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 36 of 87 sailings
Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Nov 5 – Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $5,399
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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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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Nov 15 – Nov 25, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $4,999
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Princess · Majestic PrincessRepositioning
Caribbean 33 nights Nov 19 – Dec 22, 2026 from Fort Lauderdale (Port Everglades), Florida to San Antonio, Santiago, Chile
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · San Antonio, Santiago, Chile16 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · St. Lucia, Caribbean · Bridgetown, Barbados · Fortaleza, Brazil · Rio de Janeiro, Brazil · Montevideo, Uruguay · Buenos Aires, Argentina · Montevideo, Uruguay · Puerto Madryn, Argentina · Stanley, Falkland Islands · Ushuaia, Argentina · Cockburn And Beagle Channels · Punta Arenas, Chile · Puerto Montt, Chile · San Antonio, Santiago, Chile
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachGros Piton Summit HikeSwim with wild green sea turtles + two shipwrecks… +10 more
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from $2,966
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Nov 25 – Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $5,199
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Princess · Island PrincessRound-trip
Caribbean 12 nights Nov 30 – Dec 12, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · St. Maarten, Netherlands Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowArubaKlein Curaçao Private Day TripGros Piton Summit Hike +3 more
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from $1,098
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Princess · Enchanted PrincessRound-trip
Caribbean 14 nights Dec 3 – Dec 17, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · Dominica, Caribbean · St. Lucia, Caribbean · Port of Spain, Trinidad · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachMt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +3 more
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from $1,503
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Dec 5 – Dec 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $5,599
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Viking Ocean · Viking SeaRound-trip
Caribbean 21 nights Dec 15 – Jan 5, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Sail the Caribbean Sea · … · San Juan, Puerto Rico18 ports
San Juan, Puerto Rico · Sail the Caribbean Sea · Bridgetown, Barbados · Sail the Caribbean Sea · Iles du Salut, Guiana · Sail the Atlantic Ocean · Sail The Amazon River · Santarem, Brazil · Parintins, Brazil · Manaus, Brazil · Sail the Amazon River · Belem, Brazil · Sail the Atlantic Ocean · Scarborough, Tobago · Castries, St. Lucia · St. John's, Antigua · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsSwim with wild green sea turtles + two shipwrecks…ARC Transatlantic RallyCosol Tours +2 more
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from $12,499
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Princess · Coral PrincessRound-trip
Caribbean 11 nights Dec 26 – Jan 6, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Thomas, U.S. Virgin Islands · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · Bridgetown, Barbados · St. Lucia, Caribbean · St. Maarten, Netherlands Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks… +2 more
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from $1,199
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Princess · Crown PrincessRound-trip
Caribbean 14 nights Dec 27 – Jan 10, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +5 more
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from $1,914
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Jan 5 – Jan 15, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +5 more
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from $6,399
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Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 8 – Jan 15, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
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from $839
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Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 10 – Jan 17, 2027 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 · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +2 more
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from $618
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Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 15 – Jan 22, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Martinique · St. Georges, Grenada, West Indies · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsMaho BeachGrenada Private Taxi Tour +1 more
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from $960
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Jan 15 – Jan 25, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $6,099
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Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 17 – Jan 24, 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 · Martinique · St. Georges, Grenada, West Indies · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachGrenada Private Taxi TourGros Piton Summit Hike +1 more
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from $702
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Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 22 – Jan 29, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
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from $1,169
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Princess · Crown PrincessRound-trip
Caribbean 14 nights Jan 24 – Feb 7, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Guadeloupe, Caribbean · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +4 more
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from $1,142
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Jan 25 – Feb 4, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $6,099
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Feb 4 – Feb 14, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
View →
from $6,599
Book This Cruise@ Cruisebound
Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Feb 14 – Feb 24, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $6,299
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Feb 19 – Feb 26, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
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from $1,109
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 14 nights Feb 21 – Mar 7, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Martinique · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +4 more
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from $1,212
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Feb 24 – Mar 6, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $6,299
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 14 nights Feb 28 – Mar 14, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Martinique · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachBoiling Lake & Valley of DesolationGrenada Private Taxi Tour +4 more
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from $1,254
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Princess · Crown PrincessRound-trip
Caribbean 7 nights Mar 5 – Mar 12, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
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from $1,109
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Princess · Crown PrincessRound-trip
Caribbean 14 nights Mar 7 – Mar 21, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +5 more
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from $1,240
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Princess · Crown PrincessRound-trip
Caribbean 14 nights Mar 14 – Mar 28, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico13 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 · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +5 more
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from $1,886
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Princess · Crown PrincessRound-trip
Caribbean 7 nights Mar 19 – Mar 26, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
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from $919
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Princess · Crown PrincessRound-trip
Caribbean 7 nights Mar 21 – Mar 28, 2027 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 · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +2 more
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from $814
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Princess · Island PrincessRound-trip
Caribbean 10 nights Nov 5 – Nov 15, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Amber Cove, Dominican Republic · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Antigua, Antigua & Barbuda · St. Maarten, Netherlands Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live Show27 Charcos of DamajaguaWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $1,041
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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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Princess · Island PrincessRound-trip
Caribbean 14 nights Nov 15 – Nov 29, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Lucia, Caribbean · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachMt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +5 more
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from $1,109
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Princess · Emerald PrincessRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2027 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 · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +2 more
View →
from $796
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Nov 27 – Dec 7, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $4,299
Book This Cruise@ Cruisebound
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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