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 · 2 selected
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 Royal Caribbean ×Seabourn ×Visits Port of Basseterre × Clear all
Showing 36 of 133 sailings
Royal Caribbean · Star of the SeasRound-trip
Bahamas 7 nights Jun 14 – Jun 21, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $1,584
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Jun 20 – Jun 27, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
View →
from $1,223
Book This Cruise@ Cruisebound
Royal Caribbean · Allure of the SeasRound-trip
Caribbean 8 nights Jun 27 – Jul 5, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · San Juan, Puerto Rico · Perfect Day at CocoCay · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
View →
from $1,136
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Jul 4 – Jul 11, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
View →
from $1,294
Book This Cruise@ Cruisebound
Royal Caribbean · Star of the SeasRound-trip
Bahamas 7 nights Jul 5 – Jul 12, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $1,108
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Jul 18 – Jul 25, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
View →
from $1,416
Book This Cruise@ Cruisebound
Royal Caribbean · Allure of the SeasRound-trip
Bahamas 8 nights Jul 25 – Aug 2, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'Private Full-Day Boat Charter +1 more
View →
from $1,125
Book This Cruise@ Cruisebound
Royal Caribbean · Star of the SeasRound-trip
Caribbean 7 nights Jul 26 – Aug 2, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $1,162
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Aug 1 – Aug 8, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeRandom Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +2 more
View →
from $849
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Aug 15 – Aug 22, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
View →
from $694
Book This Cruise@ Cruisebound
Royal Caribbean · Star of the SeasRound-trip
Caribbean 7 nights Aug 16 – Aug 23, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $887
Book This Cruise@ Cruisebound
Royal Caribbean · Allure of the SeasRound-trip
Bahamas 8 nights Aug 22 – Aug 30, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · San Juan, Puerto Rico · Perfect Day at CocoCay · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
View →
from $654
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Aug 29 – Sep 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
View →
from $640
Book This Cruise@ Cruisebound
Royal Caribbean · Star of the SeasRound-trip
Bahamas 7 nights Sep 6 – Sep 13, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $1,138
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Sep 12 – Sep 19, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
View →
from $716
Book This Cruise@ Cruisebound
Royal Caribbean · Allure of the SeasRound-trip
Bahamas 8 nights Sep 19 – Sep 27, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · San Juan, Puerto Rico · Perfect Day at CocoCay · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
View →
from $586
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Sep 26 – Oct 3, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
View →
from $687
Book This Cruise@ Cruisebound
Royal Caribbean · Star of the SeasRound-trip
Caribbean 7 nights Sep 27 – Oct 4, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $1,078
Book This Cruise@ Cruisebound
Seabourn · Seabourn VentureRepositioning
Caribbean 24 nights Oct 5 – Oct 29, 2026 from Halifax, Nova Scotia to Rio de Janeiro, Brazil
Halifax, Nova Scotia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Rio de Janeiro, Brazil14 ports
Halifax, Nova Scotia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Rodney Bay, St. Lucia · Bridgetown, Barbados · Port of Spain, Trinidad · Devils Island, French Guiana · Crossing The Equator · Fortaleza, Brazil · Natal(Rio Grande do Norte), Brazil · Bahia de Salvador, Brazil · Buzios, Brazil · Paraty, Brazil · Rio de Janeiro, Brazil
★ Bucket-list Peggy's Cove & LunenburgMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks…Private Full-Day Rio Highlights
View →
from $12,798
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 10 – Oct 17, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
View →
from $573
Book This Cruise@ Cruisebound
Royal Caribbean · Star of the SeasRound-trip
Caribbean 7 nights Oct 18 – Oct 25, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $720
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 24 – Oct 31, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
View →
from $580
Book This Cruise@ Cruisebound
Royal Caribbean · Allure of the SeasRound-trip
Bahamas 7 nights Nov 1 – Nov 8, 2026 from Miami, Florida
Miami, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Daredevil's PeakWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike
View →
from $705
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 1 – Nov 8, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
View →
from $573
Book This Cruise@ Cruisebound
Royal Caribbean · Adventure of the SeasRound-trip
Caribbean 8 nights Nov 7 – Nov 15, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · San Juan, Puerto Rico · Grand Turk, Turks and Caicos · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
View →
from $744
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Nov 14 – Nov 21, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay BeachBoiling Lake Hike +2 more
View →
from $576
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 15 – Nov 22, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
View →
from $552
Book This Cruise@ Cruisebound
Royal Caribbean · Explorer of the SeasRound-trip
Caribbean 9 nights Nov 18 – Nov 27, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. John's, Antigua · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · St. John's, Antigua · Bridgetown, Barbados · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Half-Day Island Adventure & Trunk Bay BeachSwim with wild green sea turtles + two shipwrecks…Boiling Lake Hike +1 more
View →
from $739
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 8 nights Nov 20 – Nov 28, 2026 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Miami, Florida · San Juan, Puerto Rico · Great Harbor, Peter Island, BVI · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Port Elizabeth, Saint Vincent · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
View →
from $4,098
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 22 – Nov 29, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
View →
from $542
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Nov 22 – Dec 6, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida11 ports
Miami, Florida · San Juan, Puerto Rico · Road Bay, Anguilla · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Terre-de-haut, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Virgin Gorda, British Virgin Islands · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +1 more
View →
from $7,753
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Nov 28 – Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
View →
from $530
Book This Cruise@ Cruisebound
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 HikeRandom Wind 'Paradise Day Sail'
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
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
View →
from $597
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Dec 6 – Dec 20, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida11 ports
Miami, Florida · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Terre-de-haut, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Road Bay, Anguilla · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +1 more
View →
from $5,498
Book This Cruise@ Cruisebound
Load more 97 more

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