Bucket-List Cruise Adventures

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Showing 20 of 20 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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Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2026 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 · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $603
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Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Dec 26 – Jan 2, 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 · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $817
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Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Jan 9 – Jan 16, 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 · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · St. Georges, Grenada, West Indies · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $517
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Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Jan 23 – Jan 30, 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 · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $501
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Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Feb 6 – Feb 13, 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 · Roseau, Dominica · Castries, St. Lucia · 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 BeachBoiling Lake Hike +2 more
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from $550
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Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Feb 20 – Feb 27, 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 · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $723
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Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Mar 6 – Mar 13, 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 · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $884
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Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Mar 20 – Mar 27, 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 · Roseau, Dominica · Castries, St. Lucia · 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 BeachBoiling Lake Hike +2 more
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from $684
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Celebrity · Celebrity SummitRepositioning
Caribbean 9 nights Oct 20 – Oct 29, 2027 from Boston, Massachusetts to San Juan, Puerto Rico
Boston, Massachusetts · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Boston, Massachusetts · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Private Luxury Boston TourThe full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $806
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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 7 – Nov 14, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Roseau, Dominica · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Roseau, Dominica · 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 WallsBoiling Lake HikeSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $619
Book This Cruise@ Cruisebound
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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Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Roseau, Dominica · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Roseau, Dominica · 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 WallsBoiling Lake HikeSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $697
Book This Cruise@ Cruisebound
Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Nov 28 – Dec 5, 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 · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Castries, St. Lucia · St. Georges, Grenada, West Indies · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater HikePrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $642
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Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Roseau, Dominica · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Roseau, Dominica · 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 WallsBoiling Lake HikeSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $626
Book This Cruise@ Cruisebound
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 ApexRound-trip
Caribbean 10 nights Dec 18 – Dec 28, 2027 from Orlando, Florida
Orlando, Florida · Philipsburg, St. Maarten · … · Orlando, Florida7 ports
Orlando, Florida · Philipsburg, St. Maarten · Castries, St. Lucia · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Grand Turk, Turks and Caicos · Orlando, Florida
★ Bucket-list Random Wind 'Paradise Day Sail'Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachPrivate Full-Day Boat Charter +1 more
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from $2,167
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Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Dec 19 – Dec 26, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Roseau, Dominica · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Roseau, Dominica · 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 WallsBoiling Lake HikeSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $839
Book This Cruise@ Cruisebound
Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Dec 26 – Jan 2, 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 · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $839
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