Our travel guides are frequently updated. This guide was last updated 10/06. Still, there are places that are bound to have closed or changed since our last update. Use the listed phone numbers to call ahead, and please let us know of any corrections or new places of interest you discover.
Key West has always been different from the rest of the United States or even the rest of Florida. Souvenirs jokingly display the flag of the "Conch Republic," and locals are proud of their defiant, if imaginary, independence.
Key West is set at the very end of the Florida Keys, the southernmost point in the United States, just 90 miles north of Cuba. The resort town has long been home to artists, authors, and other eccentrics who migrated here for the quaint, quirky and very laid-back atmosphere. Quaint and quirky remain the big attraction here, although the affectations of modern tourism have replaced some of the eccentricity with T-shirt shops and big straight nightclubs. Key West is not a big beach resort. There are a few large hotels on the beach, but Key West's focus is at the other end of town, and many tourists, particularly gay ones, don't ever see the beach.
Duval Street is the main drag, running the length of Old Town, and ending at the west end, where sunset is a major event every night of the week. The street is a mixed bag of commerce, with great stores and restaurants nestled among the tourist-trap T-shirt palaces. But walk a few blocks north or south of Duval and you can see (and spend the night in!) some of the charming architectural beauties that embody the seafaring history of the city.
Influenced by Bahamian and Cuban architecture, and the Greek Revival style of New England, these structures are a reflection of maritime trade routes, and more than 2,000 of them are on the National Register of Historic Places. The architecture and foliage of Key West align it more closely with the Caribbean than Orlando, and it is the Caribbean feel that makes Key West such a vacation jewel.
For gay travelers, Key West once reigned as the gay vacation mecca, so much so that other resorts are often called "The Key West of the North" or "The Key West of The West" to proclaim their gayness. The development of other gay destinations and vacations has eroded the resort's previous monopoly and eclipsed some of its offerings, particularly nightlife.
Key West's reign has also been diminished by the continued influx of daiquiri-guzzling straight tourists who arrive on cruise ships and fill the low-end chain motels on the outskirts of the island -- which aren't even particularly cheap any longer. Although those who have made multiple visits may feel some nostalgia for gayer days, there's still enough charm to seduce all but the most jaded of travelers. The elements that earned Key West's reputation are evident -- fine restaurants, a restful, laid-back atmosphere, abundant water activities, and one of the world's largest and most varied collections of gay accommodations.
Days spent poolside or on the beach are truly restful here, and lack the attitude of South Beach or Provincetown. The island is particularly well-suited to couples in search of a romantic getaway.
Don't pack anything dressy (a polo shirt is the most you'll need in the fanciest of restaurants); book yourself into a quaint inn or guesthouse; rent a bike instead of a moped; and bring few expectations except that of relaxation.
Chances are you'll quickly settle into the laissez-faire Key West attitude. We know you'll sleep well and eat well; the rest is up to you.
Part One | Part Two
Key West: Where to Stay
Key West: Where to Eat
Key West: Where to Play/Meet
Key West: What to See and Do