trip
Mediterranean 34 nights Jan 11 – Feb 14, 2027 from Southampton, England
Southampton, England · Funchal, Madeira, Portugal · … · Southampton, England12 ports
Southampton, England · Funchal, Madeira, Portugal · Road Town, Tortola, B.V.I. · Bridgetown, Barbados · St. Lucia, Caribbean · Grenada, Caribbean · Dominica, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Amber Cove, Dominican Republic · Philipsburg, St. Maarten · Santa Cruz de Tenerife, Canary Islands · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Pico do Arieiro to Pico RuivoNorman IslandSwim with wild green sea turtles + two shipwrecks… +4 more
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from $7,369
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Cunard · Queen Mary 2Round-trip
Northern Europe 27 nights Nov 12 – Dec 9, 2027 from Southampton, England
Southampton, England · New York, New York · … · Southampton, England10 ports
Southampton, England · New York, New York · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater Hike +2 more
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from $3,489
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Cunard · Queen Mary 2Repositioning
Northern Europe 20 nights Dec 14 – Jan 3, 2028 from Southampton, England to New York, New York
Southampton, England · New York, New York · … · New York, New York8 ports
Southampton, England · New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Manhattan Helicopter TourMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks… +1 more
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from $3,053
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Cunard · Queen Mary 2Repositioning
Northern Europe 21 nights Dec 21 – Jan 11, 2028 from New York, New York to Southampton, England
New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Southampton, England8 ports
New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York · Southampton, England
★ Bucket-list Manhattan Helicopter TourMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks…Random Wind 'Paradise Day Sail' +1 more
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from $3,086
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Cunard · Queen Mary 2Round-trip
Mediterranean 35 nights Jan 11 – Feb 15, 2028 from Southampton, England
Southampton, England · Santa Cruz de Tenerife, Canary Islands · … · Southampton, England13 ports
Southampton, England · Santa Cruz de Tenerife, Canary Islands · Philipsburg, St. Maarten · Grenada, Caribbean · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Funchal, Madeira, Portugal · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Teide National ParkRandom Wind 'Paradise Day Sail'Swim with wild green sea turtles + two shipwrecks… +5 more
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from $4,899
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Cunard · Queen Mary 2Round-trip
Northern Europe 28 nights Feb 27 – Mar 26, 2028 from Southampton, England
Southampton, England · New York, New York · … · Southampton, England9 ports
Southampton, England · New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Manhattan Helicopter TourMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks… +1 more
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from $4,859
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Cunard · Queen Mary 2Repositioning
Caribbean 20 nights Mar 6 – Mar 26, 2028 from New York, New York to Southampton, England
New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Southampton, England8 ports
New York, New York · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · Philipsburg, St. Maarten · New York, New York · Southampton, England
★ Bucket-list Manhattan Helicopter TourMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks…Random Wind 'Paradise Day Sail' +1 more
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from $15,039
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MSC Cruises · MSC MeravigliaRepositioning
Mediterranean 20 nights Apr 18 – May 8, 2028 from Bridgetown, Barbados to Southampton, England
Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · … · Southampton, England11 ports
Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · Ponta Delgada, Azores, Portugal · Lisbon, Portugal · Vigo, Spain · Le Havre (Paris), France · Southampton, England
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourMount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga… +4 more
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from $1,569
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MSC Cruises · MSC MeravigliaRepositioning
Caribbean 15 nights Apr 22 – May 7, 2028 from Fort-de-France, Martinique to Le Havre (Paris), France
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · … · Le Havre (Paris), France7 ports
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · Ponta Delgada, Azores, Portugal · Lisbon, Portugal · Vigo, Spain · Le Havre (Paris), France
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Random Wind 'Paradise Day Sail'Sintra +1 more
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from $1,210
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MSC Cruises · MSC MeravigliaRepositioning
Caribbean 14 nights Apr 23 – May 7, 2028 from Pointe-a-Pitre, Guadeloupe to Le Havre (Paris), France
Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · … · Le Havre (Paris), France6 ports
Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · Ponta Delgada, Azores, Portugal · Lisbon, Portugal · Vigo, Spain · Le Havre (Paris), France
★ Bucket-list Death in Paradise Filming Locations & Botanical Ga…Random Wind 'Paradise Day Sail'SintraPrivate Paris Highlights & Seine River Cruise from…
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from $1,111
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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.

19 lines
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MSC Cruises Royal Caribbean Carnival Viking River Costa Norwegian AmaWaterways Princess Celebrity Viking Ocean Avalon Disney Holland America Oceania Virgin Voyages Regent Cunard Seabourn Azamara