Best Places to Travel in May

Planning your spring or summer vacation? Here are the best places to travel in May.

May 2, 2017

May is an ideal time to travel to the islands. Memorial Day kicks off the summer season, and festivals celebrate everything from music to local cuisine to chocolate. It’s also a big time of year for sailing regattas around the globe, and even Carnival is still going strong in the Caribbean. Here are the best places to travel in May.

Best Places to Travel in May: Aruba


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You don’t really need an excuse to visit Aruba, but the Aruba Soul Beach Music Festival is a pretty good one. The five-day event kicks off on Memorial Day weekend and includes beach parties, comedy performances and concerts each night headlined by top artists. This year, Alicia Keys, Maxwell, Guy and DJ Jazzy Jeff are the main acts.

Best Places to Travel in May: British Virgin Islands

British Virgin Islands

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Over Memorial Day Weekend, more than 300 boats head to the BVI to participate in the Leverick Bay Poker Run. Captains compete for a cash prize by anchoring at pre-determined stops, like Scrub Island and Pirate’s Bight, to try to collect the best poker hand. Spectating is just as fun: grab a spot at Foxy’s Beach Bar on Great Harbour (one of the official stops) for live music, a beach barbecue and drinks concocted with Foxy’s Firewater Rum.

Best Places to Travel in May: Cayman Islands

Cayman Islands

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The first week of May means it’s time for Carnival on the Cayman Islands. Cayman Carnival Batabano celebrates Caribbean culture by bringing the streets of George Town to life with steel pan bands, floats and parades with thousands of people dressed in flamboyant, colorful costumes. The name is actually a nod to the island’s turtling heritage: Batabano is a word for the tracks that sea turtles leave in the sand as they crawl to the beach to nest.

Best Places to Travel in May: Tahiti


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One of the best places to travel in May for sailing are the islands of Tahiti, thanks to the Tahiti Pearl Regatta. Billing itself as “an ideal balance between a sporting competition and a festive discovery of the islands,” the four-day event invites yachtsmen to discover French Polynesia by sea. As if the islands weren’t enticing enough, optimal sailing conditions (regular winds, sun, no swell in the lagoons, small tidal range) are an added bonus.

Best Places to Travel in May: Oahu, Hawaii

Oahu, Hawaii

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Oahu takes the tradition of honoring fallen heroes on Memorial Day to a beautiful level with the Lantern Floating Hawaii ceremony. Each year, thousands gather at Ala Moana Beach on the South Shore to pay their respects to lost loved ones via floating lanterns. Each family receives one lantern to place into the water, with three sides where remembrances and prayers can be written before sending it off into the horizon. If you can’t make it in person, the event is also streamed live.

Best Places to Travel in May: Grenada


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Some of the world’s best chocolate is made here, and the Chocolate Festival is your chance to indulge. Bean-to-bar tours, cooking classes, and cocoa-laden menus offer plenty of tasting ops, with chocolate meditation and chocolate spa treatments to increase the glow.

Best Places to Travel in May: St. Lucia

St. Lucia

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The end of April brings enviable room rates and perfect weather (the sticky wet season is still a month or more away) — plus the St. Lucia Jazz & Arts Festival. Wherever you’re staying, you’ll likely find one of its 15 venues nearby. Each year the program is packed with big names (Jimmy Cliff, Diana Ross, and Ziggy Marley in past years), but much of the fun comes from discovering your own rising star.


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