Calendar Highlight: The annual gay Get Wet weekend in late September has parties, beach outings, and movie screenings under the stars.
The 411: Floating serenely about 40 miles north of Venezuela on the outer fringe of the Caribbean's hurricane belt, Curacao is the arid, hilly government seat of the five-isle Netherlands Antilles. Candy-colored Dutch architecture lines the capital city of Willemstad, where a floating pedestrian bridge connects the 17th-century tourist-centric Punda district with the now-gentrifying 18th-century Otrobanda section. Dutch influences permeate the culture, but most of its 138,000 residents also speak a local Creole as well as English and Spanish. History and culture vie for attention with Curacao's 35-plus beaches and, only a few fin kicks offshore, a kaleidoscope of coral reefs.
How Gay?: There is only one full-time gay bar -- Lyrics, in Willemstad -- but the island mantra Biba i laga biba ("Live and let live") and a three-year-old gay tourism push make Curacao one of the Caribbean's most queer-welcoming destinations.
Insider View: "We've learned from our ancestors how to dictate our own steps and don't let outside forces -- money, tourism, Holland -- do that for us. That is why we've maintained our cultural heritage." -- Kurt Schoop, founding member of the LGBT event producer Curacao Gay Plasa
Don't Miss: Rent a car to spend time in Banda Abou in the less-populated northwest, where postcard-perfect beaches like Cas Abou and Kenepa hug the coast and marigold-colored 17th-century plantation houses share the terrain with giant kadushi cactus.
Luxe Lodging Pick: Gay-owned Hotel Kura Hulanda Spa and Casino has 80 upscale rooms, a lagoon pool, and four indoor-outdoor restaurants tucked into a UNESCO World Heritage site of 65 multihued 18th-and 19th-century Dutch buildings.
Calendar Highlight: October sees both the Grape Harvest Ball and the Apple Harvest Festival. Over 350 different apple varieties grow on the organics-obsessed 74-square-mile island.
The 411: The largest of the Southern Gulf Islands sits between British Columbia's mainland and Vancouver Island. Funky, tolerant Salt Spring has long attracted those in search of safe harbor. Settled in the 1850s by disappointed gold prospectors, the island traces its black history back to 1857, when a group of nine African-American slaves landed at Vesuvius in the north of the island. The 20the century added communities of Japanese fishermen, hippies, artisans, queers, and U.S. draft dodgers, creating the idiosyncratic Salt Spring of today. The forested island's main town, Ganges, home to 6,000 of the island's 10,000 residents, offers several good inns and restaurants as well as a motley array of quirky and quaint options, including gay-owned B&Bs. Produce stands selling honey, flowers, eggs, and apples line island roads. Turn off those roads and discover 22 sandy beaches and many vineyards responsible for increasingly good Pinot Noir.
How Gay?: Salt Spring has a prominent LGBT population, many of whom join in events organized by GLOSSI, the island's gay and lesbian group. A small but perfect pride celebration takes place in September with an art show, concert, picnic, and dance.
Insider View: "When I take the ferry back home to Salt Spring, I feel like kissing the ground on arrival. Where else can I live in such beauty, eat great food, start a wacky business, and feel surprised when I encounter someone homophobic?" -- Julia Grace, artisan cheese maker of lesbian-owned Moonstruck Organic Cheese
Don't Miss: Thousands descend on Ganges's famed Saturday market to stock up on food, crafts, and art, all of which must adhere to the strict "make it, bake it, or grow it on a Gulf Island" rule.
Luxe Lodging Pick: By far the island's most luxe lodgings are at the Hastings House Country House Hotel -- an 18-suite luxury hotel, spa, and restaurant set on 22 acres on Ganges Harbor.
Calendar Highlight: November is the sunniest month of the year -- and among the driest -- on this exclusive and remote Brazilian island. With no rain to kick up sediment, the water is especially clear for diving.
The 411: Two hundred miles off Brazil's northeastern tip, this former island penal colony was fought over by the British, French, Dutch, and Portuguese for centuries. Few Americans know of this spectacular 21-isle archipelago, its only inhabited island being volcanic Fernando de Noronha, home to only around 2,100 people and a handful of bars, shops, and restaurants. The archipelago's environmentally protected status, distance from the mainland, and expense keep tourism at bay, though demand still outstrips its official limit of 400 visitors at any one time, with a long waiting list. (Celebs like Naomi Campbell, Calvin Klein, and photographer Mario Testino vacation here.) Lodging is found among 100 tiny posadas -- most are private residences -- yielding only a few hundred rooms altogether. Dramatic, jagged black cliffs jut out along virtually abandoned beaches, their higher points coated with tropical vegetation that reaches into the island's verdant jungle interior, nearly 70% of which is declared off-limits to development. The archipelago's crystal waters and exotic fish and turtle species make the islands among the best dive spots on earth.
How Gay?: With so few visitors, the island is not very gay, but you'll come across gay staff at hotels and gay cognoscenti from Brazil and beyond.
Insider View: "I must say it's one of the most beautiful islands in all of Brazil. The sea is very clean and clear. I recommend combining visits to the island with gay-happening cities on the mainland like Recife, Pernambuco's state capital." -- Dan Littauer, owner, gay travel company G Brazil
Don't Miss: Dolphin Bay, on the northwest side of the island, is home to spinner dolphins that congregate in numbers unmatched virtually anywhere else on earth.
Luxe Lodging Pick: With architecture and environmentally conscious grounds integrated into sea cliffs, the most exclusive resort is the Pousada Maravilha. Just three deluxe apartments and five private, isolated bungalows are scattered around a main lodge.
Calendar Highlight: From December 7 to 9, the Christmas in Edgartown celebration hosts cocktail parties, concerts, a Christmas Ball, and a chowder contest.
The 411: Often overlooked by gay travelers in their haste to get to nearby Provincetown, this 100-square-mile island is just 45 minutes from the mainland via a ferry that runs year-round from Woods Hole, Mass. The isle has long been a haven for discerning travelers like the Clintons, Carly Simon, Spike Lee, and Sharon Stone. Winter shows the Vineyard at its frosty finest, without the crowds and traffic snarls that clog up the island in summer. (The winter population drops to 15,000 from summer's clamorous 75,000 or more.) The weather is perfect for brisk walks to the lighthouses and cozy drinks by the fireplace in a historic inn.
How Gay?: With the advent of same-sex marriage in Massachusetts, Martha's Vineyard has become increasingly popular with gay travelers as a honeymoon escape. Although gay-specific entertainment options don't abound, a duo of elegant gay-owned inns, Lambert's Cove Inn & Restaurant and the Shiverick Inn, provide excellent accommodations.
Insider View: "My husband and I love winter on-island. It feels like we have the whole island to ourselves." -- Stuart Smithe, designer and frequent visitor
Don't Miss: Spend a crisp winter morning at the wonderfully peaceful Mytoi Garden, a 14-acre Japanese-inspired hideaway in the Nature Preserve on Chappaquiddick, a tiny island accessed by a two-minute ferry ride from Edgartown.
Luxe Lodging Pick: The 15-room Lambert's Cove Inn in West Tisbury is a luxurious boutique hideaway. This sophisticated gay-owned property boasts Thyme's eucalyptus-scented amenities, 500-thread-count Egyptian-cotton linens, and feather beds. And the inn's 70-seat restaurant features an outstanding contemporary American menu.