The island city of Key West, the southernmost point of the continental U.S., has long been associated with a vivacious lifestyle, literary giants Ernest Hemingway and Tennessee Williams, and glorious sunsets.
Key West has not been immune to the natural disasters that have whittled down this part of the country. Having been pummeled by the “Labor Day Hurricane” in 1935 (still considered the worst hurricane to hit the country), the area picked itself up and redefined itself as a destination for chip bars, conch-style houses, and lively nightlife.
After hurricane Irma passed through the area last fall, Key West (along with the rest of the Florida Keys) has rebuilt itself once again—95 percent of all units on the main island and its neighboring Stock Island are back in the game. And with American Airlines' new non-stop service from Dallas Fort Worth (beginning June 9) and increased year-round routes on United (up from seasonal, starting October 4), it is more accessible than ever before. Here's a handy guide for the upcoming season.
When to Go
There are a lot of festivals during the summer months, so planning your visit around these will be the key to having an upbeat (or low-key) time.
June and July are ideal for soaking up Jazz in the Gardens at the lush Gardens Hotel which boasts Bahamian plantation-style furnishings. The colorful Pride festival kicks off on June 6 with five days of beach and pool parties, late-night drag shows, and even a 10k relay for tutu-clad runners.
For live entertainment, the fifth annual Murder Mystery Fest starts on June 22, and the popular Key Lime festival (June 30-July 4) is basically a talent show and a pie-eating contest rolled into one. If you’re a fan of Hemingway, the 38th annual celebration, Hemingway Days, encourages Hemingway look-alikes, writers, and anglers to converge from July 17-22.
Considered the start of shoulder season, August is a much quieter month on Key West. One of the best things to do during this time—other than relax—is indulge in the Brewfest on August 31, when you can sip beautiful craft brews through Labor Day weekend.
Where to Stay
Even though Key West is fairly small in size, it has many lodging choices. With more than 400 hotels packed into a space of 7.24 square miles, it is not hard to find a place that suits you.
If you want to stay in the Historic District, The Marker Waterfront Resort is a good deal for around $250 per night. It’s a short walk to Mallory Square and boasts three pools, so you can soak up the sun in spades. It is the only newly built hotel to open in Old Town in the last 20 years, but it evokes some of the area's bygone glamor in its 96 rooms.
For people watching and views, it doesn’t get better than the Southernmost Beach Resort, which is two blocks from the eponymous landmark (it’s also the closest you’ll come to Cuba in the U.S.). The hotel spans two city blocks and lies on a quiet stretch of the island; rates start at $220 per night.
Heron House is a great adults-only getaway. The cozy rooms and suites feature rattan furniture and brick walls, and it's just minutes from the Hemingway House (rates from $119 per night).
For a truly unique Key West experience, try the The Perry Hotel on Stock Island. This once-sleepy isle north of the mainland morphed into a hot destination overnight when the hotel opened last year. Its 100 nautical-inspired rooms overlook a 220-slip marina and start from $158 per night.
What to See
Despite its diminutive size, Key West is so packed with attractions you'll be hard-pressed to squeeze them all into a single weekend.
The Hemingway Home—still the single largest residential property on the island—is the star attraction. Built in 1851 by Asa Tift, the Spanish Colonial mansion was the primary residence of novelist and war correspondent Ernest Hemingway for more than eight years, and it was the first home on the island to have indoor plumbing. Visitors love it for the polydactyl cats and verdant gardens, as well as the chance to peek into the study where the esteemed writer penned The Snows of Kilimanjaro, among other works. Hemingway fans should also not miss a visit to Sloppy Joe’s—the writer's chief watering hole—on Duval Street.
Sixty-eight miles off the coast of Key West, Dry Tortugas National Park is an amalgamation of seven reef islands, and its coral is among the most pristine in the Florida Keys. As you might expect from the name, there are sea turtles everywhere—the park is home to the most active turtle nesting site in the Keys. Tickets for the roughly two-hour ferry ride are steep—$165 for adults and $125 for kids (roundtrip), plus $15 admission to the park—and should be reserved in advance.
The Audubon House off of Duval Street is a resplendent armory of period architecture and is known for its tropical gardens. A great place for selfies is the Southernmost Point, which boasts hawkers and souvenir peddlers.
And finally, a visit to Key West just wouldn’t be the same without taking in a lovely sunset at Mallory Square, over a cocktail or two.