Known to locals as the “Conch Republic,” this smallish — 2-by-4 mile — cay at the southernmost tip of Florida is a fantasy island for many, filled with an entertainingly odd mix of deadheads, drag queens, sloppy drunk frat kids, fussy older gentlemen, a sprinkling of literati, cats with six toes and gay strippers. What more could you want from a Florida resort town?
First, some fun facts: The locals attempted to succeed from the USA in 1982 — hence the “conch republic” moniker. Famous past residents include some world-class eccentrics like Tennessee Williams, Ernest Hemingway and Jimmy Buffett. Known today as a gay-friendly town, tolerance has been a part of life in Key West long before the first rainbow flag was hoisted. Sandy Cornish came to Key West as an ex-slave in 1840, and after a successful farming career he died the richest man on the island. And in 1832 the island’s own Barbara Mabrity became one of the first women in America to manage a lighthouse.
All very interesting, but what are the best things to do in Key West today? Here’s our NewNowNext 9 for the southernmost city in the continental US.
Captain Gary, and his shipmate canine “Katie”, runs Dolphin Charters the most intimate, non-commercial, wild dolphin sightseeing tour on the Island. Originally from Zimbabwe, Captain Gary operates his tours with the love and the intensity of a game ranger in the African bush. He spots dolphins from an improbable distance and carefully approaches a pod so as not to disturb them. As the boat buoys among the pod, he lists each dolphin by name and recognizes when they need some space. It is an amazing site to see them playing, mating and eating in the middle of the ocean — up close. His best sighting so far has been 27 dolphins in one outing. At the end of every tour, Captain Gary wraps things up with a quick snorkel stop before heading back dry land.
2. Dinner and Drinks like a Local
One hears stories about the hippie-filled Key West of decades past, about those who traveled and stayed behind, never to wear shoes again. Dinner at BO’s Fish Wagon will allow a glimpse into that past. Started as a fish truck on Duval almost three decades ago, BO Fish Wagon is the kind of place where you share tables with old timers who say things like “that was before the Dead went mainstream.” BO’s serves the day’s catch served up deep fried on Cuban bread, unpretentious and delicious.
The Friday night jam at BO’s Fish Wagon is arguably the the best live music on the Island. Barry Cuda and the Sharks dish out blues classics on a piano, base and drums that have been wedged between the picnic tables and nautical kitsch, as genuine Key West as it gets.
If you’re looking for a slightly racier late night drink, Bourbon Street Pub is the other side of genuine Key West — site of the annual “heel drop” on New Year’s Eve (see video) and home to some of the hottest male ’dancers’ in town along with the best drag shows. In town on Saturday night and feeling sexy and a little bit lucky? Or just really drunk and not able to make excellent choices? Either way, make a bee-line for Bourbon St to enter their weekly amateur stripper contest — winner gets $50 in cash AND a $50 bar tab. Oh, and if you’re really good, they’ll let you keep dancing all night for tips. Bad decision = new career? Who can say.
3. The Waldorf Astoria Resorts
The amount of white sand beaches in Key West is limited and the Waldorf Astoria properties, the Reach and Casa Marina, have nabbed a large chunk. The Reach is located on one the island’s only natural beaches and Casa Marina has almost a quarter mile of prime, albeit rocky, beachfront. A pleasant mix of city dwellers escaping the hustle and European tourists hang out by the two beach front pools or lounge in hammocks among the palms. The poolside cocktail menu is surprisingly inventive. The blueberry tarragon gin and tonic, in particular, is unexpectedly yummy. For more secluded luxury, book a ground floor patio room at Casa Marina and you’ll have your own waterfront paradise. Guest of either property are free to use the amenities of the other, making the more affordable Reach a serious value.
4. Jazz at Gardens Hotel
On Sunday afternoons those in the know head to the Gardens Hotel for their “Jazz in the Garden”. The perfect way to spend a chill afternoon, enjoy some excellent music and a drink by the pool. The wine kiosk is a self serve sampling of good wines and as everyone is encouraged to “pour what you will,” big gulp sized glasses seem to be the norm. Music aside this is also an enjoyable way to experience one of the loveliest small hotels on the Island.
Why has no one made coffee, chocolate fondant cake iced cream? Turns out they have. It’s a mystery that the chefs at Café Marquesa have unlocked, in the most decadent and delicious way imaginable. Chef Susan Ferry presents a daily menu of mostly local dishes that are tastefully refined for laid back Key West. It’s got the atmosphere of a New York restaurant — think Grammercy Tavern — but in the tropics. The 50-seat restaurant also has a small bar, known for its signature martini creations.
6. Petronia Street
Duval street is the most famous street in Key West and while it still has some interesting hot spots like 915 Duval (one of the island’s better restaurants), the T-shirt shops and Hard Rock Cafés have cast a tacky shadow over this famed street. Enter Petronia street, a cross street to Duval that ends in the Bahama Village, which has a far more local, less aggressively touristy vibe. The best known establishment on Petronia is Blue Heaven, which is so famous you might think it is a tourist trap, not at all. A former cock fighting rink and brothel, Blue Heaven serves fresh and tasty breakfast to the hung over and road weary: Beer-batter pancakes, pink shrimp benedict and the biggest slice of Key Lime Pie on the Island. Free roaming roosters and chickens accompany the live music — a one man Pink Floyd tribute band.
As you waddle out of Blue Heaven check out the great shops located just outside, Wanderlust sells a mix of designer clothes, local art and accessories. Besame Mucho (pictured) is a bohemian hodgepodge of high-end natural beauty products, artisanal candies and chocolates, luxury home goods and handmade jewelry and clothes.
Once you have worked up your appetite again check out the Conch Shop to get conch served in everyway imaginable or the new kid on the block Santiago’s Bodega.
7. Shop at Evolution
Evolution is the place to get fashionable albeit at somewhat expensive pricing. They have all types of colorful, well-designed beachwear from baggie board shorts to so-tight-you-can-see-the-BEEEP shorts from 2Xist among other labels. The staff is super friendly and knowledgeable not only about tight fitting swimwear that will tell everyone your religion at a glance, but also about the latest island events, gossip. etc.
Key West is known for seafood and maybe a little Cuban fare, however, it turns out some of the best Mexican is served up at the tiny and unassuming Bad Boy Burritos – the fish tacos will change your life. Husband and wife team Chris and Erin have created a seasonal menu of local and fresh produce that make up some amazing burritos, tacos and ceviche. It’s a great place to grab some food and head to the beach or a park. They also own two cents restaurant, a cool kids spot off the tourist track.
9. Gay it up at the Island House
Last but hardly least, for a strong shot of gay, head to this, the best of the clothing optional joints in town. This friendly (but not, however, female friendly), gay owned and operated guesthouse in Old Town, has a secure private compound with a central courtyard where men in various states of undress — mostly dressed, frankly — lounge around poolside, grab drinks, chat with friends, eat food (not as odd as it sounds, and generally pretty delicious) and just hang out. Clothing optional can seem all wrong in theory, but it’s not creepy at all. It’s very casual not predatory, and can get amusingly raucuous around happy hour…when the drinks are on the house.
All images courtesy Jason Rowan