A chain of islands surrounded by the waters of the Atlantic Ocean, Key West is a world apart from the mainland. The southernmost city in the continental United States, the sun-soaked outpost treats visitors to a seamless blend of nature, nightlife, and history. Of course, it’s easy to assume the place is little more than a three-mile-long bar — and that’s not entirely untrue. But, beyond the buzz of Duval Street and the side streets full of endless-happy-hour spots, there’s more to see in this island paradise than most visitors ever consider. The town has famously been home to literary giants including Ernest Hemingway, Tennessee Williams, Robert Frost, and Elizabeth Bishop. Of course, the tropical outpost was also the longtime home of Jimmy Buffet, who has regularly paid musical homage to Key West in his songs.
Today, 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.
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When to Visit the Florida Keys
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 comfortable with a 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 there are fewer tourists.
With a long list of events 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 showcases 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 in 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 at Fort Zachary Taylor State Park and Key West harbor to watch more 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 premieres as well. It’s a full-featured event with a huge kick-off party, exclusive screenings, and an awards gala.
Where to Stay
In terms of overnight accommodations, Key West has something for everyone. There are hotels, Airbnb’s, and mom-and-pop places such as you might see on the series Bloodline for rent in Key West. Thing is, there’s only so much real estate, as anyone who visits can tell you, it can be expensive. Book your lodging far in advance of your trip to get the best rate.
Eden House
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.
- Nearest Airport: Key West International Airport
- Time: 14 minutes
- Distance: 4.9 miles
Southernmost Beach Resort
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.
- Nearest Airport: Key West International Airport
- Time: 14 minutes
- Distance: 4.8 miles
The Gardens Hotel
A Key West mainstay since the 1800s, the property that is now known as The Gardens Hotel was once slated to become a botanical garden. In 1930, masterful landscaper Peggy Mills purchased the estate, and transformed the property into an exquisitely lush garden, with exotic tropical plants and artfully-crafted brick walkways. And, the tranquil vibe remains, although these days, the property even has amenities for guests, including heated pools bicycle rentals, and the well-stocked Wine Gallery. Accommodation options include airy guest rooms, an artfully-appointed master suite, and five distinctive cottages, four of which include private pools.
- Nearest Airport: Key West International Airport
- Time: 10 minutes
- Distance: 3.6 miles
What to Eat and Drink
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 Magaritaville, 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. Thankfully, Key West’s diminutive size hasn’t stopped the proliferation of amazing restaurants on almost every corner of the island.
- “$” = budget-friendly or cheap
- “$$”= average
- “$$$”= expensive
Santiago’s Bodega
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 décor 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 house-made sparking sangria. Reservations are highly recommended any time of day as it’s just we popular with locals as with tourists.
- Best for lunch, dinner
- $$
Garbo’s Grill
For something a little more ‘grab-and-go,’ check out Garbo’s Grill. This husband-and-wife owned food truck behind Grunts Bar serves up simple but creative takes on handheld foods like burgers, burritos, and tacos. The tiny, palm-lined patio is a chill, cozy place to dine alfresco.
- Best for lunch, dinner
- $$
Better Than Sex
If you can forgive the ham-handed, Valentine’s Day schtick 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.
Green Parrot Bar & Charlie Mac’s
The Green Parrot Bar claims to be the oldest bar on the island. Rumors abound in support of and against the claim. Either way, they’re 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 on the 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 and schnapps with a chaser of their cheapest beer.
- Best for drinks, lunch, dinner
- $$
Captain Tony’s Saloon
A quintessential dive bar, the property housing Captain Tony’s Saloon as served a lot of functions – and featured prominently in local lore, even earning a mention in Jimmy Buffet’s song Last Mango in Paris. Originally constructed in 1851 as an icehouse that also operated as the local morgue, the property housing Captain Tony’s Saloon served a lot of functions before first being opened as a bar in 1933 – a spot known as Sloppy Joes, famed for hosting the likes of Ernest Hemingway on a regular basis. But, after a dispute with the landlord, Sloppy Joes moved to Duval Street in 1938 – and two decades later, local charter captain Tony Tarracino bought the joint, and the rest is history.
Salute! on the Beach
To escape the maddening crowds, Salute! on the Beach offers decidedly relaxed cocktails and dining far from Duval Street. Hop an Uber to this funky hangout situated directly on the sand at Higgs Beach where beachgoers have easy access to clear tropical cocktails and seafood-centric snacks.
- Best for lunch, dinner
- $$
Key West Legal Rum
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 brulée rum.
Blue Heaven
For such a tiny island, the breakfast options are surprisingly plentiful. But, even locals agree nothing touches Blue Heaven. The rustic sister restaurant of Salute! has an al fresco 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 BLT Eggs Benedict with fresh Florida lobster, bacon, avocado, and lime hollandaise sauce. Follow it with a slice of scratch-made key lime pie (because pie with breakfast is acceptable here) – key lime juice and rich graham cracker crust, topped with six full inches of meringue.
What to Do
Exploring the beaches and swimming in the turquoise water of the Keys should be at the top of every visitor’s list. Whether you do this by snorkeling, scuba diving, or riding a jet ski is up to you. Of course, the rich history of Key West is worth diving into as well. Additionally, Key West sunsets are not to be missed, as street performers offer lively entertainment while you stroll the streets, enjoying the breeze. The island definitely toes the line between ‘Jimmy Buffet-inspired touristy’ and ‘chic island bohemian.’ When you’ve had your fill of the bustle of Duval and half-drunk-by-morning tourists, escape to Key West’s best off-island experiences. What you may not know is that 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
Home to the storied author from 1931 to 1940, Hemingway House is a requisite first stop for new visitors as it provides the perfect primer. After moving into the Spanish colonial house with his second wife, journalist Pauline Pfeifer), Hemingway penned works including Green Hills of Africa (1935) and The Short Happy Life of Frances Macomber (1936) at the property. 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.
Barefoot Billy’s (Water Adventures)
Not surprisingly, Key West’s best adventurous diversions are on the ocean. Barefoot Billy’s offer 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.
Dry Tortugas National Park
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 floatplanes 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.
Sunset Key
Even with the 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. After sunset, head to Latitudes – the hotel’s beachfront restaurant, routinely ranked about the best and most romantic in Key West.
Key West Cemetery
Nestled into Old Town, the Key West Cemetery is a microcosm of local history. Established in 1847, the 19-acre cemetery is the final resting place for locals from all walks of life, from mariners to cigar makers to millionaires. Maps of the cemetery are available from the Sexton’s Office for self-guided tours, and the Historic Florida Keys Foundation also offers walking tours twice a week. Of course, with a reputation as one of the most haunted places in town, the storied cemetery is also one of the stops showcased on the Ghosts & Gravestones Tour of Key West.
How to Save Money on Your Trip to the Keys
Experiences
Look for Groupon deals, discounts through your hotel, and savings for those shopping online. And, don’t forget about Key West’s budget-friendly experiences, from free, self-guided walking tours to historic sites to public beaches.
Hotels
While the weather can be unpredictable during the hurricane season in late summer and early fall (typically in September and October), there are ‘off-season’ accommodation rates available. And, if possible, book in advance to snap up the best deals.
Vehicle Rentals
Book in Advance and be open to whatever is available. Rental cars can be expensive right now and having some flexibility will help you save money.
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