Fort Zachary, Key West
At the leisurely pace of a beach-cruiser, clients can best experience the active, but low-key feel of Key West. Alcohol is as enjoyed in the tropical island as fresh seafood and key-lime pie, but mainly by retired folk drunk on the inspiration of past residents Ernest Hemingway and Tennessee Williams. While famous for being only “90 miles to Cuba,” the southernmost tip of the Florida Keys offers clients at least five different reasons to stay on American soil:
Ernest Hemingway Home & Museum
Ernest Hemingway Home & Museum
Checking off classics in the “must-read-before-I-die” list is a classic vacation activity made easy in Key West, where Ernest Hemingway’s presence is felt even at the beaches. A must-see in Old Town, The Ernest Hemingway Home and Museum is the site in which the Nobel and Pulitzer Prize winner wrote 70 percent of his work, including For Whom the Bell Tolls
and his only novel set in America— To Have and Have Not
, which takes place in depression-era Key West. His intact writing studio is not the only room worth seeing, as the Spanish Colonial style home contains Key West’s first pool and much of the exotic furniture — chandeliers, head boards, and benches — that Hemingway’s second wife Pauline imported from Spain, Italy, and Portugal during their stay in the 1930s. Fans of the author — such as those who flock to the island during July’s annual Hemingway Days festival to participate in inspired activities like deep sea Marlin fishing and a three day look-alike contest — will be happy to know that “Papa” is kept alive by a throng of cats descended from the author’s own polydactyl cat and a knowledgeable cast of look-alike tour guides.
Rick’s Downstairs & Rick’s Upstairs Bars
Rick’s/Durty Harry’s Entertainment Complex is comprised of eight venues and 12 bars, but a balanced combination of Rick’s Downstairs bar and Rick’s Upstairs bar is the perfect recipe for a great night. Rick’s Downstairs offers cheap drinks and the chance to prove the potency of said drinks with free karaoke, while Rick’s Upstairs — complete with a DJ, a 1,500 square foot dance floor, balconies, and a ring of bars — is one of Key West’s only spots to dance to top 40 hits. For those left teased by the nude bar across Duval Street called Garden of Eden, Rick’s Red Garter Saloon offers free entry to its adult entertainment.
Dante’s of Key West
Dante's Po Boys
“Yes, I’m on the seafood diet,” the clever person smirks. “When I see food, I eat it!” In Key West, where restaurants boast fresh and locally caught oysters, lobsters, shrimp, and other fish, seafood/see food is more of a synonym than a pun. The overflow of fresh fish is best captured by Dante’s “Po Boys” sandwich, which is as enjoyable to watch get eaten as it is to eat. Your choice of oysters, shrimp, or conch is grilled with dill havarti cheese, slaw, and Cajun tartar sauce on Cuban bread and served with sweet potato fries. The size of the average human being’s face, the sandwich compensates for the hunger felt after a long day sunbathing or playing water sports at Smathers or Fort Zachary Taylor Beach. Like other local favorites — Pepe’s, which always feels like brunch time on an extended porch, and BO’s Fish Wagon, which is shabby shack chic at best — Dante’s is outdoors and complete with a bar. Unlike its competitors, Dante’s offers a pool for patrons to enjoy until dusk. Some words of advice to pass onto clients: Only swim before Dante’s drinks and meals.
Sloppy Joe’s Bar
You never know who will be getting sloppy at Sloppy Joes, or when. Far from a subdued, scholarly pub, Sloppy Joe’s is always the busiest bar on Duval Street. The bar is named after Hemingway’s favorite Key West watering hole, which has since been renamed Capt. Tony’s Saloon. Proud of its legacy, Sloppy Joe’s is decorated with portraits of Hemingway and his look-alikes and recently hosted the 29th annual Papa look-alike contest. A great place to start, end, or spend the night, Sloppy Joe’s is open from 9 AM to 4 AM, with patrons dancing to live rock music at noon and at night.
Sunset Celebration at Mallory Square
Performers at Mallory Square
Wrecking — taking valuables from shipwrecks — used to be a thriving industry in Key West in the 19th century. The center of wrecking activities, Mallory Square now brings together a rich collection of performers, artists, musicians, and food vendors each night. Clients can enjoy the art of the island vendors, or simply be inspired by the unobstructed view of the sun setting over the Gulf of Mexico.