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 · 1 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 Princess ×Visits Tortola × Clear all
Showing 22 of 22 sailings
Princess · Regal PrincessRound-trip
Mexico 15 nights Nov 20 – Dec 5, 2027 from Miami, Florida
Miami, Florida · Belize City, Belize · … · Miami, Florida11 ports
Miami, Florida · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Celebration Key, Bahamas · Miami, Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Great Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…El Cielo + Palancar + Columbia 3-Stop Snorkel +5 more
View →
from $1,418
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Nov 26 – Dec 3, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater Hike +1 more
View →
from $1,263
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Bahamas 15 nights Nov 27 – Dec 12, 2027 from Miami, Florida
Miami, Florida · Amber Cove, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Tortola, B.V.I. · Miami, Florida · Princess Cays, Bahamas · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…27 Charcos of DamajaguaWalk El Morro & Old San Juan's City WallsMaho Beach +3 more
View →
from $1,513
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 14 nights Nov 28 – Dec 12, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeGrenada Private Taxi Tour +3 more
View →
from $1,450
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Dec 10 – Dec 17, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · Dominica, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater Hike
View →
from $1,167
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2027 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. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · Dominica, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks…
View →
from $586
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 14 nights Dec 19 – Jan 2, 2028 from Miami, Florida
Miami, Florida · Amber Cove, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Tortola, B.V.I. · Miami, Florida · Celebration Key, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…27 Charcos of DamajaguaWalk El Morro & Old San Juan's City WallsMaho Beach +3 more
View →
from $2,293
Book This Cruise@ Cruisebound
Princess · Star PrincessRound-trip
Caribbean 14 nights Dec 22 – Jan 5, 2028 from Port Canaveral, Florida
Port Canaveral, Florida · Celebration Key, Bahamas · … · Port Canaveral, Florida11 ports
Port Canaveral, Florida · Celebration Key, Bahamas · Tortola, B.V.I. · St. Maarten, Netherlands Antilles · Martinique · St. Lucia, Caribbean · Antigua, Antigua & Barbuda · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Grand Turk, Turks and Caicos · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexKayak the Lucayan Caves & Gold Rock Beach with the…Jost Van DykeMaho Beach +3 more
View →
from $1,494
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Dec 24 – Dec 31, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater Hike +1 more
View →
from $1,496
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 14 nights Dec 26 – Jan 9, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeGrenada Private Taxi Tour +3 more
View →
from $1,953
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 14 nights Jan 2 – Jan 16, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachSwim with wild green sea turtles + two shipwrecks… +3 more
View →
from $1,466
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Jan 7 – Jan 14, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater Hike +1 more
View →
from $1,326
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Jan 9 – Jan 16, 2028 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. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeGrenada Private Taxi Tour +1 more
View →
from $736
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Feb 4 – Feb 11, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater Hike +1 more
View →
from $1,718
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 14 nights Feb 6 – Feb 20, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeGrenada Private Taxi Tour +3 more
View →
from $1,511
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 14 nights Feb 13 – Feb 27, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachSwim with wild green sea turtles + two shipwrecks… +3 more
View →
from $1,818
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Feb 18 – Feb 25, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater Hike +1 more
View →
from $1,363
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 14 nights Feb 20 – Mar 5, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeGrenada Private Taxi Tour +3 more
View →
from $1,918
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Mar 3 – Mar 10, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater Hike +1 more
View →
from $1,868
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 14 nights Mar 5 – Mar 19, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeGrenada Private Taxi Tour +3 more
View →
from $1,653
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Mar 17 – Mar 24, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater Hike +1 more
View →
from $1,938
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Mar 19 – Mar 26, 2028 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. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeGrenada Private Taxi Tour +1 more
View →
from $841
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