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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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
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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 Bermuda ×Mexico ×Visits St. Lucia × Clear all
Showing 19 of 19 sailings
Oceania · Oceania VistaRepositioning
Caribbean 14 nights Oct 28 – Nov 11, 2026 from New York, New York to Miami, Florida
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida10 ports
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Full-Day Boat CharterJost Van DykePrivate Half-Day Island Adventure & Trunk Bay Beach +6 more
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from $3,412
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Princess · Majestic PrincessRepositioning
Caribbean 12 nights Nov 7 – Nov 19, 2026 from New York, New York to Fort Lauderdale (Port Everglades), Florida
New York, New York · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida7 ports
New York, New York · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Curacao, Caribbean · Port of Oranjestad, Aruba, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Manhattan Helicopter TourMaho BeachMt. Liamuiga Volcano Crater HikeGros Piton Summit Hike +3 more
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from $811
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Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Nov 8 – Nov 22, 2026 from Boston, Massachusetts to New Orleans, Louisiana
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · … · New Orleans, Louisiana8 ports
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · St. Lucia, Caribbean · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Georgetown, Grand Cayman, Cayman Islands · New Orleans, Louisiana
★ Bucket-list Private Luxury Boston TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Gros Piton Summit HikeGrenada Private Taxi Tour +4 more
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from $970
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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' +4 more
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from $3,310
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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… +4 more
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from $3,389
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Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Apr 4 – Apr 18, 2027 from New Orleans, Louisiana to Boston, Massachusetts
New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · … · Boston, Massachusetts9 ports
New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · St. Lucia, Caribbean · Tortola, B.V.I. · Boston, Massachusetts
★ Bucket-list Steamboat NatchezStingray City SandbarArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +5 more
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from $1,726
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Regent · Seven Seas PrestigeOne-way
Bermuda 14 nights Apr 9 – Apr 23, 2027 from Miami, Florida to New York, New York
Miami, Florida · Willis Island · … · New York, New York13 ports
Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Castries, St. Lucia · Gustavia, St. Barts · San Juan, Puerto Rico · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · New York, New York
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex… +6 more
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from $10,199
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Princess · Regal PrincessRepositioning
Caribbean 14 nights Nov 6 – Nov 20, 2027 from New York, New York to Miami, Florida
New York, New York · St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
New York, New York · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeAdventure Antigua +5 more
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from $1,324
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Cunard · Queen Mary 2Round-trip
Caribbean 13 nights Nov 19 – Dec 2, 2027 from New York, New York
New York, New York · St. Thomas, U.S. Virgin Islands · … · New York, New York8 ports
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
★ Bucket-list Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeGros Piton Summit Hike +3 more
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from $1,899
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Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Nov 27 – Dec 8, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. John's, Antigua · St. Lucia, Caribbean · Philipsburg, St. Maarten · Philadelphia, Pennsylvania
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Half-Day Island Adventure & Trunk Bay BeachGros Piton Summit Hike +1 more
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from $927
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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 HikeGros Piton Summit Hike +3 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 HikeGros Piton Summit HikeSwim with wild green sea turtles + two shipwrecks… +3 more
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from $3,086
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Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Dec 23 – Jan 3, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Mt. Liamuiga Volcano Crater HikeGros Piton Summit HikePrivate Half-Day Island Adventure & Trunk Bay BeachWalk El Morro & Old San Juan's City Walls +1 more
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from $1,516
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Norwegian · Norwegian PearlRound-trip
Caribbean 12 nights Jan 3 – Jan 15, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania8 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · Bridgetown, Barbados · St. Lucia, Caribbean · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Random Wind 'Paradise Day Sail'Swim with wild green sea turtles + two shipwrecks…Gros Piton Summit HikePrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $885
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Oceania · Oceania SonataOne-way
Mexico 44 nights Jan 6 – Feb 19, 2028 from Los Angeles, California to Miami, Florida
Los Angeles, California · Ensenada, Mexico · … · Miami, Florida29 ports
Los Angeles, California · Ensenada, Mexico · Cabo San Lucas, Mexico · Acapulco, Mexico · Puerto Quetzal, Guatemala · Puntarenas, Costa Rica · Kiel Canal, Germany · Cartagena, Colombia · Georgetown, Grand Cayman, Cayman Islands · Miami, Florida · Philipsburg, St. Maarten · Fort-de-France, Martinique · Castries, St. Lucia · St. Georges, Grenada, West Indies · Port of Oranjestad, Aruba, Caribbean · Miami, Florida · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Pointe-a-Pitre, Guadeloupe · Tortola, B.V.I. · Miami, Florida · Kiel Canal, Germany · Cozumel, Mexico · Roatan, Honduras · Harvest Caye, Belize · Costa Maya, Mexico · Kiel Canal, Germany · Miami, Florida
★ Bucket-list Warner Bros. Studio Tour HollywoodValle de Guadalupe wine countryEl Arco & Lover's BeachLa Quebrada Cliff Divers +19 more
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from $20,599
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Norwegian · Norwegian PearlRound-trip
Caribbean 12 nights Jan 15 – Jan 27, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania8 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · St. Lucia, Caribbean · Bridgetown, Barbados · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Random Wind 'Paradise Day Sail'Gros Piton Summit HikeSwim with wild green sea turtles + two shipwrecks…Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $885
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Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Jan 27 – Feb 7, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · St. John's, Antigua · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · St. John's, Antigua · St. Lucia, Caribbean · Philipsburg, St. Maarten · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Private Half-Day Island Adventure & Trunk Bay BeachGros Piton Summit HikeRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
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from $831
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Feb 7 – Feb 18, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · St. Lucia, Caribbean · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Random Wind 'Paradise Day Sail'Gros Piton Summit HikePrivate Half-Day Island Adventure & Trunk Bay BeachWalk El Morro & Old San Juan's City Walls +1 more
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from $831
Book This Cruise@ Cruisebound
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 HikeGros Piton Summit HikeSwim with wild green sea turtles + two shipwrecks… +3 more
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from $15,039
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 Costa Norwegian AmaWaterways Princess Celebrity Viking Ocean Avalon Disney Holland America Oceania Virgin Voyages Regent Cunard Seabourn Azamara