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.

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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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Showing 19 of 19 sailings
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 9 – Nov 21, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $1,127
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Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 29 – Dec 11, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $945
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 11 – Dec 23, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $887
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 23 – Jan 4, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $1,860
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Jan 4 – Jan 16, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
View →
from $1,157
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Feb 1 – Feb 13, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac… +3 more
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from $1,305
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Mar 1 – Mar 13, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $1,379
Book This Cruise@ Cruisebound
Norwegian · Norwegian PrimaOne-way
Caribbean 10 nights Nov 3 – Nov 13, 2027 from New York, New York to San Juan, Puerto Rico
New York, New York · Royal Naval Dockyard, Bermuda · … · San Juan, Puerto Rico9 ports
New York, New York · Royal Naval Dockyard, Bermuda · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. John's, Antigua · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of BermudaJost Van DykeMt. Liamuiga Volcano Crater Hike +5 more
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from $1,554
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 8 – Nov 20, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
View →
from $1,140
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 28 – Dec 10, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail' +3 more
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from $1,155
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 10 – Dec 22, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsJost Van Dyke +3 more
View →
from $1,174
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 22 – Jan 3, 2028 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsJost Van Dyke +3 more
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from $1,702
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Jan 3 – Jan 15, 2028 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail' +3 more
View →
from $1,100
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 11 nights Jan 15 – Jan 26, 2028 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York7 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +2 more
View →
from $1,053
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Jan 26 – Feb 7, 2028 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsJost Van Dyke +3 more
View →
from $1,115
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Feb 7 – Feb 19, 2028 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsJost Van Dyke +3 more
View →
from $1,241
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Mar 6 – Mar 18, 2028 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsJost Van Dyke +3 more
View →
from $1,679
Book This Cruise@ Cruisebound
Norwegian · Norwegian PrimaRepositioning
Caribbean 7 nights Apr 22 – Apr 29, 2028 from San Juan, Puerto Rico to New York, New York
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikePrivate Catamaran Sail & Snorkel at Honeymoon Beac… +1 more
View →
from $990
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