Key West, Florida, Is a Perfect Winter Getaway — With Nightlife, Stunning Beaches, and a Historic State Park

Get ready for sun, sand, and plenty of fun.

You don’t have to break out your passport to spend a few days in an island paradise. Just head to Key West, Florida.

Key West is home to some of the most spectacular beaches in America, and dare we say, the world. Its gin-clear waters that lap up against white-sand beaches will leave you in awe. Its vibrant community and fun nightlife will leave you with lasting memories. And its water activities — like snorkeling, diving, and deep-sea fishing — will keep you active from the moment you arrive to the moment you leave.

"Key West has hundreds of years of interesting and infamous history, which includes pirates, shipwrecking, treasure, rum running, military exploits, and billionaire's ventures,” Analise Smith, founder of Key West Food Tours, told Travel + Leisure. “Its melting pot of culture and turquoise ocean surroundings has given way to a vibrant food scene, which includes the most delicious selection of local seafood and tropical fruits.”

Smith added, “When deciding why to come to Key West, it might be a shorter list to ask, 'Why not?' And either way, you'll have a hard time convincing yourself out of the idea.”

Ready to plot out your Key West vacation? Keep reading about where to stay, eat, and play for a Key West getaway you’ll never forget.

Best Hotels and Resorts

Marquesa Hotel

The Marquesa Hotel embodies the Key West spirit through and through. The hotel, which was voted one of the best resorts in Florida by T+L readers in 2023, is classically styled with dark wood flooring and easy breezy island furnishings, and a bright blue exterior paint color that matches the nearby sea. Don’t miss the on-site Café Marquesa for an upscale meal.

Ocean Key Resort & Spa

Ocean Key Resort & Spa has perhaps the most coveted address in all of Key West: Zero Duval Street. The hotel — also voted one of the best resorts in Florida by T+L readers in 2023 — could not be more conveniently located and boasts spacious rooms and suites, each with an epic view of the ocean or Duval Street.

Sunset Key Cottages

For a little bit of luxury and solitude, find your way to Sunset Key Cottages, which was a T+L reader favorite in 2022. The resort sits nestled on a 27-acre private island just off the coast of Key West, and offers up to four-bedroom abodes so even large families can vacation together.

Checa Lodge and Spa

Travelers looking to get out on the water for a sport fishing adventure should make the Checa Lodge and Spa their home base. The resort can help you set up a boat charter for the day to fish just off its shores. Then, head back to the resort for a fantastic seafood dinner at one of its three restaurants: Atlantic’s Edge, Mia Cucina, or Nikai Sushi.

Best Things to Do

“Though we are only a four-mile by two-mile island, we are chock full of ‘must experience’ things to do,” Smith said. Here are a few not-to-miss highlights.

Ernest Hemingway Home and Museum

Celebrate the life and work of Key West’s literary great, Ernest Hemingway, with a visit to his former residence-turned-museum, aptly named The Ernest Hemingway Home and Museum. The home is perfectly preserved just as he left it in the 1930s. It showcases personal items and antiques — and displays the very areas where he penned some of history’s greatest novels. The museum is also home to a large colony of polydactyl (six-toed) cats, which are all descendants of Hemingway's own feline companions.

Southernmost Point

Go ahead and take an iconic Instagram photo at Southernmost Point. The massive buoy, built in 1983, marks the location of, as the name suggests, the southernmost point in the United States. It has become a popular destination for visitors in Key West to also mark their time on vacation with at least a photo of two.

Fort Zachary Taylor Historic State Park

Explore a bit of American history with a visit to Fort Zachary Taylor Historic State Park. It is home to the largest archive of Civil War armament on Earth. It also has a gorgeous beach that is open to the public for swimming, snorkeling, and outdoor dining. As the southernmost state park in the continental United States, it is yet another cool spot to visit when in Key West.

Key West Food Tours

Get a taste of what Key West has to offer with Smith's Key West Food Tours. Smith offers a variety of tours, including a tasting and cultural tour showcasing the island’s Cuban and Caribbean flavors, along with a seafood experience, bar crawl, and even a food tour dedicated to Hemingway.

Best Nightlife

The Green Parrot

As one of the oldest bars in Key West, The Green Parrot is the place to be to mix and mingle with locals. The bar is well-known for its local music and its stellar drinks, but don’t come hungry as it only serves snacks.

