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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Showing 25 of 25 sailings
Carnival · Carnival VeneziaRound-trip
Caribbean Oct 18, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · … · Port Canaveral, Florida10 ports
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · Antigua, Antigua & Barbuda · Fort-de-France, Martinique · Grenada, Caribbean · Kingstown, St. Vincent (dock) · Bridgetown, Barbados · Philipsburg, St. Maarten · San Juan, Puerto Rico · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Adventure AntiguaMount Pelée & Saint-Pierre +3 more
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from $994
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Oct 31, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Willemstad, Curacao · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Curaçao Island Tour with Local Ex…ArubaMount Pelée & Saint-Pierre +1 more
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from $1,253
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Nov 7, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $1,755
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
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from $1,253
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 12, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $1,335
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 19, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeMount Pelée & Saint-PierreAruba +1 more
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from $1,183
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 26, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Fort-de-France, Martinique · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachMount Pelée & Saint-PierreSwim with wild green sea turtles + two shipwrecks… +2 more
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from $2,039
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 9, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
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from $1,190
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 16, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $1,271
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 29, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Fort-de-France, Martinique · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +2 more
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from $1,519
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Carnival · Carnival FirenzeRepositioning
Caribbean Feb 2, 2027 from Buenos Aires, Argentina to Miami, Florida
Buenos Aires, Argentina · Rio de Janeiro, Brazil · … · Miami, Florida8 ports
Buenos Aires, Argentina · Rio de Janeiro, Brazil · Maceio, Brazil (dock) · Crossing The Equator (dock) · Grenada, Caribbean · Fort-de-France, Martinique · Philipsburg, St. Maarten · Miami, Florida
★ Bucket-list El Teatro ColónPrivate Full-Day Rio HighlightsLine-Crossing CeremonyMount Pelée & Saint-Pierre +2 more
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from $1,756
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Feb 27, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
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from $1,260
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Carnival · Carnival FirenzeRound-trip
Caribbean Mar 22, 2027 from Miami, Florida
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida9 ports
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Grenada, Caribbean · Bridgetown, Barbados · Fort-de-France, Martinique · Antigua, Antigua & Barbuda · Philipsburg, St. Maarten · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…ArubaKlein Curaçao Private Day TripSwim with wild green sea turtles + two shipwrecks… +3 more
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from $627
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Apr 3, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
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from $1,258
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Carnival · Carnival PrideRound-trip
Caribbean Nov 28, 2027 from Baltimore, Maryland
Baltimore, Maryland · Philipsburg, St. Maarten · … · Baltimore, Maryland7 ports
Baltimore, Maryland · Philipsburg, St. Maarten · Fort-de-France, Martinique · Bridgetown, Barbados · St. Lucia, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Baltimore, Maryland
★ Bucket-list Random Wind 'Paradise Day Sail'Mount Pelée & Saint-PierreSwim with wild green sea turtles + two shipwrecks…Gros Piton Summit Hike +1 more
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from $1,142
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Carnival · Carnival ConquestRound-trip
Caribbean Nov 29, 2027 from Miami, Florida
Miami, Florida · St. Thomas, U.S. Virgin Islands · … · Miami, Florida8 ports
Miami, Florida · St. Thomas, U.S. Virgin Islands · Guadeloupe, Caribbean · St. Lucia, Caribbean · Fort-de-France, Martinique · Philipsburg, St. Maarten · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Catamaran Sail & Snorkel at Honeymoon Beac…Gros Piton Summit HikeMount Pelée & Saint-Pierre +2 more
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from $778
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Dec 26, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Fort-de-France, Martinique · St. John's, Antigua · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more
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from $1,846
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Carnival · Carnival MiracleRound-trip
Caribbean Jan 15, 2028 from Baltimore, Maryland
Baltimore, Maryland · St. Croix, U.S. Virgin Islands · … · Baltimore, Maryland7 ports
Baltimore, Maryland · St. Croix, U.S. Virgin Islands · Antigua, Antigua & Barbuda · Fort-de-France, Martinique · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Baltimore, Maryland
★ Bucket-list Buck Island ReefAdventure AntiguaMount Pelée & Saint-PierreRandom Wind 'Paradise Day Sail' +1 more
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from $1,107
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Carnival · Carnival FirenzeRound-trip
Caribbean Jan 23, 2028 from Port Canaveral, Florida
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · … · Port Canaveral, Florida10 ports
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · Antigua, Antigua & Barbuda · Guadeloupe, Caribbean · Fort-de-France, Martinique · Grenada, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · San Juan, Puerto Rico · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Adventure AntiguaMount Pelée & Saint-Pierre +3 more
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from $865
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Jan 29, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more
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from $979
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Carnival · Carnival FirenzeRound-trip
Caribbean Feb 6, 2028 from Port Canaveral, Florida
Port Canaveral, Florida · Grand Turk, Turks and Caicos · … · Port Canaveral, Florida10 ports
Port Canaveral, Florida · Grand Turk, Turks and Caicos · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · St. Lucia, Caribbean · Bridgetown, Barbados · Fort-de-France, Martinique · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexGibbs Cay Private Stingray Swim & Reef SnorkelArubaKlein Curaçao Private Day Trip +5 more
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from $879
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Feb 26, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more
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from $1,056
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Mar 11, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Bridgetown, Barbados · Fort-de-France, Martinique · Roseau, Dominica · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Swim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more
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from $1,127
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Mar 25, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more
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from $1,119
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Carnival · Carnival FirenzeRound-trip
Caribbean Apr 2, 2028 from Port Canaveral, Florida
Port Canaveral, Florida · Amber Cove, Dominican Republic · … · Port Canaveral, Florida10 ports
Port Canaveral, Florida · Amber Cove, Dominican Republic · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · St. Lucia, Caribbean · Bridgetown, Barbados · Fort-de-France, Martinique · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor Complex27 Charcos of DamajaguaArubaKlein Curaçao Private Day Trip +5 more
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from $903
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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