Set smack between Miami and Havana, Key West plants its island charms on American soil. Sunset sails, hand-rolled cigars and a relaxing vibe are the evergreen allures that hook groups on this southernmost city and island in the continental U.S.
“You get all the benefits of going to a Caribbean destination without leaving the States,” says Stacey Mitchell, director of sales for the Florida Keys and Key West Tourism Council, and Key West resident for over 20 years.
“Corporate folks come down and it’s a playground because they come from an environment of suits,” Mitchell continues. “Whether president or CEO or clerical staff, everyone walks around in shorts, T-shirts and flip flops. The political office pecking order vanishes. Everyone is the same here. It’s a bond you can’t buy.”
Sun, sand and snorkeling are just a few of Key West’s star attractions. On the cultural side, despite its modest size, Key West looms large in the literary world, and served as a muse for two of its greatest players. Ernest Hemingway purportedly penned A Farewell to Arms while living above the showroom of a Key West Ford dealership, and Tennessee Williams is said to have written the first draft of A Streetcar Named Desire while staying at the La Concha Hotel.
Today, Ernest Hemingway’s home is one of the island’s most visited sites, frequented by 60 descendents of his famous polydactyl cats. Key West visitors can also meander through the tropical garden at the Heritage House Museum & Robert Frost Cottage, where the poet usually stayed during his winter visits. The garden was once a hangout for Tennessee Williams and Gloria Swanson, among other Key West celebs.
The Key West Literary Seminar, held each January, attracts the likes of Margaret Atwood and Ian McEwan.
“The literary festival does for Key West what Robert Redford did for film in Sundance,” Mitchell says.
While the literary history garners the headlines, Key West also nurtures a vibrant arts scene, including a variety of galleries that feature everything from Haitian art to photography. Cuban art, food and music also play into the equation, as about half the residents near the turn of the last century were of Cuban origin. For culinary buffs, Key lime pie, born in the Florida Keys, is the delicacy at Kermit’s Key West Lime Shoppe, among other locales.
On the adventure side, kiteboarding, paddleboarding and kayaking are a few options, while the water can also be experienced with an eye on conservation. This year NOAA (National Oceanic and Atmospheric Association) opened the Florida Keys Eco-Discovery Center on the Truman Annex waterfront, featuring exhibits about the Florida Keys National Marine Sanctuary.
On land, Key West features an extensive historic district, called Old Town, filled with quiet lanes and an abundance of ghost stories. Walking tours of the city’s above-ground cemeteries are popular, as are history rides on the Conch Tour Train.
The commercial center, Duval Street is bookended by the Southernmost House, a colorful old yellow Victorian mansion, and Mallory Square to the north is a popular spot for sunset.
Despite growth in an area called New Town, Key West retains its small-town village atmosphere, according to Mitchell: “We almost have the vibe of a Greenwich Village or SoHo—a small, compact environment—with great weather.”
