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 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
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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 Visits Port of Charlestown ×Repositioning ×One-way × Clear all
Showing 13 of 13 sailings
MSC Cruises · MSC OperaRepositioning
Mediterranean 18 nights Oct 29 – Nov 16, 2026 from Civitavecchia (Rome), Italy to La Romana, Dominican Republic
Civitavecchia (Rome), Italy · Genoa, Italy · … · La Romana, Dominican Republic10 ports
Civitavecchia (Rome), Italy · Genoa, Italy · Livorno (Florence/Pisa), Italy · Marseille, France · Barcelona, Spain · Tangier, Morocco · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · La Romana, Dominican Republic
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DaySail straight to Portofino from the cruise dockClimb the Leaning Tower of PisaCalanques National Park Boat Cruise from the Old P… +6 more
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from $1,016
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MSC Cruises · MSC OperaRepositioning
Mediterranean 17 nights Oct 30 – Nov 16, 2026 from Genoa, Italy to La Romana, Dominican Republic
Genoa, Italy · Livorno (Florence/Pisa), Italy · … · La Romana, Dominican Republic9 ports
Genoa, Italy · Livorno (Florence/Pisa), Italy · Marseille, France · Barcelona, Spain · Tangier, Morocco · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · La Romana, Dominican Republic
★ Bucket-list Sail straight to Portofino from the cruise dockClimb the Leaning Tower of PisaCalanques National Park Boat Cruise from the Old P…Sagrada Familia +5 more
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from $1,246
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MSC Cruises · MSC OperaRepositioning
Mediterranean 19 nights Nov 1 – Nov 20, 2026 from Marseille, France to Fort-de-France, Martinique
Marseille, France · Barcelona, Spain · … · Fort-de-France, Martinique10 ports
Marseille, France · Barcelona, Spain · Tangier, Morocco · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · La Romana, Dominican Republic · Catalina Island, Dominican Republic · Bridgetown, Barbados · Fort-de-France, Martinique
★ Bucket-list Calanques National Park Boat Cruise from the Old P…Sagrada FamiliaTangier Kasbah, Medina & American Legation Private…Private Half-Day Island Adventure & Trunk Bay Beach +6 more
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from $1,554
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MSC Cruises · MSC OperaRepositioning
Mediterranean 14 nights Nov 2 – Nov 16, 2026 from Barcelona, Spain to La Romana, Dominican Republic
Barcelona, Spain · Tangier, Morocco · … · La Romana, Dominican Republic6 ports
Barcelona, Spain · Tangier, Morocco · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · La Romana, Dominican Republic
★ Bucket-list Sagrada FamiliaTangier Kasbah, Medina & American Legation Private…Private Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $961
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MSC Cruises · MSC World EuropaRepositioning
Caribbean 21 nights Nov 14 – Dec 5, 2026 from Genoa, Italy to Fort-de-France, Martinique
Genoa, Italy · Civitavecchia (Rome), Italy · … · Fort-de-France, Martinique13 ports
Genoa, Italy · Civitavecchia (Rome), Italy · La Spezia (Cinque Terre), Italy · Marseille, France · Barcelona, Spain · Puerto del Rosario, Spain · Santa Cruz de Tenerife, Canary Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Fort-de-France, Martinique
★ Bucket-list Sail straight to Portofino from the cruise dockVatican, Sistine Chapel & Colosseum in One DayPrivate Cinque Terre by Minivan & Ferryboat from L…Calanques National Park Boat Cruise from the Old P… +9 more
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from $1,223
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MSC Cruises · MSC World EuropaRepositioning
Mediterranean 20 nights Nov 15 – Dec 5, 2026 from Civitavecchia (Rome), Italy to Fort-de-France, Martinique
Civitavecchia (Rome), Italy · La Spezia (Cinque Terre), Italy · … · Fort-de-France, Martinique12 ports
Civitavecchia (Rome), Italy · La Spezia (Cinque Terre), Italy · Marseille, France · Barcelona, Spain · Puerto del Rosario, Spain · Santa Cruz de Tenerife, Canary Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Fort-de-France, Martinique
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayPrivate Cinque Terre by Minivan & Ferryboat from L…Calanques National Park Boat Cruise from the Old P…Sagrada Familia +8 more
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from $1,449
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MSC Cruises · MSC World EuropaRepositioning
Caribbean 19 nights Nov 17 – Dec 6, 2026 from Marseille, France to Pointe-a-Pitre, Guadeloupe
Marseille, France · Barcelona, Spain · … · Pointe-a-Pitre, Guadeloupe11 ports
Marseille, France · Barcelona, Spain · Puerto del Rosario, Spain · Santa Cruz de Tenerife, Canary Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Calanques National Park Boat Cruise from the Old P…Sagrada FamiliaFuerteventuraTeide National Park +7 more
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from $1,229
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MSC Cruises · MSC World EuropaRepositioning
Mediterranean 14 nights Nov 18 – Dec 2, 2026 from Barcelona, Spain to Bridgetown, Barbados
Barcelona, Spain · Puerto del Rosario, Spain · … · Bridgetown, Barbados7 ports
Barcelona, Spain · Puerto del Rosario, Spain · Santa Cruz de Tenerife, Canary Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados
★ Bucket-list Sagrada FamiliaFuerteventuraTeide National ParkRandom Wind 'Paradise Day Sail' +3 more
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from $881
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Azamara · Azamara JourneyOne-way
Caribbean 6 nights Dec 12 – Dec 18, 2026 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico7 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +3 more
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from $1,645
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Azamara · Azamara JourneyOne-way
Caribbean 17 nights Dec 28 – Jan 14, 2027 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida14 ports
Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Castries, St. Lucia · Port of Charlestown, Nevis, St. Kitts and Nevis · Frederikstad, St. Croix · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Cosol Tours +8 more
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from $7,329
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Azamara · Azamara JourneyOne-way
Caribbean 11 nights Jan 14 – Jan 25, 2027 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Saint John, New Brunswick · … · Bridgetown, Barbados10 ports
Miami, Florida · Saint John, New Brunswick · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Reversing Falls & Fundy Tidal BorePrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail' +5 more
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from $3,116
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Azamara · Azamara QuestOne-way
Caribbean 7 nights Nov 28 – Dec 5, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico8 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +4 more
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from $2,449
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Azamara · Azamara QuestOne-way
Caribbean 7 nights Dec 12 – Dec 19, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico8 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +4 more
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from $2,383
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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.

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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