Best Places to Travel in May

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.


Watch Oracle Team USA defend their title at the 35th America’s Cup race. Teams comprised of the best sailors in the world will race their wing-sailed catamarans through Bermuda’s Great Sound. The event kicks off with the Louis Vuitton America’s Cup Qualifiers on May 26, then top challengers will compete on June 17 for the trophy.


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, Usher, The Roots, Mary J. Blige and Faith Evans are the main acts.

British Virgin Islands

Ogle classic beauties at Foxy’s Wooden Boat Regatta on Jost Van Dyke. While the crews are out racing, your job is to continue the party at Foxy’s Beach Bar. Non-stop live music and drinks concocted with Foxy’s Firewater Rum make it a snap.


Calling all foodies: sample the best that Indonesia has to offer at the Ubud Food Festival. During the three-day event, expect food and wine tastings and culinary markets, along with special events highlighting the best of Bali (think lunches overlooking the rice paddies). Southeast Asia’s most prominent chefs go head-to-head in cooking competitions, and lead master classes on topics like the power of coconut, Indonesia’s forgotten flavors and the secrets of Masala.

Cayman Islands

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.


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.

Oahu, Hawaii

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 North 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.


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.

St. Lucia

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.

Puerto Rico

San Juan’s Escambron Beach becomes more than just a spot to park a beach towel and swim in crystal-clear water when it sprouts a “tasting village” and transforms into the foodie fest Saborea. Celeb chefs, cooking demos, and lots of tastings (food and drink), with a kick-off party called “Bubbles and Bites”: Champagne paired with Puerto Rican chefs’ creations. We’ll drink to that.

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