Go West, Young Man–to Key West, South Florida’s Shining Star

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It’s easy to assume Key West is little more than a three-mile long bar. That’s not entirely untrue. But, beyond Duval Street and the side streets full of endless-happy-hour bars, there’s more to see in this incredible island paradise than most visitors ever consider. Locals appreciate the eccentric, the artistic, the bohemian, and celebrate anyone or anything that’s just a little weird. Here’s a guide to traveling the United States’ southernmost outpost like a proudly off-kilter local.

Must-do

Start at the Beginning

The island’s modern history is inextricably linked to the life of Ernest Hemingway. To understand and fully appreciate Key West, you must start at the beginning. Hemingway House is a requisite first stop for new visitors as it provides the perfect primer. A tour of the museum takes little more than an hour or two. Guides provide a light, educational glimpse into the life of not just Hemingway the man, but the history of Key West as a whole. Much of his original memorabilia (including a tiny writer’s loft which appears frozen in time) and plenty of six-toed cats still remain.

Learn the Best Ways to Get Wet

Not surprisingly, Key West’s best adventurous diversions are on the ocean. Barefoot Billy’s offers a host of guided water-based activities including snorkeling, dolphin watching, and harbor cruises. But their big get is a two-hour Jet Ski tour that circumnavigates the entire island (no previous skill required). While there are a handful of stops along the way, the tour is fast so be prepared to keep up.

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If that isn’t disco enough, the Jetpack Adventure from Cool Key West is something altogether different. Properly outfitted with a water-powered Jetlev R200 Jet Pack, riders can literally fly Iron Man-style up to 30 feet over Key West Harbor for 30 minutes at a time.

Eat Up

Key West’s diminutive size hasn’t stopped the proliferation of amazing restaurants on almost every corner of the island. Santiago’s Bodega may look a little too low-key but, once inside, it’s impossible not to appreciate the Spanish-meets-Keys charm of this tiny tapas bar. The decor is quaint and understated, especially given the out-of-this-world good small plates that are the best in Key West (and arguably the state). Virtually everything on the menu pairs well with a pitcher of their housemade sparkling sangria. Reservations are highly recommended any time of day as it’s just as popular with locals as with tourists.

For something a little more “grab-and-go,” check out Garbo’s Grill. This husband-and-wife-owned food truck behind Grunts Bar serves up simple, but creative takes on handheld foods like burgers, burritos, and tacos. The tiny, palm-lined patio is a chill, cozy place to dine alfresco.

If you can forgive the ham-handed, Valentine’s Day shtick theme of Better Than Sex, you’ll be in for some of the island’s best after-dinner treats. This dimly lit dessert bar provides no illusions about its menu and every plate is almost unnecessarily decadent. Opt for the original Better Than Sex — dark chocolate-soaked pumpernickel bread pudding filled with rich sweet cherries.

Crawl the Pubs Wisely

Duval Street offers the highest concentration of bars and pubs on the island. It’s the de facto center of Key West’s nightlife, but also its biggest tourist draw.

Start your crawl just off the strip near the Mile Marker 0 sign at Green Parrot Bar which claims to be the oldest bar on the island. Rumors abound in support of and against that claim. Either way, they’ve been slinging stiff drinks since 1890 and it feels as though the place has hardly seen a cleaning since. It’s a textbook example of what a dive bar should be: plenty of live music, attitude, and no food menu (try the BBQ at Charlie Mac’s next door if you’re hungry). Don’t miss their Root Beer Barrel — the house boilermaker that combines root beer schnapps with a chaser of their cheapest beer.

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The Smokey Burger at Charlie Mac’s

Four blocks away lies The Porch — a modern wine and craft beer bar in a beautiful 1839 Victorian mansion that provides a stark contrast to “The Parrot.” Funky island-inspired artwork surrounds the relaxed bar area where the ever-changing craft beer menu includes 18 taps and 50 more bottled varieties, plus 70 wines by the bottle.

To escape the maddening crowds, SALUTE! on the Beach offers decidedly relaxed cocktails and dining far from Duval Street. Hop an Uber to this funky hangout situated directly on the sand at Higgs Beach where beachgoers have easy access to clever tropical cocktails and seafood-centric snacks.

Key West Legal Rum is an ideal end point for an afternoon pub crawl. The chef-owned distillery embraces the island’s long, sordid history with liquor and prohibition. The tasting room provides plenty of history along with free samples and bespoke rum-centric cocktails. While the menu changes often, ask about the Green Flash — a unique blend of lightly carbonated ginger, lime, demerara sugar, and vanilla brûlée rum.

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Pier at Key West Florida

Nurse Your Hangover

For such a tiny island, the breakfast options are surprisingly plentiful. But, even locals agree that nothing touches Blue Heaven. This rustic sister restaurant of SALUTE! has an alfresco courtyard where roosters run wild beneath the tables. It’s a staple of the island’s breakfast scene and the wait can sometimes be more than an hour. But it’s well worth it because every last thing on the menu is creative and amazing. We recommend their BLT Eggs Benedict with fresh Florida lobster, bacon, avocado, and lime hollandaise sauce. Follow it with a slice of scratch key lime pie (because pie with breakfast is acceptable here) — a perfectly dense concoction with pure key lime juice and a rich graham cracker crust, topped with a full six inches of meringue.

