Metro Weekly

Key West: 12 “Must Dos”

3. Hunt Hemingway

The great American writer’s ties to Key West are legendary. Visitors have the unique opportunity to trace his life on the island. The main attraction is the Ernest Hemingway Home & Museum, where he lived with his second wife Pauline from 1931 to 1939. Captain Tony’s Saloon and Sloppy Joe’s Bar each lay claim as Hemingway’s official watering hole. For more than three decades, Sloppy Joe’s has hosted the annual Hemingway lookalike contest as part of the island’s Hemingway Days celebration. In addition, there’s a permanent exhibit about Hemingway’s impact on Key West at The Custom House Museum.

Photo by Troy Petenbrink

Photo: Troy Petenbrink

Of course, Hemingway is not the only literary giant to call Key West home. For more than 30 years, gay playwright Tennessee Williams lived in in the city. The Academy Award-winning film adaptation of Williams’ play, The Rose Tattoo, was shot on the island in the ’50s, and the Tennessee Williams Theatre opened in 1980 with the world premiere of his play, Will Mr. Merriweather Return From Memphis?

4. Taste the Island

Often a destination is defined by its food, and Key West is no exception. By far its most famous eat is Key Lime Pie. The story goes that the dessert, made of Key lime juice, egg yolks, and sweetened condensed milk in a pie crust, was created by a sponge fishermen sometime in the 1800s. From then to now, the pie has become an island must have, and some of the best can be found at Kermit’s Key West Key Lime Shoppe, Key West Key Lime Pie Co., and Blue Heaven Restaurant.

Photo by Troy Petenbrink

Key Lime Shoppe – Photo: Troy Petenbrink

Other Key West signature dishes are conch fritters (Half Shell Raw Bar and The Conch Shack), as well as Key West pink shrimp (The Flaming Buoy Co. and Garbo’s Grill). The annual Key West Food and Wine Festival is a great opportunity to explore the island’s culinary offerings. 

5. Enjoy Your Accommodations

There are plenty of hotels and guesthouses to meet nearly any taste in Key West. For those seeking a large full-service property, the Hyatt Key West Resort and SpaWestin Key West Resort, and Casa Marina Resort are fine options. All are TAG Approved gay-friendly. Among the boutique properties that draw a predominantly LGBT clientele are Alexander’s Guesthouse, and the all male resorts Equator ResortIsland House and the New Orleans House, part of Bourbon St. Pub.

Photo by Troy Petenbrink

Photo: Troy Petenbrink

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Troy Petenbrink is Metro Weekly's contributing writer for food and travel. He can be reached at

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