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 Princess ×Regent ×Visits St. Lucia × Clear all
Showing 36 of 74 sailings
Princess · Majestic PrincessRepositioning
Caribbean 12 nights Nov 7 – Nov 19, 2026 from New York, New York to Fort Lauderdale (Port Everglades), Florida
New York, New York · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida7 ports
New York, New York · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Curacao, Caribbean · Port of Oranjestad, Aruba, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Manhattan Helicopter TourMaho BeachMt. Liamuiga Volcano Crater HikeGros Piton Summit Hike +3 more
View →
from $811
Book This Cruise@ Cruisebound
Princess · Majestic PrincessRepositioning
Caribbean 33 nights Nov 19 – Dec 22, 2026 from Fort Lauderdale (Port Everglades), Florida to San Antonio, Santiago, Chile
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · San Antonio, Santiago, Chile16 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · St. Lucia, Caribbean · Bridgetown, Barbados · Fortaleza, Brazil · Rio de Janeiro, Brazil · Montevideo, Uruguay · Buenos Aires, Argentina · Montevideo, Uruguay · Puerto Madryn, Argentina · Stanley, Falkland Islands · Ushuaia, Argentina · Cockburn And Beagle Channels · Punta Arenas, Chile · Puerto Montt, Chile · San Antonio, Santiago, Chile
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachGros Piton Summit HikeSwim with wild green sea turtles + two shipwrecks… +10 more
View →
from $2,966
Book This Cruise@ Cruisebound
Princess · Island PrincessRound-trip
Caribbean 12 nights Nov 30 – Dec 12, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · St. Lucia, Caribbean · Bridgetown, Barbados · Dominica, Caribbean · St. Maarten, Netherlands Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowArubaKlein Curaçao Private Day TripGros Piton Summit Hike +3 more
View →
from $1,098
Book This Cruise@ Cruisebound
Princess · Enchanted PrincessRound-trip
Caribbean 14 nights Dec 3 – Dec 17, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · Dominica, Caribbean · St. Lucia, Caribbean · Port of Spain, Trinidad · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachMt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +3 more
View →
from $1,503
Book This Cruise@ Cruisebound
Princess · Coral PrincessRound-trip
Caribbean 11 nights Dec 26 – Jan 6, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Thomas, U.S. Virgin Islands · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · Bridgetown, Barbados · St. Lucia, Caribbean · St. Maarten, Netherlands Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks… +2 more
View →
from $1,199
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 14 nights Dec 27 – Jan 10, 2027 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 · St. Thomas, U.S. Virgin Islands · 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 BeachAdventure Antigua +5 more
View →
from $1,914
Book This Cruise@ Cruisebound
Regent · Seven Seas MarinerOne-way
Caribbean 18 nights Jan 4 – Jan 22, 2027 from Miami, Florida to Rio de Janeiro, Brazil
Miami, Florida · Willis Island · … · Rio de Janeiro, Brazil17 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · Willis Island · Devils Island, French Guiana · Willis Island · Belem, Brazil · Willis Island · Recife, Brazil · Maceio, Brazil · Bahia de Salvador, Brazil · Willis Island · Buzios, Brazil · Rio de Janeiro, Brazil
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay Beach +3 more
View →
from $12,760
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 8 – Jan 15, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
View →
from $839
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 10 – Jan 17, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +2 more
View →
from $618
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 15 – Jan 22, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Martinique · St. Georges, Grenada, West Indies · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsMaho BeachGrenada Private Taxi Tour +1 more
View →
from $960
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 17 – Jan 24, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Martinique · St. Georges, Grenada, West Indies · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachGrenada Private Taxi TourGros Piton Summit Hike +1 more
View →
from $702
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 22 – Jan 29, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
View →
from $1,169
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 14 nights Jan 24 – Feb 7, 2027 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 · St. Thomas, U.S. Virgin Islands · Guadeloupe, Caribbean · 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 BeachAdventure Antigua +4 more
View →
from $1,142
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Feb 19 – Feb 26, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
View →
from $1,109
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 14 nights Feb 21 – Mar 7, 2027 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 · St. Maarten, Netherlands Antilles · Martinique · 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 BeachAdventure Antigua +4 more
