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 ×Oceania ×Visits Grenada × Clear all
Showing 36 of 45 sailings
Princess · Coral PrincessRound-trip
Caribbean 14 nights Oct 15 – Oct 29, 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. Georges, Grenada, West Indies · 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 HikeMount Pelée Volcano Hike +5 more
View →
from $1,489
Book This Cruise@ Cruisebound
Oceania · Oceania VistaRepositioning
Caribbean 14 nights Oct 28 – Nov 11, 2026 from New York, New York to Miami, Florida
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida10 ports
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Full-Day Boat CharterJost Van DykePrivate Half-Day Island Adventure & Trunk Bay Beach +6 more
View →
from $3,412
Book This Cruise@ Cruisebound
Oceania · Oceania VistaRound-trip
Caribbean 14 nights Nov 11 – Nov 25, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida10 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Falmouth, Jamaica · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue Hole & Secret FallsAruba +5 more
View →
from $3,605
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
Princess · Crown PrincessOne-way
Caribbean 5 nights Jan 3 – Jan 8, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · Bridgetown, Barbados6 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
★ 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 +2 more
View →
from $474
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 BeachMount Pelée Volcano Hike +2 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 BeachMount Pelée Volcano HikeGrenada Private Taxi Tour +2 more
View →
from $702
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 +5 more
View →
from $1,142
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Jan 29 – Feb 5, 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 · Guadeloupe, Caribbean · 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 WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…La Grande Soufrière +2 more
View →
from $889
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 14 nights Jan 31 – Feb 14, 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 · Guadeloupe, Caribbean · 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 · Dominica, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…La Grande SoufrièreBoiling Lake & Valley of Desolation +4 more
View →
from $1,195
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Feb 12 – Feb 19, 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 · 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 WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater Hike +2 more
View →
from $889
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Feb 14 – Feb 21, 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 · 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…Mt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +2 more
View →
from $660
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 +5 more
View →
from $1,212
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Feb 26 – Mar 5, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Martinique · 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 WallsMaho BeachMount Pelée Volcano Hike +2 more
View →
from $854
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 BeachMount Pelée Volcano HikeBoiling Lake & Valley of Desolation +5 more
View →
from $1,254
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 7 nights Mar 12 – Mar 19, 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 · 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 WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater Hike +2 more
View →
from $1,119
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 · 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 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 +2 more
View →
from $1,263
Book This Cruise@ Cruisebound
Oceania · Oceania SirenaRound-trip
Caribbean 12 nights Nov 28 – Dec 10, 2027 from Miami, Florida
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida9 ports
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +4 more
View →
from $3,399
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
Oceania · Oceania SonataRound-trip
Caribbean 13 nights Dec 6 – Dec 19, 2027 from Miami, Florida
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida10 ports
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +5 more
View →
from $6,399
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
Princess · Coral PrincessRound-trip
Caribbean 14 nights Dec 20 – Jan 3, 2028 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 $1,484
Book This Cruise@ Cruisebound
Oceania · Oceania SirenaRound-trip
Caribbean 14 nights Dec 22 – Jan 5, 2028 from Miami, Florida
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida11 ports
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Fort-de-France, Martinique · Roseau, Dominica · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +6 more
View →
from $4,399
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 +2 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 HikeBoiling Lake & Valley of Desolation +6 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 BeachAdventure Antigua +6 more
View →
from $1,466
Book This Cruise@ Cruisebound
Oceania · Oceania SonataOne-way
Mexico 44 nights Jan 6 – Feb 19, 2028 from Los Angeles, California to Miami, Florida
Los Angeles, California · Ensenada, Mexico · … · Miami, Florida29 ports
Los Angeles, California · Ensenada, Mexico · Cabo San Lucas, Mexico · Acapulco, Mexico · Puerto Quetzal, Guatemala · Puntarenas, Costa Rica · Kiel Canal, Germany · Cartagena, Colombia · Georgetown, Grand Cayman, Cayman Islands · Miami, Florida · Philipsburg, St. Maarten · Fort-de-France, Martinique · Castries, St. Lucia · St. Georges, Grenada, West Indies · Port of Oranjestad, Aruba, Caribbean · Miami, Florida · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Pointe-a-Pitre, Guadeloupe · Tortola, B.V.I. · Miami, Florida · Kiel Canal, Germany · Cozumel, Mexico · Roatan, Honduras · Harvest Caye, Belize · Costa Maya, Mexico · Kiel Canal, Germany · Miami, Florida
★ Bucket-list Warner Bros. Studio Tour HollywoodValle de Guadalupe wine countryEl Arco & Lover's BeachLa Quebrada Cliff Divers +20 more
View →
from $20,599
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 +2 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 HikeBoiling Lake & Valley of Desolation +2 more
View →
from $736
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 8 nights Jan 20 – Jan 28, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · St. Lucia, Caribbean · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · St. Lucia, Caribbean · 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
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Gros Piton Summit HikeWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac… +3 more
View →
from $1,171
Book This Cruise@ Cruisebound
Oceania · Oceania SonataRound-trip
Caribbean 11 nights Jan 22 – Feb 2, 2028 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida7 ports
Miami, Florida · Philipsburg, St. Maarten · Fort-de-France, Martinique · Castries, St. Lucia · St. Georges, Grenada, West Indies · Port of Oranjestad, Aruba, Caribbean · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Mount Pelée & Saint-PierreCosol Tours +2 more
View →
from $5,399
Book This Cruise@ Cruisebound
Princess · Emerald PrincessRound-trip
Caribbean 14 nights Jan 23 – Feb 6, 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 · 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 $1,443
Book This Cruise@ Cruisebound
Load more 9 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