Ask a Local About Key West, Florida

Whatever your pleasure—swimming, snorkeling, fishing or boating—locals suggest you take a break from revelling on Duval Street and hit the water. Key West has the longest (and third largest) barrier reef in the world, mangrove forests teeming with wildlife, and a coastal tour for every taste. The Spirit of Independence is an old schooner that sails at sunset, wining and dining with icy pinot grigio, sophisticated sandwiches, and assorted delicacies from Duetto’s restaurant. For a low-key—and lower-priced—option, there’s the Schooner Jolly II Rover, which is BYOB and fun for the whole fam: kids will go crazy when the ship’s crew fires its cannons at passing boats (don’t worry, it’s fake). Or, if you’re up for getting wet, locals love exploring the island’s coastal mangroves by kayak or stand-up paddleboard. Try Key West Eco Tours for gear and a guide.

“The place for Key Lime Pie,” according to locals, Blue Heaven is a quirky Key West institution and not to be missed—unless its free spirit owners have hung up their “gone fishing” sign and closed shop for the day, as they’re occasionally known to do. With a rooster graveyard (!!!) and an old sail strung between trees for shade from the tropical sun, this sprawling backyard restaurant-bar-live music venue is as casual as they come. But don’t be fooled; Blue Heaven is serious about its food. Whatever else you order—and everything here is great—follow it up with the island’s namesake pie, which is sweet and tart and piled with a mountain of baked meringue. For classic no-fuss Cuban food, locals say El Siboney is “hands down” the best around. The discrete half-century-old restaurant is easy to miss if you’re not looking, but you won’t want to pass by their downhome Cuban grub. Locals recommend “anything on special” and the #1: puerco asado, or roasted pork. “They kill it on food,” we’re told. And if fresh fish is your passion, head to the nautically-themed Little Pearl and order the local swordfish, grouper, or Bahamian conch chowder. Incredible!

Just four miles long and a mile wide, Key West has been home to a fascinating assortment of characters and events. For a (free!) do-it-yourself history lesson, follow the Pelican Path self-guided tour and visit the former homes of writer Ralph Ellison, Ernest Hemingway, and President Harry Truman whose “Little White House”is now a museum. If you want to dig a little deeper, take a stroll with the Key West Art and Historical Society and learn about the island’s weird and wonderful past from professional historians who focus on single subjects like “Key West Writers and Artists” and the naval history of the Truman Annex. There will be plenty of pirate stories...

Locals boast that Key West has more bars per capita than anywhere in the world. It’s not surprising, then, that the island hosts a booze hall for every taste and sensibility. At Mary Ellen's, a neighborhood bar where the bartenders hang out when they’re not slinging for tourists, there are drag (queen) races and gourmet grilled cheese sandwiches. At the Saint Hotel’s Pilar Bar, the ordinary Bloody Mary is transformed into “The Almighty”—a buffet of garnishes that includes an entire piece of Yorkshire pudding and a prime rib parcel with homemade horseradish cream. The oldest bar in Key West, the Green Parrot, is a beloved dive with a pool table and free popcorn (because it’s the little things that keep a bar going for 128 years). But newcomers to the scene offer their own appeal. Tucked away above the well-known Louie’s Backyard, the Café at Louie’s is wonderful little wine bar serving small plates like scallop ceviche with baby heirloom tomatoes and citrus sections that “no one seems to know about”—and who doesn’t love to be in on a secret?

Much of Key West’s charm lies in its back streets, odd little nooks, and hidden spots waiting to be stumbled upon. But even locals see the attraction of Duval Street and its raucous, good-time vibes and Mallory Square, where sunsets are a two-hour circus nearly every night of the year. With street performers and surprisingly talented musicians vying for your busking dollar, vendors selling conch fritters and cocktails, the scene is lively and festive. But that’s not the full spectacle! Look for the Green Flash Effect, where on “magical nights” the sky flashes green just as the sun dips into the ocean.

South Florida is all about the beaches and the best stretch of sand on Key West, according to locals, is Fort Zachary Taylor. It’s a little rocky, and it costs a couple bucks to get in, but those characteristics translate to smaller crowds and good snorkeling right offshore. No boat required. “You almost feel like you're on a deserted island.”