Caribbean Cruises

The Caribbean is where cruising grew up, and it is still the easiest holiday on water: fly to Florida or San Juan, step aboard, and wake up somewhere new and turquoise almost every day. The trick is knowing which Caribbean you are booking — the region sails as three distinct routes, and they feel like three different vacations.

Eastern Caribbean — the classic first sailing

St. Thomas, St. Maarten and San Juan anchor the Eastern routes, with stops at private islands and the Dominican Republic filling out the week. The sailing distances are short, so you get long days in port and calm overnight hops. This is the beach Caribbean: Magens Bay's perfect curve on St. Thomas, duty-free shopping in Charlotte Amalie, French-meets-Dutch food on St. Maarten, and old San Juan's blue-cobblestone streets for the history hour. If your ideal day is sand, swim, rum punch, repeat — book Eastern. It is also the gentlest introduction for first-time cruisers.

Western Caribbean — reefs, ruins and rhythm

Western routes run from Florida and the Gulf ports to Cozumel, Grand Cayman, Jamaica and Belize — and they are built for people who do things. Snorkel Cozumel's Palancar Reef in the morning, climb a Mayan pyramid at Tulum or Chichén Itzá by afternoon. Swim with rays at Stingray City, zip-line over Jamaican jungle, river-tube through Belizean caves. Sea days run longer here, which suits the mega-ships: there is time to actually use the water slides, surf simulators and Broadway shows you paid for.

Southern Caribbean — the far islands

Sail from San Juan or Barbados for seven to fourteen nights and the map changes: Aruba's dry, windy beaches, Curaçao's pastel waterfront, Bonaire's shore-diving, Grenada's nutmeg hills and St. Lucia's Pitons rising straight out of the sea. Southern routes sit below the main hurricane belt, draw fewer families and more seasoned cruisers, and feel noticeably less crowded in port. They cost more and take longer — and for many repeat cruisers, they are the Caribbean at its best.

The Bahamas and the short cruise

Nassau and Freeport, three or four nights out of Florida, are the gateway drug of cruising: cheap, cheerful and close to home. Almost every line now pairs the Bahamas with its own private island — a manicured beach day with the ship as backdrop, barbecue included, tender boats shuttling you back for dinner. As a first cruise or a winter long weekend, it is hard to beat. Just know the water runs cooler in January than the postcards suggest.

Mega-ships and private islands

The Caribbean is home to the largest cruise ships ever built — floating resorts carrying six thousand guests, with neighborhoods, parks and ice rinks aboard. The lines compete on hardware, but increasingly they compete on private islands too: perfect-day beach clubs with the biggest slides and quietest lagoons in the region, reachable only by ship. If the ship is your destination, book the newest hardware on a Western route. If the islands are, book itinerary first and ship second.

Homeports: where Caribbean cruises begin

Miami and Fort Lauderdale (Port Everglades) are the twin capitals, with Port Canaveral close behind — all an easy flight or drive for most of the U.S. Tampa, Galveston and New Orleans serve the Western routes; San Juan opens up the Southern Caribbean without long sea days. Fly in the day before, always: the cheapest cruise is the one you do not miss, and a pre-cruise beach night is a fine way to start. For dates and weather, the timing notes below matter more than any other choice on this page.

Timing. Prime season runs December to April. Hurricane season runs June to November, peaking in September — prices drop, ships reroute around storms, and flexible travelers save real money. May is the connoisseur's month: warm seas, thin crowds, shoulder prices.