Let the good times roll in the Caribbean

There’s always a party happening in the islands of the Caribbean, but some have a special twist. Join one of our cruises and you might be lucky enough to experience some of these events. Here are our five favorites.

PIRATES FEST, CAYMAN ISLANDS

If you thought pirates had long departed Caribbean waters, think again. Come November, a motley crew sporting bandanas, eye patches, and peg legs sail into George Town flying the skull and crossbones. And Caymanians are proud of their historic links with these seafaring scoundrels, partying and parading across the archipelago for a full three weeks. So, join in the merriment or risk being told to walk the plank.

Sail to the Cayman Islands in November 2026 on our cruise Fort Lauderdale Roundtrip.

HERMIT CRAB RACING, JOST VAN DYKE, BVI

The Caribbean’s very own species of hermit crab, Coenobita clypeatus, may be small – about the size of your fingertip – but it’s a competitive little critter. Jostling with its fellow contestants at the starting line (the middle of a table), once released, the quick-clawed crustacean makes a dash to be the first to reach the boundary of the circular racetrack. Catch the action at beach bars such as Foxy’s in Great Harbour, Jost Van Dyke.

Check out our cruises calling at Jost Van Dyke.

SALSA NIGHTS, PUERTO RICO

Puerto Ricans love to strut their stuff, especially to a salsa beat. If you do too, head to La Placita de Santurce in San Juan. This marketplace does swift commerce by day but on a Thursday and Friday night, it turns into a dancefloor where you can shake your hips and spin your partner with the best. Catch live performances of Bomba here, too, the distinctive Puerto Rican move in salsa’s mix, on Monday nights at La Terraza de Bonanza.

Check out our cruises calling at Puerto Rico.

OISTINS FISH FRY, BARBADOS

Fish fresh from the sea is the reason Barbadians and visitors alike head south to the port of Oistins on a Friday night. There can be few better ways to end the week than feasting on piping hot fried mahi-mahi or grilled flying fish cooked before your eyes at one of the many stalls. When you've had your fill, browse local crafts on sale and listen to live bands play calypso, ska, and reggae beats.

Check out our cruises calling at Barbados.

SHIRLEY HEIGHTS, ANTIGUA

There’s only one place to be on Sunday afternoons: Shirley Heights. This old military lookout point in the south of Antigua is the perfect place to take in a spectacular view, especially of English Harbour and Falmouth below, as the sun sinks below the horizon. It also hosts an impressive party where you can listen to live music while enjoying some delicious jerk chicken and a rum punch or two.

Check out our cruises calling at Antigua.