Plan Your Escape

The island walks a fine line between “Jimmy Buffet-inspired touristy” and “chic island bohemian.” When you’ve had your fill of Duval Street and half-drunk-by-morning tourists, escape to Key West’s best off-island experiences.

Seventy miles west, you’ll find one of the most unique national parks in the United States. Dry Tortugas National Park is a stunning, remote outpost that few Americans have ever heard of, let alone visited.  It’s comprised of seven islands, protected coral reefs, and Fort Jefferson — a sprawling, 19th-century military installation that saw little use in its day and still remains very well-preserved. The real win for travelers is just off-shore as the island is home to some of the clearest, warmest tropical waters in the country. Chartered float planes are the fastest (and most expensive) means of transportation to/from Key West, while the ferry is far slower but allows you to take in the scenery. For an “all-in” experience, the park service offers limited overnight camping for no more than a dozen visitors. But, be prepared: there are no services (water, cell service, or electricity) of any kind. You are, quite literally, on your own.

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Fort Jefferson in Dry Tortugas National Park

Even with miles of stunning coastline, The Florida Keys are not known for their Caribbean-style, soft sand beaches. For a rare beach experience in Key West, book a day pass to Sunset Key, just a seven-minute boat ride across from Mallory Square. The tiny island is home to one of Florida’s most exclusive hotels and a limited number of non-guests are allowed to relax on its private, flour-soft beach each day. With only a few dozen passes available daily, it’s easy to carve out a patch of sand all to yourself. After sunset, head to Latitudes — the hotel’s beachfront restaurant that’s routinely ranked among the best and most romantic in Key West.

Where to Stay

For locally flavored accommodations, it’s hard to beat Eden House. It was Key West’s first hotel and, even after several renovations, it retains the island’s charming, bohemian-meets-Colonial vibe. It’s “boutique” in every sense of the word — the sort of place where check-in beers are complimentary and every guest is guaranteed a hammock.

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Beachfront lodging is scarce in Key West, but Southernmost Beach Resort is an exception. The Colonial-style cottages are chic, upscale, and offer plenty of island flare — all spread across six beachfront acres overlooking the Atlantic Ocean. What’s more: it’s within a short walk to the action on and off Duval Street, but far enough removed to assure plenty of quiet and seclusion.

What to Skip

At just seven square miles, Key West is tiny. So, thankfully, its tourist district is condensed into a single road — Duval Street. It’s home to Starbucks, Denny’s, Jimmy Buffet’s Margaritaville, mass-produced tchotchke shops, and pop-up stands with buckets of booze always on “special.” It’s worth the stop because you can’t fully appreciate modern day Key West without it. But, the best parts of the island are found on the many side streets and alleys off Duval.

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Duval Street

Pack Your Bags (When to Go)

Now that you know what to do, the only thing to decide is when to go. Springtime (between March and May) is the ideal time to visit. Crowds begin to thin out from the winter rush, but the weather is still in the comfortable, 70- to 80-degree sweet spot. Winter is the high season as those from the Northern U.S. hurry to escape the cold. Summer is a gamble as it brings hurricane season (June to November) which is humid and often rainy, but hotels offer great rates and few tourists.  

With a long list of events in every month of the year, Key West is a festival lover’s dream. Here are the highlights:

  • January: The five-day Key West Food & Wine Festival is a culmination of 30 events to celebrate the island’s unique Floridian-Caribbean cuisine.
  • April: The Cow Key Channel Bridge Run isn’t a major event. But, as “the only zero K bridge run,” it perfectly embodies Key West’s eclectic, funny, and just plain weird culture. April also brings the annual Conch Republic Independence Celebration which celebrates Key West’s historic and bizarre 1982 “secession” from the United States.
  • June: Like a toned-down version of Fantasy Fest, Key West Pride is a multi-day event to promote the One Human Family philosophy so thoroughly engrained into the island’s way of life.
  • October: Fantasy Fest is Key West’s 10-day Carnival and the one can’t-miss annual event. It’s loud, wild, and very close to a bacchanal where (almost) anything goes. Make your travel plans early and be prepared to pay a hefty premium for hotels and just about everything else.
  • November: For almost four decades, the Super Boat Annual Key West World Championship has been one of the world’s premier powerboat racing events. Spectators crowd Fort Zachary Taylor State Park and Key West harbor to watch the top contenders race at more than 100 mph. The following week sees the Key West Film Festival which features the best in independent cinema for offbeat foreign, LGBT, and documentary films, plus Florida-centric movie premiers as well. It’s a full-featured event with a huge kick-off party, exclusive screenings, and an awards gala.