Key West and the Florida Keys

While the weather is warm year-round, the best time to visit the Florida Keys is during the dry season, between November and April. That, of course, is also the high season, so room rates will be high. If you’re looking for fewer people, days that aren’t too hot, and decent hotel availability, visit between the rush of spring break and late May. The hurricane season runs from June through November, but the for those in the mood to gamble, those humid months also bring the best room rates.

If you choose to drive (and unless your ultimate destination is Key West, you undoubtedly will), you’ll find yourself driving along the Overseas Highway and its 42 bridges. Domestic and international airlines offer flights to Miami International Airport, but you can also fly directly into Key West International Airport on a number of domestic airlines (Delta, United, American, and Silver Airways). Another way to get to Key West is via ferry from Fort Myers or Marco Island on Florida’s Gulf coast. Key West is only a 2-by-4-mile island, so if you’re staying here, you can skip driving and get around on foot, bike, or scooter.

All along the archipelago, the nightly sunset is cause for celebration. In Key West, crowds gather at Mallory Square to boisterously bear witness to the sun’s descent into the Gulf. Other destinations in the Keys celebrate more quietly, but cocktails are almost always involved.

Fishing is still a vital part of the Keys culture. Even if you don’t want to drop a hook, try to get out on the water while you’re visiting, and do your best to keep the local commercial fishing ventures afloat by indulging in as much fresh seafood as you can. Conch, anyone?

Key West is closer to Cuba than it is to Miami, and this geographical blessing shines through in its culture and cuisine. To honor that connection, make your way to the iconic Southernmost Point marker that marks 90 miles to Cuba.

First-time visitors shouldn’t miss the home of one of Key West’s most celebrated residents—the Ernest Hemingway Home and Museum. The Old Town house looks exactly how it did when the writer resided in the Conch Republic, and descendants of his six-toed cat Snowball still roam the grounds.

You’ll find a wealth of fresh seafood on the region’s menus—especially stone crab, lobster, fish, and conch. On the northern end of the island chain, cuisine often takes a Caribbean turn with coconut and mango making plate appearances (and showing up in cocktails, too). The food in Key West shows a distinctly Cuban influence, especially at breakfast when a cup of cafecito and some toasted bread will soothe the lingering headache from last night.

The Keys dining experience wouldn’t be complete without key lime pie. In Key Largo, Mrs. Mac’s Kitchen serves up a popular slice, and Islamorada’s Green Turtle Inn has diehard fans. In Key West, several shops claim to serve the best one in town (some with mile-high meringue, others with a modest dollop of whipped cream), so you should conduct a scientific test and decide for yourself.

Chances are, you won’t be thinking about museums while sunning on the beaches and lagoons of South Florida, but the region *is* a magnet for fine artists and writers, so you may inadvertently be exposed to some culture. Music—and not just the works Jimmy Buffett, (though, goodness knows, you’re likely to hear a few verses of Margaritaville during your visit) —has a way of inserting itself into the daily Keys experience.

The region’s position at the edge of the continent means history, too—in the forms of crumbling military installations to be explored and lots of pirate lore. Key West’s Mel Fisher Maritime Museum holds the artifacts salvaged from shipwrecks off the Keys, including vessels carrying Africans bound for slavery, as well as booty from a pair of 17th-century Spanish galleons.

Key West’s Mardi Gras atmosphere permeates the island year-round and can be experienced on any given day by heading into one of the Old Town bars or by attending the Sunset Celebration along with sword-swallowers and fire-jugglers. The town also has its fair share of literary haunts and a visit to the Ernest Hemingway Home & Museum and the tiny Tennessee Williams Exhibit will make you feel part of the scene.

Lane Nieset