Moment 01
Island variety
A new beach, culture, and cuisine each day, from Dutch St. Maarten to Mexican Cozumel.
The Caribbean.
Sun, sea & island culture
The Caribbean remains the world's most beloved cruising region, and for good reason. Warm water, white-sand beaches, and a different island culture in every port make it endlessly rewarding, whether you're traveling as a couple, a family, or a multi-generational group.
From the eastern islands of St. Thomas and St. Maarten to the western reaches of Cozumel and Grand Cayman, itineraries range from week-long classics to shorter escapes, many sailing from convenient Florida ports. The newest ships are destinations in themselves, while smaller luxury lines slip into quieter harbors the big ships can't reach.
Best of all, many Caribbean itineraries require no passport for U.S. travelers on closed-loop sailings, making this the easiest warm-weather getaway we plan.
- The region
- Eastern & Western Caribbean
- Classic sailing
- 7 nights
- Ship style
- Mega-ship or small luxury
- Gateway
- Miami / San Juan
What you'll remember
Moments along the way.
Moment 02
Easy from home
Convenient departures from Florida ports, with closed-loop sailings that need no passport.
Moment 03
Family or couple
Resort-style mega-ships for the whole family, or intimate small ships for two.
Moment 04
Beneath the waves
Coral reefs and warm, clear water for snorkeling and diving straight off the beach.
Moment 05
Rum and rhythm
Steel drums, reggae and a rum punch at sunset, the easy pulse of the islands.
Moment 06
Old San Juan
Cobbled blue streets and colonial forts in the most storied port in the Caribbean.
The route
A sample sailing.
6 stops · Miami to St. Kitts
Tap a stop to jump to that day · drag to explore
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1 Day 1Miami, Florida
Embark in the cruise capital of the world and sail south into the warm blue of the Caribbean.
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2 Day 2Grand Turk
Powder-soft sand and one of the region's great reefs, steps from where the ship ties up.
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3 Day 3San Juan, Puerto Rico
The cobbled lanes and colonial forts of Old San Juan, painted in tropical color.
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4 Day 4St. Thomas, USVI
Beautiful Magens Bay, duty-free Charlotte Amalie, and easy island-hopping to St. John.
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5 Day 5St. Maarten
A two-nation island of Dutch buzz and French flair, with a beach for every mood.
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6 Days 6-7St. Kitts & at sea
Rainforest and the hilltop fortress of Brimstone Hill, then a relaxed day at sea back to Miami.
Every sailing we book is tailored: this is a starting point, not a package.
When to go
The best time to sail.
The Caribbean sails all year, but the calendar splits cleanly: a dry, settled winter-into-spring peak, and a summer-into-fall stretch when fares fall and we keep one eye on the hurricane maps. Here is how we read the year.
December–April
The dry, sunny peak season: warm days, calm seas and the liveliest ports.
May & November
Shoulder months with warm weather, thinner crowds and better value.
June–November
Hurricane season brings the lowest fares and some weather risk; August through October are the watch months and itineraries stay flexible.
Good to know
The Caribbean cruise questions.
How long is a Caribbean cruise?+
Sailings range from 3 to 4 night escapes to week-long classics and longer, many round trip from Florida ports.
Do I need a passport?+
Many closed-loop sailings from U.S. ports allow travel with a birth certificate and photo ID, though we always recommend a passport. We confirm the requirements for your sailing.
When is the best time to cruise the Caribbean?+
December through April is the dry, sunny peak. Summer and fall are warm and less crowded but fall within hurricane season.
Eastern or Western Caribbean?+
Eastern itineraries favor beaches and duty-free shopping; Western routes reach Mexico, Central America and Mayan sites. We match the route to what you want.
From the journal
Reading on The Caribbean.
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Ready for
The Caribbean?
We'll handle the ship, the itinerary, and every detail in between.
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