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
My result then click any cruise row to open it
Where to? tap as many as you like Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
Cruise level tap one or more Luxury Premium Contemporary River
+ pick specific cruise lines
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 Visits St. Thomas ×Repositioning × Clear all
Showing 12 of 12 sailings
Oceania · Oceania VistaRepositioning
Caribbean 14 nights Oct 28 – Nov 11, 2026 from New York, New York to Miami, Florida
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida10 ports
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Full-Day Boat CharterJost Van DykePrivate Half-Day Island Adventure & Trunk Bay Beach +6 more
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from $3,412
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Norwegian · Norwegian EpicRepositioning
Bahamas 14 nights Nov 1 – Nov 15, 2026 from Barcelona, Spain to Port Canaveral, Florida
Barcelona, Spain · Cadiz (Seville), Spain · … · Port Canaveral, Florida6 ports
Barcelona, Spain · Cadiz (Seville), Spain · Santa Cruz de Tenerife, Canary Islands · St. Thomas, U.S. Virgin Islands · Great Stirrup Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Sagrada FamiliaReal Alcázar de SevillaTeide National ParkPrivate Catamaran Sail & Snorkel at Honeymoon Beac… +2 more
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from $818
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Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Nov 8 – Nov 22, 2026 from Boston, Massachusetts to New Orleans, Louisiana
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · … · New Orleans, Louisiana8 ports
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · St. Lucia, Caribbean · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Georgetown, Grand Cayman, Cayman Islands · New Orleans, Louisiana
★ Bucket-list Private Luxury Boston TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Grenada Private Taxi TourPrivate Full-Day Curaçao Island Tour with Local Ex… +3 more
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from $970
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Oceania · Oceania InsigniaRepositioning
Caribbean 54 nights Feb 14 – Apr 9, 2027 from Valparaiso (Santiago), Chile to Miami, Florida
Valparaiso (Santiago), Chile · Puerto Montt, Chile · … · Miami, Florida33 ports
Valparaiso (Santiago), Chile · Puerto Montt, Chile · Castro, Chile · Puerto Chacabuco, Chile · Laguna San Raphael, Chile · Kiel Canal, Germany · Punta Arenas, Chile · Ushuaia, Argentina · Kiel Canal, Germany · Port Stanley, Falkland Islands · Puerto Madryn, Argentina · Buenos Aires, Argentina · Montevideo, Uruguay · Punta del Este, Uruguay · Rio Grande, Rio Grande do Sul, Brazil · Florianopolis, Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil · Paraty, Brazil · Ilha Grande, Brazil · Buzios, Brazil · Rio de Janeiro, Brazil · Kiel Canal, Germany · Alter do Chao, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Santarem, Brazil · Kiel Canal, Germany · Bridgetown, Barbados · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…Isla MartilloPrivate Full-Day Península Valdés +8 more
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from $16,399
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Oceania · Oceania InsigniaRepositioning
Caribbean 21 nights Mar 19 – Apr 9, 2027 from Rio de Janeiro, Brazil to Miami, Florida
Rio de Janeiro, Brazil · Kiel Canal, Germany · … · Miami, Florida12 ports
Rio de Janeiro, Brazil · Kiel Canal, Germany · Alter do Chao, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Santarem, Brazil · Kiel Canal, Germany · Bridgetown, Barbados · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Private Full-Day Rio HighlightsSwim with wild green sea turtles + two shipwrecks…Private Half-Day Island Adventure & Trunk Bay BeachPrivate Full-Day Boat Charter +1 more
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from $6,299
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Carnival · Carnival FirenzeRepositioning
Caribbean May 16, 2027 from Miami, Florida to New York, New York
Miami, Florida · Celebration Key, Bahamas · … · New York, New York6 ports
Miami, Florida · Celebration Key, Bahamas · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Kayak the Lucayan Caves & Gold Rock Beach with the…ArubaPrivate Catamaran Sail & Snorkel at Honeymoon Beac… +1 more
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from $547
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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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Cunard · Queen ElizabethRepositioning
Caribbean 27 nights Oct 29 – Nov 25, 2027 from Barcelona, Spain to Miami, Florida
Barcelona, Spain · Seville, Spain · … · Miami, Florida13 ports
Barcelona, Spain · Seville, Spain · Lanzarote, Canary Islands, Spain · Santa Cruz de Tenerife, Canary Islands · Miami, Florida · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Grenada, Caribbean · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Sagrada FamiliaTeide National ParkStar Island & Millionaire's Row Skyline Cruise on…Private Catamaran Sail & Snorkel at Honeymoon Beac… +4 more
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from $3,369
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Carnival · Carnival FirenzeRepositioning
Caribbean Nov 2, 2027 from New York, New York to Port Canaveral, Florida
New York, New York · St. Thomas, U.S. Virgin Islands · … · Port Canaveral, Florida7 ports
New York, New York · St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Grand Turk, Turks and Caicos · Port Canaveral, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Buck Island ReefAruba +2 more
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from $696
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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 HikeSwim with wild green sea turtles + two shipwrecks… +3 more
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from $1,324
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Azamara · Azamara OnwardRepositioning
Mediterranean 13 nights Dec 9 – Dec 22, 2027 from Malaga, Spain to Miami, Florida
Malaga, Spain · Tangier, Morocco · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Granada & the AlhambraTangier Kasbah, Medina & American Legation Private…Private Full-Day Boat CharterStar Island & Millionaire's Row Skyline Cruise on…
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from $2,554
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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
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from $990
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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.

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