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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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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Showing 15 of 15 sailings
Norwegian · Norwegian SunOne-way
Bermuda 13 nights Oct 24 – Nov 6, 2026 from New York, New York to Miami, Florida
New York, New York · Royal Naval Dockyard, Bermuda · … · Miami, Florida10 ports
New York, New York · Royal Naval Dockyard, Bermuda · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Cabo Rojo, Dominican Republic · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of BermudaWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac… +5 more
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from $1,257
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Princess · Crown PrincessOne-way
Caribbean 8 nights Dec 19 – Dec 27, 2026 from Fort Lauderdale (Port Everglades), Florida to San Juan, Puerto Rico
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Antigua, Antigua & Barbuda · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowArubaPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City Walls
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from $515
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Princess · Crown PrincessOne-way
Caribbean 5 nights Jan 3 – Jan 8, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · Bridgetown, Barbados6 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeGrenada Private Taxi Tour +1 more
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from $474
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Regent · Seven Seas MarinerOne-way
Caribbean 18 nights Jan 4 – Jan 22, 2027 from Miami, Florida to Rio de Janeiro, Brazil
Miami, Florida · Willis Island · … · Rio de Janeiro, Brazil17 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · Willis Island · Devils Island, French Guiana · Willis Island · Belem, Brazil · Willis Island · Recife, Brazil · Maceio, Brazil · Bahia de Salvador, Brazil · Willis Island · Buzios, Brazil · Rio de Janeiro, Brazil
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay Beach +3 more
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from $12,760
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Azamara · Azamara JourneyOne-way
Caribbean 11 nights Jan 14 – Jan 25, 2027 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Saint John, New Brunswick · … · Bridgetown, Barbados10 ports
Miami, Florida · Saint John, New Brunswick · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $3,116
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Oceania · Oceania AlluraOne-way
Caribbean 7 nights Feb 5 – Feb 12, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico6 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Gustavia, St. Barts · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +1 more
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from $3,375
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Regent · Seven Seas PrestigeOne-way
Caribbean 10 nights Mar 20 – Mar 30, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Willis Island · … · San Juan, Puerto Rico10 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Roseau, Dominica · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterBoiling Lake Hike +6 more
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from $6,099
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Regent · Seven Seas PrestigeOne-way
Bahamas 10 nights Mar 30 – Apr 9, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Tortola, B.V.I. · … · Miami, Florida11 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · La Romana, Dominican Republic · Willis Island · Nassau, Bahamas · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikePrivate Half-Day Island Adventure & Trunk Bay Beach +6 more
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from $6,049
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Royal Caribbean · Vision of the SeasOne-way
Caribbean 10 nights Apr 4 – Apr 14, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +5 more
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from $792
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Azamara · Azamara QuestOne-way
Caribbean 17 nights Oct 28 – Nov 14, 2027 from New York, New York to Bridgetown, Barbados
New York, New York · Hamilton, Bermuda · … · Bridgetown, Barbados13 ports
New York, New York · Hamilton, Bermuda · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Manhattan Helicopter TourRandom Wind 'Paradise Day Sail'Norman IslandWalk El Morro & Old San Juan's City Walls +4 more
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from $5,583
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Norwegian · Norwegian PrimaOne-way
Caribbean 10 nights Nov 3 – Nov 13, 2027 from New York, New York to San Juan, Puerto Rico
New York, New York · Royal Naval Dockyard, Bermuda · … · San Juan, Puerto Rico9 ports
New York, New York · Royal Naval Dockyard, Bermuda · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. John's, Antigua · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of BermudaJost Van DykeMt. Liamuiga Volcano Crater Hike +5 more
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from $1,554
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Royal Caribbean · Grandeur of the SeasOne-way
Panama Canal 7 nights Nov 27 – Dec 4, 2027 from San Juan, Puerto Rico to Colon, Panama
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Colon, Panama6 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Willemstad, Curacao · Colon, Panama
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Cosol Tours +2 more
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from $597
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Azamara · Azamara QuestOne-way
Caribbean 7 nights Nov 28 – Dec 5, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico8 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 · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +3 more
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from $2,449
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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 BeachThe Roman Theatre of Cartagena with the Rafael Mon… +16 more
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from $20,599
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Regent · Seven Seas PrestigeOne-way
Mediterranean 12 nights Mar 14 – Mar 26, 2028 from Panama City, Panama to Miami, Florida
Panama City, Panama · Kiel Canal, Germany · … · Miami, Florida12 ports
Panama City, Panama · Kiel Canal, Germany · Cartagena, Spain · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Willis Island · St. Georges, Grenada, West Indies · Roseau, Dominica · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Willis Island · Miami, Florida
★ Bucket-list The Roman Theatre of Cartagena with the Rafael Mon…Zodiac Circumnavigation of Willis IslandThe Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex… +4 more
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from $8,599
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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 Costa Norwegian AmaWaterways Princess Celebrity Viking Ocean Avalon Disney Holland America Oceania Virgin Voyages Regent Cunard Seabourn Azamara