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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Filtering Celebrity ×Royal Caribbean ×Visits Port of Kingstown × Clear all
Showing 17 of 17 sailings
Celebrity · Celebrity ConstellationRound-trip
Caribbean 11 nights Nov 17 – Nov 28, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · Fort-de-France, Martinique · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachCosol Tours +5 more
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from $917
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Jan 17 – Jan 24, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Fort-de-France, Martinique · Port of Kingstown, St. Vincent & the Grenadines · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachMount Pelée & Saint-Pierre +2 more
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from $584
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Celebrity · Celebrity EclipseRound-trip
Caribbean 10 nights Jan 29 – Feb 8, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. John's, Antigua · … · Fort Lauderdale (Port Everglades), Florida7 ports
Fort Lauderdale (Port Everglades), Florida · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Half-Day Island Adventure & Trunk Bay BeachCosol ToursSwim with wild green sea turtles + two shipwrecks… +2 more
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from $1,237
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Feb 28 – Mar 7, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Fort-de-France, Martinique · Port of Kingstown, St. Vincent & the Grenadines · St. Georges, Grenada, West Indies · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay BeachMount Pelée & Saint-Pierre +2 more
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from $573
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Celebrity · Celebrity EclipseRound-trip
Caribbean 10 nights Mar 12 – Mar 22, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. John's, Antigua · … · Fort Lauderdale (Port Everglades), Florida7 ports
Fort Lauderdale (Port Everglades), Florida · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Half-Day Island Adventure & Trunk Bay BeachCosol ToursSwim with wild green sea turtles + two shipwrecks… +2 more
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from $1,321
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Royal Caribbean · Grandeur of the SeasOne-way
Caribbean 7 nights Apr 24 – May 1, 2027 from Colon, Panama to San Juan, Puerto Rico
Colon, Panama · Port of Kingstown, St. Vincent & the Grenadines · … · San Juan, Puerto Rico6 ports
Colon, Panama · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Panama Canal Full TransitLa Soufrière Volcano Summit HikeCosol ToursPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $539
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Celebrity · Celebrity SummitRound-trip
Caribbean 9 nights Oct 29 – Nov 7, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. John's, Antigua · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · St. John's, Antigua · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Half-Day Island Adventure & Trunk Bay BeachCosol ToursGrenada Private Taxi Tour +3 more
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from $879
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Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Nov 14 – Nov 21, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Kingstown, St. Vincent & the Grenadines · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsLa Soufrière Volcano Summit HikeSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $504
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Bridgetown, Barbados · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port of Kingstown, St. Vincent & the Grenadines · St. John's, Antigua · Charlotte Amalie, 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…Grenada Private Taxi TourLa Soufrière Volcano Summit Hike +2 more
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from $738
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Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Kingstown, St. Vincent & the Grenadines · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · Fort-de-France, Martinique · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsLa Soufrière Volcano Summit HikeSwim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more
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from $643
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Celebrity · Celebrity EclipseRound-trip
Caribbean 13 nights Dec 23 – Jan 5, 2028 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · … · Fort Lauderdale (Port Everglades), Florida9 ports
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Port of Kingstown, St. Vincent & the Grenadines · Roseau, Dominica · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +4 more
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from $2,433
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 8 nights Dec 31 – Jan 8, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · St. John's, Antigua · Port of Kingstown, St. Vincent & the Grenadines · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefMt. Liamuiga Volcano Crater Hike +3 more
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from $1,131
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Jan 23 – Jan 30, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Kingstown, St. Vincent & the Grenadines · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Port of Kingstown, St. Vincent & the Grenadines · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsLa Soufrière Volcano Summit HikeGrenada Private Taxi TourMount Pelée & Saint-Pierre +2 more
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from $628
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Jan 30 – Feb 6, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Bridgetown, Barbados · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port of Kingstown, St. Vincent & the Grenadines · St. John's, Antigua · Charlotte Amalie, 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…Grenada Private Taxi TourLa Soufrière Volcano Summit Hike +2 more
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from $639
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Feb 6 – Feb 13, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Bridgetown, Barbados · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Bridgetown, Barbados · Roseau, Dominica · Port of Kingstown, St. Vincent & the Grenadines · St. John's, Antigua · Charlotte Amalie, 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…Boiling Lake HikeLa Soufrière Volcano Summit Hike +2 more
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from $647
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Feb 13 – Feb 20, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Roseau, Dominica · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Roseau, Dominica · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsBoiling Lake HikeSwim with wild green sea turtles + two shipwrecks…La Soufrière Volcano Summit Hike +2 more
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from $640
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Apr 2 – Apr 9, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Port of Kingstown, St. Vincent & the Grenadines · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay BeachLa Soufrière Volcano Summit Hike +2 more
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from $750
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