View →
from $1,212
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 14 nights Feb 28 – Mar 14, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Martinique · 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 WallsMaho BeachBoiling Lake & Valley of DesolationGrenada Private Taxi Tour +4 more
View →
from $1,254
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Mar 5 – Mar 12, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
View →
from $1,109
Book This Cruise@ Cruisebound
Regent · Seven Seas PrestigeRound-trip
Caribbean 12 nights Mar 5 – Mar 17, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida11 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · Pointe-a-Pitre, Guadeloupe · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike +5 more
View →
from $11,099
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 14 nights Mar 7 – Mar 21, 2027 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 · St. Thomas, U.S. Virgin Islands · 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 BeachAdventure Antigua +5 more
View →
from $1,240
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 14 nights Mar 14 – Mar 28, 2027 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 · 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 WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +5 more
View →
from $1,886
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Mar 19 – Mar 26, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
View →
from $919
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
Princess · Crown PrincessRound-trip
Caribbean 7 nights Mar 21 – Mar 28, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +2 more
View →
from $814
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
Regent · Seven Seas PrestigeOne-way
Bermuda 14 nights Apr 9 – Apr 23, 2027 from Miami, Florida to New York, New York
Miami, Florida · Willis Island · … · New York, New York13 ports
Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Castries, St. Lucia · Gustavia, St. Barts · San Juan, Puerto Rico · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · New York, New York
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex… +6 more
View →
from $10,199
Book This Cruise@ Cruisebound
Princess · Island PrincessRound-trip
Caribbean 10 nights Nov 5 – Nov 15, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Amber Cove, Dominican Republic · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Antigua, Antigua & Barbuda · St. Maarten, Netherlands Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live Show27 Charcos of DamajaguaWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
View →
from $1,041
Book This Cruise@ Cruisebound
Princess · Regal PrincessRepositioning
Caribbean 14 nights Nov 6 – Nov 20, 2027 from New York, New York to Miami, Florida
New York, New York · St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
New York, New York · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeAdventure Antigua +5 more
View →
from $1,324
Book This Cruise@ Cruisebound
Princess · Island PrincessRound-trip
Caribbean 14 nights Nov 15 – Nov 29, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Lucia, Caribbean · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachMt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +5 more
View →
from $1,109
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +2 more
View →
from $796
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 HikeBoiling Lake & Valley of Desolation +6 more
View →
from $1,450
Book This Cruise@ Cruisebound
Princess · Island PrincessRound-trip
Caribbean 14 nights Nov 29 – Dec 13, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · Bridgetown, Barbados · St. Lucia, Caribbean · St. Georges, Grenada, West Indies · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachMt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +5 more
View →
from $1,221
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Dec 3 – Dec 10, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +2 more
View →
from $1,158
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +2 more
View →
from $779
Book This Cruise@ Cruisebound
Princess · Coral PrincessRound-trip
Caribbean 14 nights Dec 6 – Dec 20, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Lucia, Caribbean · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachMt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +5 more
View →
from $1,161
Book This Cruise@ Cruisebound
Regent · Seven Seas PrestigeRound-trip
Caribbean 11 nights Dec 7 – Dec 18, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay Beach +4 more
View →
from $7,649
Book This Cruise@ Cruisebound
Princess · Star PrincessRound-trip
Caribbean 10 nights Dec 12 – Dec 22, 2027 from Port Canaveral, Florida
Port Canaveral, Florida · San Juan, Puerto Rico · … · Port Canaveral, Florida7 ports
Port Canaveral, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Antigua, Antigua & Barbuda · St. Thomas, U.S. Virgin Islands · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeGros Piton Summit Hike +2 more
View →
from $799
Book This Cruise@ Cruisebound
Load more 38 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