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 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
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
Must visit a specific port clear
Reset
Filtering Caribbean ×Visits St. Lucia ×One-way × Clear all
Showing 23 of 23 sailings
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Nov 28 – Dec 5, 2026 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Virgin Gorda, British Virgin Islands · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater HikeThe Baths National Park +1 more
View →
from $4,098
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 14 nights Dec 5 – Dec 19, 2026 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados13 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Saint-Pierre, Newfoundland, Canada · Roseau, Dominica · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +2 more
View →
from $6,798
Book This Cruise@ Cruisebound
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
View →
from $1,645
Book This Cruise@ Cruisebound
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
View →
from $7,329
Book This Cruise@ Cruisebound
Costa · Costa FascinosaOne-way
Caribbean 14 nights Jan 21 – Feb 4, 2027 from Pointe-a-Pitre, Guadeloupe to Pointe-a-Pitre, Guadeloupe
Guadalupa Bay · Pointe-a-Pitre, Guadeloupe · … · Pointe-a-Pitre, Guadeloupe16 ports
Guadalupa Bay · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Guadalupa Bay · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic · Catalina Island, Dominican Republic · Samana, Dominican Republic · Puerto Plata, Dominican Republic · Grand Turk, Turks and Caicos · Cabo Rojo, Dominican Republic · La Romana, Dominican Republic · 15.9 N, 63.1 W,caribbean Sea · Castries, St. Lucia · Bridgetown, Barbados · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Death in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeNorman IslandSaona Island Private Speedboat & Natural Pool Day +5 more
View →
from $1,961
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Feb 27 – Mar 6, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +1 more
View →
from $4,798
Book This Cruise@ Cruisebound
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
View →
from $729
Book This Cruise@ Cruisebound
Regent · Seven Seas PrestigeOne-way
Caribbean 10 nights Mar 20 – Mar 30, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Willis Island · … · San Juan, Puerto Rico10 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Roseau, Dominica · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterBoiling Lake Hike +6 more
View →
from $6,099
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurOne-way
Mediterranean 14 nights Mar 31 – Apr 14, 2027 from Panama City, Panama to Miami, Florida
Panama City, Panama · Kiel Canal, Germany · … · Miami, Florida14 ports
Panama City, Panama · Kiel Canal, Germany · Cartagena, Spain · Santa Marta, Colombia · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · St. Georges, Grenada, West Indies · Castries, St. Lucia · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list The Roman Theatre of Cartagena with the Rafael Mon…The Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +5 more
View →
from $8,699
Book This Cruise@ Cruisebound
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
View →
from $792
Book This Cruise@ Cruisebound
Royal Caribbean · Grandeur of the SeasOne-way
Caribbean 7 nights Apr 24 – May 1, 2027 from Colon, Panama to San Juan, Puerto Rico
Colon, Panama · Port of Kingstown, St. Vincent & the Grenadines · … · San Juan, Puerto Rico6 ports
Colon, Panama · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Panama Canal Full TransitLa Soufrière Volcano Summit HikeCosol ToursPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
View →
from $539
Book This Cruise@ Cruisebound
Seabourn · Seabourn VentureOne-way
Caribbean 8 nights Oct 1 – Oct 9, 2027 from Halifax, Nova Scotia to Bridgetown, Barbados
Halifax, Nova Scotia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Peggy's Cove & LunenburgMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks…
View →
from $5,998
Book This Cruise@ Cruisebound
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
View →
from $597
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Nov 27 – Dec 4, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +1 more
View →
from $4,498
Book This Cruise@ Cruisebound
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
View →
from $2,449
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 17 nights Dec 11 – Dec 28, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Philipsburg, St. Maarten15 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Scarborough, Tobago · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port Elizabeth, Saint Vincent · Saint-Pierre, Newfoundland, Canada · Terre-de-haut, Guadeloupe · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Road Bay, Anguilla · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Full-Day Curaçao Island Tour with Local Ex…Klein BonaireGrenada Private Taxi Tour +4 more
View →
from $8,998
Book This Cruise@ Cruisebound
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
View →
from $2,383
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurOne-way
Caribbean 10 nights Jan 5 – Jan 15, 2028 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Willis Island · … · Bridgetown, Barbados10 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Gustavia, St. Barts · Philipsburg, St. Maarten · Pointe-a-Pitre, Guadeloupe · Roseau, Dominica · Fort-de-France, Martinique · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandJost Van DykeRandom Wind 'Paradise Day Sail' +5 more
View →
from $6,399
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 14 nights Jan 8 – Jan 22, 2028 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Philipsburg, St. Maarten12 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Full-Day Curaçao Island Tour with Local Ex…ArubaKlein Bonaire +4 more
View →
from $8,898
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 29 – Feb 5, 2028 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +1 more
View →
from $4,798
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurOne-way
Caribbean 9 nights Feb 24 – Mar 4, 2028 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Castries, St. Lucia · … · Miami, Florida9 ports
Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Roseau, Dominica · Pointe-a-Pitre, Guadeloupe · Gustavia, St. Barts · Philipsburg, St. Maarten · Willis Island · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursMount Pelée & Saint-PierreBoiling Lake Hike +4 more
View →
from $5,899
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Mar 11 – Mar 18, 2028 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'
View →
from $4,798
Book This Cruise@ Cruisebound
Azamara · Azamara QuestOne-way
Caribbean 9 nights Mar 13 – Mar 22, 2028 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Miami, Florida8 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Castries, St. Lucia · Saint- Pierre · Roseau, Dominica · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourCosol ToursBoiling Lake Hike +3 more
View →
from $3,932
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