Key West: Home to Womenfest and lesbian-friendly relaxation

Editor’s Note: The below is our 2015 review of Key West’s Womenfest, which runs this year from September 6- 10th. It’s still not too late to book, if you’re looking for a last-minute chance to soak up the remaining rays of sunshine with your lesbian squad! Marcie Bianco highlights the event from her own travel experience, with tips on where to stay, what to do, and see, and eat. Here is an updated link to this year’s womenfest

The Sunshine State has a place for queer people to call their own: Key West. Since the early twentieth century, Key West, in particular, has served as an oasis for the gay community, as well as artists, writers, and those seeking an alternative to a mainland mentality. Ernest Hemingway bought a property there in 1928, and Tennessee Williams made a home there beginning in 1941. In between the arrival of these male literary titans was lesbian poet Elizabeth Bishop, who moved there in the late 1930s, renting an apartment at 529 Whitehead Street and later buying a house on White Street, where she lived until 1946.  “The island starts to hum/ like music in a dream,” she wrote in the poem “Full Moon, Key West,” evidence of how smitten she was of the island in the “glittering Gulf.”

The Florida Keys, and especially Key West, provide the quality of solitude necessary for those of an artist temperament who seek inspiration from the beauty of a tropical environment. The approximately 1,700 island archipelago of the Keys, with their endless florid sunsets, offers such a place. As the southernmost point in the continental United States, Key West by its very nature imparts a sense of detachment—for those wanting to “get away” and “cut loose,” from the daily grind where being gay is OK, there is arguably no better place in the U.S. to be.


Key West, too, has traditionally been the “key” for lesbians. Despite the increasing assimilation and gentrification (and heterogenization) of LGBT spaces, ladies still have their lesbian-centric Womenfest in September, which features the Kelly McGillis Classic Flag Football Championship, and a slew of other women’s events.

Flying into Miami International Airport (on American, which offers a number of direct flights between New York City and Miami daily), you can easily and cheaply rent a car at MIA (Budget offers compact cars for $17/day) and drive to the Keys via the Overseas Highway, one of the most scenic drives in the U.S. Otherwise, if your goal is to zip into Key West for a steamy, quick weekend, you should take the hopper flight from Miami to Key West International.

A little less than two hours south of Miami you’ll come upon the charming Islamorada, “Village of Islands,” which is the halfway mark between Miami and Key West. It’s worth stopping here to fuel up the car and yourself. Tucked away on the north side of Route 1 is  Amara Cay, a stylish newly renovated and reopened resort that offers travelers a surprising touch of elegance and urbanity in the area’s other more traditional accommodation offerings. Here you can swim in the pool or, via Amara Cay Resort’s private beach, jump right into the warm Atlantic and frolic among the pelicans, who are mesmerizing to watch in flight or during their feeding routine, in which they dive-bomb into the water to scoop up the plentiful fish. For more water sport activities, such as canoeing and paddle-boarding, take a five minute ride in Amara Cay’s private shuttle to their sister hotel, Pelican Cove, for complimentary access to their beach amenities.

AmaraCay1Photo by Juan Fernando

As part of its transformation into a premier property, the Amara Cay is reaching out to the LGBT community as desired clientele. Consequently, the Resort pays attention to details: enviable design flourishes in the lobby; masterfully mixed cocktails; and a restaurant that’s date-night worthy. Oltremare is some of the best fine dining you’ll find in town, which is evinced by the fact that locals dine there nightly to explore the creations of the very dedicated Chef Dario, who sources the freshest local ingredients for creations such as Cedar Key clams, conch, snapper—all given a Mediterranean touch.

Before you leave, and to witness  a spectacular sunset on the Gulf Side of Islamorada, drive a few minutes north on Route 1 to The Beach Café at Morada Bay, known for its frosty cocktails and fish tacos, but I recommend ordering their local-caught pink shrimp, blackened with some spice on a salad—simply delicious.


From Islamorada, continue south on Route 1 to Key West, which is about a two-hour drive. For lunch, stop at Keys Fisheries, Market and Marina in Marathon for its “world famous” lobster reuben sandwich. THIS SANDWICH IS A BEAST. It is filled with huge lobster chunks and is served with the essential fatty sides of fries and coleslaw. Nom away like it’s your last meal—because after you eat it I guarantee you won’t be wanting any more food for the rest of the day. Although you will be tempted.

