Off the southernmost coast of Florida sits Key West, a small island whose slogan may as well be: Come as you are. Walking down Duval Street (which is basically the Bourbon Street of Key West), you’re just as likely to see a group of older tourists in shorts and sneakers as a throng of gay men in tank tops and gold jewelry. You’ll also see everyone sipping from plastic cups, as open container laws do not apply here.
There’s no doubt that Key West is a drinking town, but it has so much more to offer: beautiful beaches, cultural and historical sites (like Ernest Hemingway’s former home), national parks, and water sports like paddleboarding, snorkeling, and windsurfing. (The temperate water means you can swim year-round.) Old Town Key West is beautiful to wander—it looks like a cross between Charleston and Savannah with its palmetto-lined streets and brightly-colored houses.
When it comes to getting to Key West, it’s choose your own adventure. Many cities offer direct flights to Key West International Airport. You can also drive by following U.S. 1 South as far as it goes, crossing the Seven Mile Bridge, which offers gorgeous views of the blue-teal waters. If you happen to be in southwest Florida, you can take a ferry from Fort Myers Beach or Marco Island—but sail at your own risk. If the water is choppy that day, you could end up sea sick for the 3.5-hour journey (this happened to my husband—sorry, sweetie!).
A weekend is the perfect amount of time to stay in Key West. Whether you’re traveling solo or with a partner or group, here’s where to stay and what to eat, drink, and do.
Where to Stay
Marquesa Hotel.
Marquesa
Tucked a few blocks away from the hustle and bustle of Duval Street, this boutique hotel encompasses three carefully restored Victorian homes (which are listed on the National Register of Historic Places). The rooms are spacious and beautifully appointed, and each building has its own pool and lush interior gardens. The historical yet tropical vibe makes you feel like a local.
Ocean Key Resort Spa
Located on Sunset Pier at the north end of Duval Street, this luxury resort offers gorgeous views of the Gulf of Mexico, Key West Harbor, and—you guessed it—the sunset (it’s where everyone goes to view it). Inside, you’ll find tropical décor and pastel-colored walls. Lounge by the pool overlooking the ocean where the Gulf meets the Atlantic, and order tasty cocktails from their poolside bar, Liquid. And don’t forget to hit the spa, where you can indulge in anything from a relaxing stone massage to a detoxifying mud wrap.
Where to Eat and Drink
Ocean Key Resort Spa.
Hot Tin Roof
You’ll need a reservation for this spot that’s popular with locals and tourists alike. Named after former Key West resident Tennesee Williams’ play, Cat on a Hot Tin Roof, the restaurant offers local seafood and seasonal ingredients infused with Caribbean and Cuban flavors. Be sure to grab a drink at the bar before dinner (I recommend the Hemingway Daiquiri).
Little Pearl
Located off the beaten path, this cozy seafood restaurant is a must. It offers a chef’s tasting menu where every dish is a winner (though I highly recommend the oyster stew). Choose from three seatings at 5pm, 7pm, or 9pm. Reservations are recommended.
The Roost
If you’re looking for a bar that’s smaller and quieter than the ones you’ll find on Duval Street, head to this hidden gem, which offers craft cocktails at an old-school mahogany bar.
General Horseplay
Just off Duval, you’ll find this indoor/outdoor bar where live music is the main draw. They’re also known for their Old Fashioned cocktails—they even offer a class on how to make them.
The Green Parrot
For the quintessential Key West experience, check out this dive bar that’s been around since 1890. A favorite of locals, it offers tons of cold beers on tap, live music seven nights a week, and a pool table and dart board if you’re in the mood for a little friendly competition.
What to Do
The Ernest Hemingway Home Museum.
Ernest Hemingway Home Museum
Key West was home to Ernest Hemingway for more than a decade. You can visit the prolific author’s home and wander the preserved rooms and lush gardens. If you’re a budding writer, you may want to sign up for the home’s Writing Experience, which allows you to work in Hemingway’s former writing studio.
Fort Zachary Taylor Historic State Park
This park has one of Key West’s best beaches. It’s a bit rocky (so you may want to bring your water shoes) but there are equipment rental shops where you can get what you need to go snorkeling, windsurfing, kayaking, and paddleboarding (you may even see a tropical fish or two). There’s also a snack bar, charcoal grills, and shaded picnic areas so you can grab a bite afterwards.
Harry S. Truman Little White House
Take a tour of this historic home, which served as the winter White House of President Truman from 1946 to 1952. The house also hosted a slew of famous guests, like Thomas Edison and six former American presidents.