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10 Reasons to Love Key West: Key-easy living, she-crab soup and cold beer all day long

Ah, Key West - birthplace of the languorous afternoon, long-winded fishing tale and late-afternoon boat drink. Just a stone’s throw from Cuba, this sultry island outpost has inspired loyalty in the hardest of hearts and fiction from some of the world’s most legendary pens. Sitting pretty at the tail end of the East Coast, Key West is long on winning attributes and short on detractors. Fly into one of the many South Florida gateways, rent that convertible you’ve always pined after and steer your way down through the mile markers to the place that gave laziness a good name.
  • If you opt to go the rental car route, make a pit stop at Mrs. Mac’s Kitchen at mile marker 99.4 in Key Largo to appropriately acclimate yourself to your honorary Key-easy lifestyle. One of South Florida’s great greasy spoons, Mrs. Mac’s serves breakfast all day and draws locals and returning regulars with its license-plate decor, Sloppy Joes and cold beer all day long.

  • Many a valuable lesson has been learned on the open sea. Eat your fruit (lest you end up with scurvy), work cooperatively (lest you end up sailing in a circle) and keep your eyes open to the wonders around you (lest you miss out on the sea-cucumber encampment off the starboard side). While you may never experience the former, you will most certainly rub elbows with the latter when you sign up for an eco-paddle with Blue Planet Kayak. Get hands-on with the region’s most squishy sea hares and spiny starfish under the guidance of resident naturalists ready to point out a jellyfish at 20 paces and steer you though stands of mangroves into hurricane holes just big enough to shelter a dingy.

  • One of the great delights of Southern cuisine can be found here in endless variation. She-crab soup, that otherworldly concoction named for the female crustacean that supplies the orange roe that gives it that special zip, shows up on almost every menu on the island with the personality of each kitchen shining through. For an afternoon you’ll never forget, find a ramshackle eatery on a marina that serves up frosty boat drinks, conch fritters and she-crab soup. Load up the jukebox and spend the afternoon spinning stories, singing songs and watching the day’s catch come in off the charter boats.

  • Perched like a blue beacon at the edge of the marina, the resident parrot at the Hyatt Key West swings lazily on his rope perch, eyes fixed on the horizon. While resident wildlife may not be what you would expect from a chain hotel, the Hyatt Resort & Marina is no ordinary link in the chain. One of the island’s most simultaneously chic yet laid-back properties, the Hyatt boasts contemporary island style and hip guest rooms you'll be hard pressed to leave. Don’t miss out on sunset cocktails at the Blue Mojito Pool Bar & Grill, key lime amenities in the showers and the indulgent Jala treatments in the newly opened Jala Spa.

  • Book a snorkeling trip, champagne sunset cruise or private charter on the Floridays yacht and spend a few hours hobnobbing like a jet setter. While you’re out there, strap on a set of flippers and snorkel your way around the star-shaped reef. Keep your head down and your eyes open for face-to-face encounters with nurse sharks, parrotfish and not-to-be-touched fire coral.

  • Back on dry land, rent a bike from Paradise Rentals on Fitzpatrick Street and peddle down Duval for a little fresh air and window-shopping. Hang a right on Southard and stop for a coffee at Island Joe's Coffee Roasting Company.

  • From late-December through mid-March, locals swing the gates of their guarded estates wide for the Key West House and Garden Tour. A true behind-the-bougainvillea look at Key West, the tour is put on by the Old Island Restoration Foundation and gives visitors an inside peek at how long-time locals have restored and redecorated the island’s historic homes. Buy your tickets early from Key West’s Oldest House & Garden at 322 Duval Street, or at the featured homes during tour hours, and come prepared to gawk.

  • Billy Crystal and Gregory Hines made a witty team as two Chicago cops who opted for the ultimate lifestyle adjustment in 1986’s Running Scared. Their discovery that ending the day by watching the sun set beat the pants off chasing homicides under the “El” made many a Northerner reconsider his retirement plans. Every day, tourists and locals alike set aside a few minutes to take in the fiery glow of Mother Nature’s last stand. A stroll down to Mallory Plaza still offers unparalleled views and even better people watching.

  • Key West is nothing if not festive. Residents may take pride in the Key-easy lifestyle, but they never miss an opportunity to turn the volume to 11 for any of the islands annual festivals. If you like it bawdy, show up on the last week in October for the annual Fantasy Fest, a 10-day free-for-all of balls, costume competitions, AIDS fundraisers, body painting, drag queens in full regalia and one heck of an over-the-top parade. Think of it as a gay-friendly Mardi Gras with fewer frat boys.

  • Papa don’t live here anymore, but that doesn’t stop locals and out-of-towners from flocking to honor Hemmingway himself through Sloppy Joe’s annual Papa Look-Alike Contest. Hirsute wannabes from coast to coast converge on this ramshackle street-side bar to settle the similarity score for one more year.

    This winter, if you find yourself desperate for a break from slushy sidewalks and winter’s ever-present grayness, point your compass as far south as the roads will take you. Disappear for a long weekend to the place where it’s summer all year long and the sun never sets on the laid-back good times.


Sarah Reiss a full-time travel writer, SATW member and contributing travel editor. Her column, The Thoughtful Traveler, appears quarterly in 11 East Coast newspapers, and her monthly column, 10 Reasons to Love..., runs on OffbeatTravel.com. When she is not on the road, she calls the mountains of Southern California, where she lives with her husband and two dogs, home. SarahReiss.net