Continuing south, about 20 minutes before you arrive into Key West you’ll hit the best beach in the Florida Keys: Bahia Honda State Park. YOU MUST SWIM HERE. The funny thing about the Keys is that while they’re surrounded by water—the Atlantic Ocean on one side and the Gulf of Mexico on the other—there isn’t a lot of public beach access and, when there is, the tides, the weather, and the season will determine whether or not you want to take a dip. Bahia Honda, nestling the joint where the two main bodies of water meet, has gorgeous turquoise water. The beach is inside a state park, so there are showers and restrooms, and there’s even a gift shop. (Advice: The beach spans the length of the park, but the best, clearest and cleanest, part is toward the south; this means turn right upon entering the park.)


From my days of being a baby gay in the early aughts, I had always imagined going to Key West and staying at the only lesbian B&B in town: Pearl’s. Well, my #DeepLez sisters, Pearl’s is unfortunately now closed, and the only LGBT exclusive guesthouse in Key West is Alexander’s. Most places, are, however LGBT friendly, especially the Marriott. My wife and I stayed at the Silver Palms Inn & Suites, which is newly renovated, affordable, offers free continental breakfast, and, yes, has a pool. Silver Palms is located on Truman Street, and is about a 10 minute walk from the Mardi Gras-like madness of Duval Street.  


While Pearl’s was sold to a property investment group that purchased properties in Key West including three gay properties, which are now operated as “all welcome,” the company has decided not to target the LGBT community directly. Their loss is our gain, because Mey Espinoza, the former General Manager of Pearl’s, has moved over to Silver Palms Inn & Suites and she gave us a very warm welcome. We hope that more lesbians, knowing that there is a proud and powerful hospitality maven at the helm, will make it their property of choice while visiting Key West. But it’s a sobering reminder: Many travel destinations which are high on the queer list, such as Key West and Provincetown, don’t become gay-friendly by rainbow magic. It takes our support, so be sure to keep your summer going and check out Womenfest in Key West next year!

While this year seemed less well-attended than previous years, the programming still offered pool parties, happy hours, a wine tasting, gallery opening, sailing adventure, drag shows—both kings and queens—dance parties, bingo and brunch. We were unable to attend all the events because there was so much Key West adventure to experience in one short weekend. But the women we saw were having a good time, and the only thing that could improve it would be even more women. The good news is that Key West, being a little queer at its core (it is, after all, known as the Conch Republic, and that vagina-like shell seems to be everywhere you look) still has a strong LGBT community. A gay business guild is the organizer of Womenfest and other events including Key West Pride. There is also an official gay tourism website to help you plan your own lesbian adventure.


There are some things you must do in Key West at any time of the year: (1) Go to Ernest Hemingway’s house and play with the 50 six-toed kitty descents of his very own six-toed cats. (2) Go to the Butterfly and Nature Conservatory and be whisked away into an enchanted fairytale land, filled with a variety of butterflies, birds, and even two flamingos! (3) Make a pilgrimage to the Southernmost Point Buoy, which marks the southernmost point in the continental U.S., and look outward—you’re only 90 miles from Cuba! (4) Have a dinner date with your girl at Azur and brunch at the fantastic Banana Cafe. (5) And have a piece of frozen key lime pie on a stick from Kermit’s, even if it kills you.


If you’re looking for elegance and exclusivity  in Key West take a six-minute ferry to Sunset Key, home to a luxury resort which has the best beach in Key West. It also arguably is home to the finest dining experience in town. Half of the very small island is owned by homeowners, the other half is allocated for rentals of one-, two-, three-, and four-bedroom cottages. Having gotten a tour of all these types of cottages, I think they would make excellent accommodation for a number of gatherings, from DIY queer writers retreats to marriage parties. Otherwise, this is a splurge for your wedding day.

Key West is an optimal destination for east coast residents looking to get away without leaving the mainland—and without breaking the bank. Womenfest is in September, so some restaurants and stores are closed for vacation, before reopening their doors for the busy high season, in fall and winter. Prices are higher in high-season, so going in late summer offers you a  sunny payoff in the Sunshine State.

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