The Bull and Whistle

Enjoy even more of the Key West weather by sipping a cocktail or a cold beer at The Bull and Whistle, an open-air bar right on Duval Street. The bar offers table seating facing its small stage for local acts, a large bar to belly up to, and plenty of pool tables so you can challenge your travel companions to a game.

Aquaplex

Key West has a vibrant drag scene, and there’s no better place to experience it than at Aquaplex. The nightclub puts on shows every Monday and Tuesday at 9 p.m. and every Wednesday to Sunday at both 7 p.m. and 9 p.m., giving you plenty of opportunities to see your favorite act.

Best Restaurants

According to Smith, the best part about dining in Key West is that no matter where you go, you’ll likely end up with a great view. “The local grocery stores and even the fast food chain restaurants have ocean views,” Smith said. But perhaps more importantly: “The food is so fresh and local — you'll likely eat delicious sustainable fish and shrimp here that you won't see anywhere else in the country.”

Blue Heaven

Start your day in Key West off with a delicious bang with a visit to Blue Heaven. The restaurant serves breakfast, lunch, and dinner, but is most well-known for its outrageously good morning menu. The popular pancakes are made from scratch and come in plain, banana, pineapple, pecan, or blueberry. Meanwhile, its shrimp and grits come with a side of its famous Betty's Banana Bread.

Garbo’s Grill

Dig into some seafood delights with a meal at Garbo’s Grill. The diner specializes in quick and easy bites like its Cayo Fish, made with red cabbage, mango, jalapeno, cilantro, onion, and its house Caribbean sauce over whatever the fish of the day is. Also notable is its highly beloved lobster roll, crafted with Maine Lobster meat and mayo on a buttered and grilled roll.

Azur Restaurant

For an upscale evening in Key West, head to Azur Restaurant. The Mediterranean eatery sits a few blocks off of Duval Street, providing a quieter atmosphere to enjoy a luxurious meal. The menu includes the likes of Key West pink shrimp in a lemon butter and garlic sauce, and steamed mussels in a rosemary and tomato broth.

Kermit’s Key West Key Lime Shoppe

No visit to Key West would be complete without getting at least a slice, or two, or heck, an entire key lime pie. Find the sweetest of the bunch at Kermit’s, a one-time roadside stand turned popular bakery with two locations in the Keys. The shop sells other dessert treats, but none can top its key lime pies and pie bars. And if you really fall in love with them, you can always have Kermit’s shipped to anywhere in the continental U.S.

Best Time To Visit

The best time to visit Key West is from January to May, when the temperatures around the rest of the nation tend to dip, but remain relatively constant in the Keys.

“Winter tends to be a guest favorite,” Smith said. “There's not too many U.S. destinations that are still running snorkel and dive trips in January, and are booking out their outside dining faster than their inside tables. When it's snow and icicles everywhere else, we are our company motto: ‘Sun, Rum, and Key lime pie.’”

However, Key West is home to several stellar annual festivals throughout the year that are worthy of planning a trip around. That includes The Key Lime Festival, which typically runs in late June or early July, along with Hemingway Days, which honors the life of Hemingway. There’s also Fantasy Fest, a massive, 10-day party extravaganza held in late October, which includes parades, drag performances, costume contests, and a pageant to crown the King and Queen of Fantasy Fest.

How to Get There

There are two ways to get to Key West: drive or fly. There are direct flights to Key West International Airport (EYW) from all around the country, including flights from Chicago, Dallas, New York City, Boston, Charlotte, and Atlanta.

Though it could take you longer, driving to Key West from Miami is an experience all on its own. Visitors can rent a car in Miami and hop on the US 1, known as the Overseas Highway, which takes guests across 113 glorious miles and over 42 bridges, with epic views from start to finish.

How to Get Around

Smith noted that “walking and bicycling are the transportation of choice” in Key West. However, there are a few other modes of transport you can try.

Uber: Uber is operational in Key West. It’s available to and from the Key West International Airport.

Taxi: There are several local taxi services operating in Key West, including Key West Taxi and D.B. Taxi, both of which operate 24/7.

Pedicab: Want more of a scenic ride? Hop on any of the pedicabs traversing Key West. The rides are much more expensive than traditional cabs but do come with a lot more fun. You can also book pedicabs in advance for tours around town. 

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