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 · 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
Reset
Filtering Caribbean ×Princess ×Azamara × Clear all
Showing 36 of 85 sailings
Azamara · Azamara JourneyOne-way
Bermuda 9 nights Oct 29 – Nov 7, 2026 from New York, New York to San Juan, Puerto Rico
New York, New York · Hamilton, Bermuda · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Manhattan Helicopter TourRandom Wind 'Paradise Day Sail'Norman IslandWalk El Morro & Old San Juan's City Walls
View →
from $1,609
Book This Cruise@ Cruisebound
Azamara · Azamara JourneyOne-way
Caribbean 7 nights Nov 7 – Nov 14, 2026 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Half-Day Island Adventure & Trunk Bay BeachGrenada Private Taxi TourSwim with wild green sea turtles + two shipwrecks…
View →
from $2,059
Book This Cruise@ Cruisebound
Azamara · Azamara JourneyRound-trip
Caribbean 14 nights Nov 14 – Nov 28, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados15 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 · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +5 more
View →
from $4,856
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 +2 more
View →
from $1,645
Book This Cruise@ Cruisebound
Princess · Crown PrincessOne-way
Caribbean 8 nights Dec 19 – Dec 27, 2026 from Fort Lauderdale (Port Everglades), Florida to San Juan, Puerto Rico
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Antigua, Antigua & Barbuda · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowArubaPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City Walls
View →
from $515
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 BeachSwim with wild green sea turtles + two shipwrecks… +2 more
View →
from $1,914
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 +6 more
View →
from $7,329
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 HikeGrenada Private Taxi Tour +1 more
View →
from $474
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
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 BeachSwim with wild green sea turtles + two shipwrecks…
View →
from $618
Book This Cruise@ Cruisebound
Azamara · Azamara JourneyOne-way
Caribbean 11 nights Jan 14 – Jan 25, 2027 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Saint John, New Brunswick · … · Bridgetown, Barbados10 ports
Miami, Florida · Saint John, New Brunswick · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
View →
from $3,116
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
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 TourSwim with wild green sea turtles + two shipwrecks…
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
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 BeachSwim with wild green sea turtles + two shipwrecks… +1 more
View →
from $1,142
Book This Cruise@ Cruisebound
Azamara · Azamara JourneyOne-way
Caribbean 23 nights Jan 25 – Feb 17, 2027 from Bridgetown, Barbados to Buenos Aires, Argentina
Bridgetown, Barbados · Scarborough, Tobago · … · Buenos Aires, Argentina13 ports
Bridgetown, Barbados · Scarborough, Tobago · Ile Royale, French Guiana · Belem, Brazil · Recife, Brazil · Bahia de Salvador, Brazil · Buzios, Brazil · Rio de Janeiro, Brazil · Paraty, Brazil · Ilhabela, Brazil · Santos (Sao Paulo), Brazil · Montevideo, Uruguay · Buenos Aires, Argentina
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Full-Day Rio HighlightsPrivate Superboat to Castelhanos & Hidden Atlantic…Private Santos Full-Day +2 more
View →
from $8,052
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…Grenada Private Taxi Tour
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…Grenada Private Taxi TourSwim with wild green sea turtles + two shipwrecks… +1 more
View →
from $1,195
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Feb 5 – Feb 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 · Dominica, 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
View →
from $961
Book This Cruise@ Cruisebound
Princess · Crown PrincessRound-trip
Caribbean 7 nights Feb 7 – Feb 14, 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 · 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…Maho BeachSwim with wild green sea turtles + two shipwrecks…
View →
from $636
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 +1 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 HikeGrenada Private Taxi Tour +1 more
View →
from $660
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
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 BeachSwim with wild green sea turtles + two shipwrecks… +1 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 BeachGrenada Private Taxi Tour
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 BeachGrenada Private Taxi TourSwim with wild green sea turtles + two shipwrecks… +1 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
View →
from $1,109
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 BeachSwim with wild green sea turtles + two shipwrecks… +2 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 +1 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 HikeGrenada Private Taxi Tour +2 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
View →
from $919
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 BeachSwim with wild green sea turtles + two shipwrecks…
View →
from $814
Book This Cruise@ Cruisebound
Princess · Crown PrincessOne-way
Caribbean 9 nights Mar 26 – Apr 4, 2027 from Bridgetown, Barbados to Fort Lauderdale (Port Everglades), Florida
Bridgetown, Barbados · San Juan, Puerto Rico · … · Fort Lauderdale (Port Everglades), Florida6 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsMaho BeachAruba +1 more
View →
from $1,024
Book This Cruise@ Cruisebound
Princess · Crown PrincessOne-way
Caribbean 7 nights Mar 28 – Apr 4, 2027 from San Juan, Puerto Rico to Fort Lauderdale (Port Everglades), Florida
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachArubaEverglades Airboat Skim + Gator Boys Live Show
View →
from $514
Book This Cruise@ Cruisebound
Azamara · Azamara QuestOne-way
Caribbean 17 nights Oct 28 – Nov 14, 2027 from New York, New York to Bridgetown, Barbados
New York, New York · Hamilton, Bermuda · … · Bridgetown, Barbados13 ports
New York, New York · Hamilton, Bermuda · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Manhattan Helicopter TourRandom Wind 'Paradise Day Sail'Norman IslandWalk El Morro & Old San Juan's City Walls +4 more
View →
from $5,583
Book This Cruise@ Cruisebound
Azamara · Azamara QuestRound-trip
Caribbean 15 nights Nov 6 – Nov 21, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico16 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · 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 Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay BeachGrenada Private Taxi Tour +6 more
View →
from $5,751
Book This Cruise@ Cruisebound
Load more 49 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