The Caribbean is the world’s most popular cruise region — and the easiest way to sample a dozen sun‑drenched islands in a single week. Ships sail year‑round from Florida and beyond, and itineraries split three ways: Eastern (beaches and duty‑free shopping), Western (Maya ruins, reefs and Mexico), and Southern (the deep, less‑crowded islands).
The stops that make up a typical Caribbean sailing — tap any for things to do ashore.
Old San Juan’s blue cobblestones and the El Morro fortress — a favorite Eastern turnaround port.
Things to do in port ›Duty‑free shopping in Charlotte Amalie and the postcard sand of Magens Bay.
Things to do in port ›Two nations, one island — French cafes to the north, Dutch beaches and Maho’s jet‑spotting to the south.
Things to do in port ›The Western Caribbean’s reef capital — world‑class diving plus a hop to the Tulum ruins.
Things to do in port ›Stingray City sandbars and Seven Mile Beach; tender in to George Town.
Things to do in port ›Dunn’s River Falls, bamboo rafting and jerk on the beach.
Things to do in port ›Southern‑Caribbean sun outside the hurricane belt — Eagle Beach and desert‑island calm.
Things to do in port ›A frequent first stop — Paradise Island, forts, and quick beach breaks.
Things to do in port ›The sweet spot is December through April — warm, dry and calm. Hurricane season runs June through November; sailings still go (and prices drop), but pack flexibility with the weather. Cruise lines shift ships south in winter, so that’s when choice is widest.
Major lines cruising Caribbean:
Destinations Guild is an independent travel company and a proud partner of Trip.com. Book through our links and you pay the same price while the Guild earns a small commission that keeps our guides free. Cruise fares and sailings are shown live on Trip.com.