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 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 From San Juan, Puerto Rico ×Repositioning ×One-way × Clear all
Showing 18 of 18 sailings
Azamara · Azamara JourneyOne-way
Caribbean 7 nights Nov 7 – Nov 14, 2026 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachÎle aux Marins +4 more
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from $2,059
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Princess · Crown PrincessOne-way
Caribbean 5 nights Jan 3 – Jan 8, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · Bridgetown, Barbados6 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +2 more
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from $474
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Oceania · Oceania AlluraOne-way
Caribbean 8 nights Feb 19 – Feb 27, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Gustavia, St. Barts · … · Miami, Florida7 ports
San Juan, Puerto Rico · Gustavia, St. Barts · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Open-Top Mini Moke Island Tour of St. BartsRandom Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +3 more
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from $2,970
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Royal Caribbean · Rhapsody of the SeasOne-way
Caribbean 10 nights Mar 6 – Mar 16, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Tortola, B.V.I. · … · Miami, Florida9 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Croix, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +5 more
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from $729
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Viking Ocean · Viking SeaRepositioning
Mediterranean 13 nights Mar 6 – Mar 19, 2027 from San Juan, Puerto Rico to Barcelona, Spain
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · Barcelona, Spain9 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · Sail the Atlantic Ocean · Funchal, Madeira, Portugal · Sail the Atlantic Ocean · Cadiz (Seville), Spain · Sail the Alboran Sea · Valencia, Spain · Barcelona, Spain
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'ARC Transatlantic RallyPico do Arieiro to Pico Ruivo +4 more
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from $3,499
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Princess · Crown PrincessOne-way
Caribbean 7 nights Mar 28 – Apr 4, 2027 from San Juan, Puerto Rico to Fort Lauderdale (Port Everglades), Florida
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachArubaKlein Curaçao Private Day Trip +1 more
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from $514
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Regent · Seven Seas PrestigeOne-way
Bahamas 10 nights Mar 30 – Apr 9, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Tortola, B.V.I. · … · Miami, Florida11 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · La Romana, Dominican Republic · Willis Island · Nassau, Bahamas · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikePrivate Half-Day Island Adventure & Trunk Bay Beach +7 more
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from $6,049
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Celebrity · Celebrity ConstellationRepositioning
Caribbean 13 nights Apr 3 – Apr 16, 2027 from San Juan, Puerto Rico to Barcelona, Spain
San Juan, Puerto Rico · Philipsburg, St. Maarten · Tangier, Morocco · Malaga, Spain · Barcelona, Spain
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Tangier Kasbah, Medina & American Legation Private…Granada & the Alhambra +1 more
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from $501
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Norwegian · Norwegian PrimaRepositioning
Mediterranean 17 nights Apr 4 – Apr 21, 2027 from San Juan, Puerto Rico to Civitavecchia (Rome), Italy
San Juan, Puerto Rico · Ponta Delgada, Azores, Portugal · … · Civitavecchia (Rome), Italy11 ports
San Juan, Puerto Rico · Ponta Delgada, Azores, Portugal · Funchal, Madeira, Portugal · Melilla, Morocco · Motril, Spain · Ibiza, Spain · Palma de Mallorca, Spain · Barcelona, Spain · Villefranche, France · Livorno (Florence/Pisa), Italy · Civitavecchia (Rome), Italy
★ Bucket-list Walk El Morro & Old San Juan's City WallsSete Cidades Twin LakesPico do Arieiro to Pico RuivoMelilla la Vieja +7 more
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from $2,919
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Royal Caribbean · Vision of the SeasOne-way
Caribbean 10 nights Apr 4 – Apr 14, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +5 more
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from $792
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Virgin Voyages · Valiant LadyOne-way
Bahamas Apr 10, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Grand Turk, Turks and Caicos · Bimini, Bahamas · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsGibbs Cay Private Stingray Swim & Reef SnorkelSwim with Wild Dolphins at Honeymoon HarbourStar Island & Millionaire's Row Skyline Cruise on…
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from $922
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Disney · Disney DreamOne-way
Bahamas 4 nights Apr 23 – Apr 27, 2027 from San Juan, Puerto Rico to Port Canaveral, Florida
San Juan, Puerto Rico · Disney Lookout Cay · Castaway Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Historical & Cultural SUV Tour of EleutheraAbaco Backcountry Fishing AdventureKennedy Space Center Visitor Complex
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from $1,509
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Royal Caribbean · Grandeur of the SeasOne-way
Panama Canal 7 nights Nov 27 – Dec 4, 2027 from San Juan, Puerto Rico to Colon, Panama
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Colon, Panama6 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Willemstad, Curacao · Colon, Panama
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Cosol Tours +2 more
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from $597
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Azamara · Azamara QuestOne-way
Northern Europe 8 nights Dec 19 – Dec 27, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Portsmouth, England · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachStonehenge & Salisbury Cathedral +4 more
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from $3,086
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Celebrity · Celebrity SummitOne-way
Caribbean 4 nights Jan 2 – Jan 6, 2028 from San Juan, Puerto Rico to Fort Lauderdale (Port Everglades), Florida
San Juan, Puerto Rico · Philipsburg, St. Maarten · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Everglades Airboat Skim + Gator Boys Live Show
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from $506
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Viking Ocean · Viking SkyRepositioning
Mediterranean 11 nights Feb 27 – Mar 9, 2028 from San Juan, Puerto Rico to Lisbon, Portugal
San Juan, Puerto Rico · Sail the Atlantic Ocean · … · Lisbon, Portugal8 ports
San Juan, Puerto Rico · Sail the Atlantic Ocean · Sail the North Atlantic Ocean · Las Palmas, Gran Canaria, Canary Islands · Santa Cruz de Tenerife, Canary Islands · Funchal, Madeira, Portugal · Sail the North Atlantic Ocean · Lisbon, Portugal
★ Bucket-list Walk El Morro & Old San Juan's City WallsARC Transatlantic RallyTransatlantic Sailing VoyageRoque Nublo & Tejeda +3 more
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from $3,099
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Princess · Emerald PrincessOne-way
Caribbean 7 nights Mar 26 – Apr 2, 2028 from San Juan, Puerto Rico to Fort Lauderdale (Port Everglades), Florida
San Juan, Puerto Rico · Curacao, Caribbean · Port of Oranjestad, Aruba, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsKlein Curaçao Private Day TripArubaKlein Bonaire +1 more
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from $634
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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
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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