Uninhibited and an undisputed “wild child” yet still terminally quaint, Key West is also refreshingly, well, weird, with ghosts haunting its bevy of century-old plantation-style B&Bs, 6-toed cats prowling Hemingway House --even the dead have a sense of humor here, as you’ll discover at Key West Cemetery, where one tombstone from 1979 reads, “I Told You I was Sick.”
So pack your bikini and sunscreen – we’ve got 24 hours of fun, fun, fun to share with you.
7 am: I believe I can fly Book ParaWest’s bargain-priced “Early Bird Special” and go parasailing straight from the foot of the boat, up-up and away 300 feet above the crystalline, emerald-green waters. You don’t have to know how to swim; in fact, you won’t even get wet unless you want to, in which case the pilot can arrange for you to dip your toes in the water upon descent or enjoy a spectacular full-body crash landing.
9 am: Chow down at Blue Heaven An historic and much-beloved local hang (Hemingway refereed boxing matches and customers cheered for cockfights), the shrimp and grits, lobster Benedict with key lime hollandaise and the homemade banana bread and cranberry-orange muffins are to die for while the free-roaming chickens and cats roaming the tree-shaded outdoor patio add that "what-a-hoot" factor.
10:30: Spy on the fishies and catch some rays The snorkeling is stellar at Sand Key Lighthouse, Eastern Dry Rocks and Western Dry Rocks, all located about eight miles southwest of town. Or, for snorkeling nirvana, hop a boat for Key West Snorkeling’s all-day snorkeling adventure in Dry Tortugas National Park, located 70 miles offshore.
High noon at Sloppy Joes: Even if you’re still digesting breakfast, take it from Hemingway and “The Mob” of other literary greats who haunted this historic speak-easy when they needed a break from their typewriters: It’s never too early to start drinking in Key West. Owned by Hemingway’s fishing buddy and BFF, Joe Russell, the speak-easy serves killer conch fritters and the original, if messy, Sloppy Joe sandwich that put them on the map, and can also provide the inspiration you need to scribe a Hemingway-esque short story for January’s upcoming “Flash Fiction Contest.” For the first time this year, the grand prize includes a chance to write, paint, read or do whatever the hell you want (within reason) for 10 days inside Hemingway’s writing studio at the Spanish-colonial estate he called home.
1-2 pm: Bed down with the greats Key West’s hot, sticky afternoons were made for napping under a twirling plantation fan in one of Old Town’s many historic and pedigreed hotels, many painted in crayon colors and sitting atop ingenious 3-foot piers that let the raging winds and waters of Key West’s infamous typhoons pass right through without causing structural damage. If you’re a bad girl, you’ll love the Angelina Guest House, a Hemingway fave that’s a former 1920s bordello and gambling den- turned charming Key West bed-and-breakfast. For you debutante wanna-bes, the gracious Chelsea House is a plantation-style class act where you can savor breakfast on the backyard verandah.
2:15 pm. All hail the Key Lime You simply can’t visit Key West without stopping by Kermit’s Key Lime Shoppe. Kermit proper, a piece of work in his lime-green jacket and chef’s hat, blends in seamlessly with his Key Lime cookies, ice cream, pie-on-a-tick, jams, jellies, jell beans, tea, olive oil, taffy, chutney --you get the drill. Breathless reviews from the Food Network, Nat Geo and Chef Paula Dean have established him as the Key Lime King – and he’ll even give you his granny’s Key Lime Pie recipe.
3 pm The Annual Conch Republic Festival Back in the weed-infused 1980s the Border Patrol erected a roadblock to deter the locals from smuggling marijuana along Key West’s serene maze of secret backwater routes. The locals staged a protest, the Border Patrol relented and today the locals celebrate their victory with an annual fete the last 10 days of April that kicks off with a “drag” race between female impersonators and goes downhill from there with the world’s longest parade (it head won Duval Street and then proceeds from the Atlantic Ocean to the Gulf of Mexico), a pirates’ ball and a bed race billed as “the most fun you can have in bed with your clothes on.” www.conchrepublic.com.
5:30-6 pm: Sunset at Mallory Square As the town where the country runs out of land, Key West is the Sunset Capital of the U.S. which it celebrates with a nightly beach fest featuring a motley crew of street performers, serenading minstrels, and not to forget The Southernmost Bagpiper, Dominique and His Flying House Cats and the legendary “Cookie Lady,” who promotes her warm homemade delicacies while squawking slogans in perfect rhyme. It all happens against a breathtaking backdrop as the sun melts into the sea and blazes the sky pink, purple and orange before surrendering to a canopy of stars.
7 pm: Dinner Latitudes at Sunset Key Catch the tiny ferry to this plantation-style resort located on the private isle of Sunset Key and get ready to feast on the freshest gourmet seafood in town. Try the Crab Stuffed Florida Lobster Tail or “Really Big” Gulf Shrimp and enjoy it with fresh salads and canopies like Portobello Carpaccio and Prosciutto and Sun-dried Tomato Wrapped Brie. As the sunset surrenders to a canopy of stars, order one of each dessert and pass them around the table to taste. The Crème Brulee, Carrot Cake and Dark Chocolate Torte are stunners.
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