A Weekend in Key West

South Florida’s Key West feels a bit like its own island nation, with a tropical climate, plenty of local artists, Victorian-Caribbean architecture and an astonishing population of enormous birds. Situated where the Gulf of Mexico and Atlantic Ocean converge, much of Key West’s bounty comes from the sea — in the form of dinner-to-be, maritime history, water-based activities, ecological splendor and Caribbean breezes. Back onshore, there’s Old Town, the historic area that President Truman and Ernest Hemingway called home. You can do the “window shop Key lime pie on a stick chomp” down well-trodden Duval Street, ducking into art galleries and boutiques, before ending in Mallory Square for a hype-busting sunset. Sure, there’s a lot to do in Key West — and it’s crowded — but take a quick turn down a palm tree-lined street or into an exotic plant-filled courtyard, and you can find … island paradise.

The Perfect Key West Weekend

Day One: Start off on Duval Street, the main drag, and wander the streets of Old Town Key West, popping into a few art galleries for an ogle or a haggle. As you stroll, enjoy Key lime pie dipped in chocolate on a stick or a warm cookie from Mattheessen’s Homemade on Duval. Chuckle (or scowl) at the silly T-shirts displayed in the windows of tacky tourist shops. Drop in for a tour of the Hemingway Home and its five-toed cats. When you realize that all this walking and touring has made you hungry, head off the beaten path a touch and grab a wooden table at Santiago’s Bodega, a small, amiable place serving tapas and a huge selection of wine (reservations are recommended). End the night with live music at the Hog’s Breath Saloon, Sloppy Joe’s, the Bull & Whistle, the Green Parrot Bar, Captain Tony’s or all of the above.

Day Two: Pack a cooler and shoot 30 miles up US-1 to Bahia Honda State Park, stopping on the way for fresh-roasted drink at Baby’s Coffee, an art gallery/coffeehouse located at mile marker 15. Don’t forget to look out both sides of car as you fly northeast up the highway — that’s the Gulf of Mexico on your left, the Atlantic on your right. After a lazy day at Bahia Honda’s beach and a brisk walk along the overseas railway bridge (to the gap and back), it’s time to head back to town. Make a short stop on the return ride for some pizza and beer at the easy-to-miss Keys establishment, the No Name Pub (“A nice place … if you can find it”). Back in Key West, wind your way down to Mallory Square with a locally rolled cigar in hand or mouth in time for the sunset and entertainers. Wait until the crush of cruise ship traffic clears out, plop down at a barstool by the water, and consume a stacked grouper sandwich, lemony oysters and a cold beer.

Day Three: Get out on the water for the first half of the day by chartering a pleasure boat (scenic sail, lunch, snorkel), hiring a captain for some fishing, or exploring the fast-growing mangrove islands and hidden waterways by sea kayak (rent your own or take a guided tour). A decent naturalist will help you spot tarpon, eel, turtles, barracuda, crabs, sharks, starfish and large marine birds (you don’t really need help spotting the giant pelican or egret). A trip out to the Dry Tortugas might allow for you to snorkel a shipwreck, lungs straining to allow a last look at a five-foot-long, 200-pound goliath grouper. If you’re enamored of the water even after you’re back on shore, head to the small but friendly Key West Aquarium to visit some nurse sharks and sea turtles. With Cuba only 90 miles away, celebrate the island’s food at El Siboney, which offers a stacked menu of reasonably priced roast meat dishes, plus paella and sandwiches.

Learn more about this itinerary with our Key West Attractions.

–written by Dan Askin