Destination of the Year: Key West, Fla.

Destination of the Year: Key West, Fla.

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After all these years and so many destinations have “come out” as gay-friendly, Key West retains the title of the quintessential LGBT travel experience.

Key West is simply fabulous — an island utopia that welcomes everyone, and a destination where a bicycle and a sarong are all that you could need for a week of relaxation. To understand why Key West is the destination of the year, all you really need to do is go back to its roots: guesthouses, water and sunsets.

Navigating your trip to rediscover Key West could be a challenge. Key West has indeed changed over the years. There are more cruise ships, larger airplanes, fewer gay bars and the drag scene is missing the “World’s Oldest Living Drag Queen”—Margo, or David Feldstein —who died in 2006. The Key West Business Guild is a terrific resource for LGBT travelers planning their trip.

Here are three ways I rediscovered Key West:

Stay at a guesthouse

To experience the true spirit of Key West hospitality, stay at a Key West guesthouse. The island does offer super-exclusive accommodations and upscale international hotel chains. This destination prides itself on good service to the guest, and there are exceptional guesthouses in Key West. Alexander’s Guesthouse and Big Ruby’s are terrific choices for gays and lesbians, especially when traveling together. New Orleans House, Equator Resort and Eden House are just a few of the great choices for the gay, LGBT and all-welcoming guests.

The Best Gay Guesthouse in 2012 is the Island House. Always offering top-notch service with a consistent and well-trained staff, Island House retains the allure of gay-male travel. It is a destination within a destination. Offering an all-male environment and luxury rooms, fine dining, entertainment and great conversations, Island House delivers superior service. The resort offers great deals for free stays off-season when you buy a winter escape. See for more information and to book your stay.

Explore the water and sea life

Dolphin Safari Charters is the perfect small-ship excursion. Super friendly and handsome Captain Gary (originally from South Africa) leads this voyage into Key West’s pristine waters. Offering a very private and VIP trip experience, Captain Gary is part teacher and part fun-seeker. Dolphin sightings are almost guaranteed on every trip and a sighting is where the fun begins. A three-plus-hour trip costs $89 plus tax and gratuity per person. The dock is located at the Banana Bay Resort and Marina and includes free parking. Trips are offered each morning and afternoon. To find out more, visit

Celebrate the sunset

Of course, Mallory Square is the place to toast another perfect day and sunset in Key West. Danger Charters Wind & Wine Sunset Sail is a perfect way to celebrate Key West’s legendary sunsets. Danger Charter boats are custom-built replicas of a type of American sailing craft called a Skipjack. Simply catch the boat at Westin Hotel on Mallory Square for a two-hour sail into a romantic sunset. For about $95 per person (including a generous tip), the ship’s exceptional and friendly crew share with guests an impressive wine and beer selection from around the world. To book your voyage, visit

Mark your calendars

Gay Spring Break takes place this March and April. Visit Key West Womenfest is held Sept. 4-9. Visit

Getting there

It is getting easier to get to Key West. Cape Air, US Airways, Delta, Southwest and American Airlines offer service from key gateway cities. According to, fares range between $300-$600 roundtrip to Key West.

Jeff Guaracino is the author of “Gay and Lesbian Tourism: The Essential Guide for Marketing” and the co-chair of the International Gay and Lesbian Travel Association.

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