Ocho Rios, Jamaica
The promoters of the Ocho Rios Jazz Festival want to emphasize two things this year: first, that the festival will highlight world jazz, and second, that all of June is jazz month in Jamaica. Our take: When island promoters invite you to share their taste in music and elysian location for a month, it's best to simply accept, no questions asked
(www.ochoriosjazz.com)

Bonaire
If you're in Bonaire, chances are you like diving or (at least) snorkeling, which means you've probably gawked at someone else's pretty underwater photography and thought, "I gotta learn how to do that." Now's your chance: Each June Bonaire hosts the Bonaire Dive Festival, which includes a Digital Shootout, with seminars and access to some of the world's top underwater photographers. Oh, and $10,000 in prizes for best underwater shots (contest open to all levels).

Chincoteague Island, VA
Summer has finally made its way up to the Delmarva Peninsula, and this spot offers an eclectic mix of why you go to the beach: the Chincoteague National Wildlife Refuge, comprising more than 14,000 acres of beach, maritime forest, and marsh; an expansive, calm sound inside the barrier island; scenic boat harbors; waterfront seafood restaurants; and a slightly slower pace of life than you tend to get in points immediately north.

Bahia Honda Key State Park Beach, FL
A lot of people will dismiss Florida in June as too hot. But a lot of people tend to be wrong: The Keys often enjoy a soothing summer breeze and the water—oh, somewhere around 80 degrees—is right where you want it. Add in a rare stretch of soft sand on the otherwise rocky lower Keys, no beachfront property, and shifting sandbars 100 feet out where those in the know drag their beach chairs to take relaxation to the next level, and all you need is a cool drink to make your day complete. Walk to the north end to discover a vast field of live conchs in the shallows.

Nauset Town Beach, Cape Cod, MA
June brings the first real sense of summer to The Cape—barbeques on the beach, the country's best summer-league baseball, frenzied fishing, and warm days—but the crowds don't arrive in force until July. The beach is part of Cape Cod National Seashore, which protects it from kitsch and over-development. If you get lucky, gray seals will pop their heads above water to check you out. Yes, the ocean here is still c-c-c-cold in June, but so is the beer at the Land Ho!

Seven Mile Beach, Grand Cayman
Most people come here to dive, party, dive again, and then party some more. June brings an added bonus: painting! Rogest Art Down Under week lets some of the world's top marine-life artists show off their skills and help aspiring diver/snorkeler/painter types improve theirs. There are painting contests, raffles, wine and cheese events, and—of course—diving, partying, diving, partying, diving…

Paradise Island, Bahamas
Just the name of this festival—Junkanoo—sounds wild and freewheeling, and Bahamians decided that their primary Junkanoo late December through early January was so much fun that they needed another one halfway through the year. Summer Junkanoo runs June and July, highlighted by a Mardi Gras-like parade, complete with massive teams of costumed revelers singing, dancing, and performing music. There's also a street party every Friday during Junkanoo at Woodes Rodgers Walk (around the main harbor) and delectable food and other celebrations of Bahamian culture throughout the festival.

Saint Pete Beach, Saint Petersburg, FL
The story line here is simple: Beautiful, wide beach, warm Gulf of Mexico waters, sky-fire sunsets, and an eclectic crowd (Florida is not just for old folks anymore). The most prominent structure on the beach is the majestic Don Ceasar Hotel—worth a walk-through even if you stay elsewhere—and a lot of the fun is tucked into the revitalized downtown, which harbors hip bars, cafes, museums, quirky stores, and more. Need an excuse for June? June's John Levique Pirate Days, just north in Madeira Beach, celebrates the region's privateer history, and the Taste of Pinellas at Vinoy Park on the bayside of St. Petersburg is the Tampa Bay area's largest annual food festival.

Frigate Bay, Saint Kitts
Set on opposing sides of the stem of Saint Kitts, South Frigate and North Frigate offer very different beach experiences a mere ten-minute walk apart. South Frigate faces the Caribbean, with (usually) placid blue waters nudging onto powdery sands. The north side stares down the Atlantic, with darker sand and typically wilder water, and is often called the island's most scenic beach. Both serve as fitting warm ups to a night of live music, which brings us to the Saint Kitts Music Festival. The event features a wide variety of artists—jazz, rock, reggae, pop, hip hop, and more—so you have a good chance of catching at least one act you like.

Bagni di Tiberio, Capri, Italy
The space is small, and the sand more grey than white, but the soothing Mediterranean and the intoxicating Italian culture—brightly colored fishing boats, seaside restaurants, and hilly scenery—will sweep you away.