The No. 1 reason people come to Key West is to have fun-it’s as simple as that. T-shirts, shorts and a pair of flip-flops will do. Key West’s nickname, the Conch Republic, has a comedic ring to it, hinting that this island is a place where almost anything goes (including a possible succession from the union in 1982). So get ready for some serious fun. You’re on island time now.
1 Old Town
The bustling Old Town is a national historic district, with Victorian charm and tropical gardens. A grid of narrow streets with homes from the 1800s and a mix of cultures from the Bahamas, Cuba, Europe and the Eastern Seaboard give it its intriguing history. Three places worth visiting are Mel Fisher Maritime Museum, President Harry S. Truman Little White House and Ernest Hemingway Home & Museum. Or, heck, just find a bar and chill.
2 Two-Wheel Paradise
You’ll get your share of exercise in this town, but not on two feet. Take your pick from a rental bicycle or scooter and ride with the wind in your hair as you exploring the island on a cool set of wheels. Just watch out for the chickens crossing the road.
3 Sunset Hour
Nowhere else in Florida is the setting of the sun celebrated with so much fanfare as in Key West. Mallory Square on the Gulf of Mexico is where tightrope walkers, fire eaters and jugglers entertain, and vendors with carts of local artwork and beaded jewelry hawk their wares. The shoulder-to-shoulder crowd may be toasting the end of a good day on Key West, but as the fire ball slips below the horizon, the party’s really just beginning.
4 On and Under the Water
There’s no limit to the choices for getting out into the Atlantic Ocean or Gulf of Mexico. Start at the Historic Seaport at Key West Bight and take your pick. Adventurers find dolphin-and-shipwreck snorkel trips on catamarans and snorkel trips to the reef by kayak. Fishermen can book charters—deep sea fishing, flats fishing or light tackle trips. The leisure traveler has several sunset sails from which to choose—we opt for the champagne sunset cruise.
5 Duval Street
Key West’s main drag, Duval Street, runs from bayside on the Gulf of Mexico to ocean side on the Atlantic, and you can easily walk the entire stretch. It’s the heartbeat of Key West. During the day it’s a shoppers’ and early-bird drinkers’ street, at dusk it welcomes diners and the five o’clock somewhere crowd and by dark it turns into a serious party scene.
6 Duval Crawl
Bars and drinking go hand in hand, a Key West tradition that one might say began with Ernest Hemingway at Sloppy Joe’s, the author’s favorite bar back in the 1930s. Only today there are more bars and more people doing the “Duval Crawl.” Whether you join the official Duval Crawl event to hit the watering holes or do your own freestyle crawl, drinking and making friends is what happens nightly on Duval Street.
The catch of the day is always fresh and plucked from surrounding waters. The local hogfish makes a killer fish sandwich, the grilled Key West pink shrimp get a thumbs-up and a basket of conch fritters is a must.
There’s never a shortage of events going on in Key West. But the big ones you need to book in advance are July’s Hemingway Days, with its Ernest Hemingway look-a-like contest; and October’s Fantasy Fest, a wild 10 days of outrageous costumes, parades, parties and borderline mayhem.
9 Hop On, Hop Off
Tired tootsies? Short on time? The Old Town Trolley to the rescue. This is the easiest way to take in as much of the island as possible—or just get the lay of the land. The ding-dong of the trolley is heard all over the island as it makes its way to 12 stops from Mallory Square to the Southernmost Point of the Continental U.S.
10 Stay the Night
Key West boasts some of the most interesting innkeepers, who run the bed-and-breakfasts, inns and guesthouses. Besides maintaining the architecture and history of these buildings—a ship captain’s home, a Caribbean cottage, a Victorian mansion—they make sure laughter accompanies your stay with daily happy hours.