Miami has its Calle Ocho; Miami Beach has Art Basel; Orlando has The Mouse; but it’s another popular Florida tourist destination that annually offers arguably the most colorful event in the tourism-driven state. Key West’s Fantasy Fest is an event unlike any other; a distinctly adult and distinctly Key West occasion each fall that draws tens of thousands of visitors from all over the world. The multi-day bacchanalia, linked to Halloween, was initially created as a means of attracting visitors during the tiny island’s one-time slow tourist season. Culminating in a parade unlike any other, for which residents of the notoriously colorful town at the continental United States’ “southernmost point” go all out in terms of creativity, edginess and occasionally even shock value, Fantasy Fest 2013 takes place October 18-27 and presents a deliciously subversive way to truly appreciate the culture of the odd island.

Themed “Super Heroes, Villains and Beyond,” this year’s celebration includes performances, nudist and fetish events, a street fair, ethnic celebrations, parties, a pet masquerade and parade and numerous other good-humored and colorful events that draw from Key West’s well-deserved Bohemian reputation. But despite the diversification from its earlier years, the headline event remains the Captain Morgan Fantasy Fest Parade on Oct. 26. Some 70,000 people are expected to be in attendance for the most eclectic and imaginative costume interpretations one will see in any parade in the nation. It is a distinct experience that begs for photography and videography because your friends back home just might not believe your description of the occasion.

For the parade itself, it is highly recommended to scout out your vantage point hours in advance of the event. The parade takes place along the island’s Duval Street – the little island’s major street and the center of virtually all tourism activity in town. Your best bet is to find a centrally located open-air bar (most bars are open air in the breezy port town) and a table near the street. This will enable you to indulge in Fantasy Fest’s two most popular activities – watching the colorful cavalcade of costumes and drinking. Don’t worry about arriving too early. It’s expected; a boon to local businesses, and Key West natives – “Conchs” as they are called – are notably friendly and unpretentious. The remainder of your evening will be the stuff of memories.

Outside of the Fantasy Fest activities, for an island protruding into the Caribbean, Key West is not bustling with tourist attractions. Fort Zachary Taylor, the underwhelming Hemingway Home and other historic sites are well marked and well marketed. There are no scenic or particularly practical beaches, which often surprises visitors; and strolling along Duval Street, visitors will see many of the same tourist-driven establishments one finds in most Caribbean tourist destinations. Central to the Key West experience is hunting among chain retailers for the remaining local shops featuring local art, crafts, kitsch and a little kink. If there were an official Key West activity, it would be barhopping Duval Street, checking out the art and enjoying countless venues for live music.

Fortunately, besides eclectic shopping on Duval Street, Key West’s restaurants and bars are also fun and occasionally even offer very good food. Locations not to be missed include Sloppy Joe’s, Hog’s Breath Saloon and Captain Tony’s for libations; and Caroline’s Café, Blue Heaven, Louie’s Backyard and Café Marquesa for delightful Florida-inspired cuisine. You will want to make sure to sample Key Lime Pie, Conch fritters and Florida lobster to experience local cuisine.

Given its memorable nature and spectacle, a visit to Key West for Fantasy Fest is a unique experience well worth anyone’s bucket list.

At A Glance

Access: Although served by a small airport, most visitors fly into Miami International Airport and rent a car for the 3-4 hour drive south to Key West – a terrifically scenic drive.

Population: Approx. 24,000

Climate:  Expect warm days virtually year round with slightly cooler periods December through February and potentially hazardous tropical weather in the late summer and early fall

Main Attractions: Tropical splendor in a distinctly laid-back Bohemian environment, visual arts, dining and offshore fishing

Hot Picks

Local Lingo: Key West natives are routinely called “conchs” and are proud of it. Just remember it is pronounced like “conks,” or it’s obvious you are from a distant land.

Wander: While most Key West attractions are on or near Duval Street, don’t be afraid to wander off the main drag. The tiny island is easy to walk, and there are often hidden treasures in the least expected places.

Wildlife: You’ll see lots of wild things in Key West, but a few are truly unique. The island is home to free roaming chickens, which make themselves at home most anywhere, and there are the so-called Hemmingway cats, a line of polydactyl cats descended from the author’s beloved feline.

Stay In Style

Pier House Resort and Spa is a classic, conveniently located resort featuring spectacular service sans attitude, plenty of amenities and knowledgeable staff members who can help make the best of your Key West visit.

Eden House is slightly off the beaten path but exemplifies the tropical boutique hotels and guesthouses that dot the island. An award-winning eatery, beautiful pool, scenic grounds and terrific personalized service have made it popular since it opened – the first hotel on the island.

Visit Online

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