Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

When are you free? — only cruises that fit entirely inside your dates
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Where to? tap as many as you like 1 selected · clear Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
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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 Bermuda ×Norwegian ×Visits St. Lucia × Clear all
Showing 6 of 6 sailings
Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Nov 27 – Dec 8, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. John's, Antigua · St. Lucia, Caribbean · Philipsburg, St. Maarten · Philadelphia, Pennsylvania
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Half-Day Island Adventure & Trunk Bay BeachGros Piton Summit Hike +1 more
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from $927
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Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Dec 23 – Jan 3, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Mt. Liamuiga Volcano Crater HikeGros Piton Summit HikePrivate Half-Day Island Adventure & Trunk Bay BeachWalk El Morro & Old San Juan's City Walls +1 more
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from $1,516
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Norwegian · Norwegian PearlRound-trip
Caribbean 12 nights Jan 3 – Jan 15, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania8 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · Bridgetown, Barbados · St. Lucia, Caribbean · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Random Wind 'Paradise Day Sail'Swim with wild green sea turtles + two shipwrecks…Gros Piton Summit HikePrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $885
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 12 nights Jan 15 – Jan 27, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania8 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · St. Lucia, Caribbean · Bridgetown, Barbados · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Random Wind 'Paradise Day Sail'Gros Piton Summit HikeSwim with wild green sea turtles + two shipwrecks…Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $885
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Jan 27 – Feb 7, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · St. John's, Antigua · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · St. John's, Antigua · St. Lucia, Caribbean · Philipsburg, St. Maarten · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Private Half-Day Island Adventure & Trunk Bay BeachGros Piton Summit HikeRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
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from $831
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Feb 7 – Feb 18, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · St. Lucia, Caribbean · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Random Wind 'Paradise Day Sail'Gros Piton Summit HikePrivate Half-Day Island Adventure & Trunk Bay BeachWalk El Morro & Old San Juan's City Walls +1 more
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from $831
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.

19 lines
aboard
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