How to Spend a 24-Hour Staycation in Key West, Florida (2024)

Just a few hours from Miami by car, Key West offers an easy escape for those seeking relaxation and fun — even if only for a day. The 4.2-square-mile island embraces the philosophy of “it’s 5 o’clock somewhere” all day, every day, and is renowned for its deep affection for Ernest Hemingway and Jimmy Buffett, both of whom famously called the island home.

With everything within walking distance, visitors can easily wander down Duval Street and its neighboring thoroughfares to discover numerous bars, restaurants, museums, and historic sites. Whether seeking enlightenment or leisure, this southernmost island promises a variety of experiences. Here’s a guide to spending 24 hours in Key West.

12 p.m. Arrive just in time for lunch

An appetite has likely been worked up after such a long drive, and now it’s time for lunch. Head to Eaton Street Seafood Market for a casual seafood-filled lunch. Situated in a refurbished gas station, this spot is part market/part restaurant where there’s all sorts of local fresh catch, like hogfish, Key West pink shrimp, lobster, stone crab, conch, grouper, and more. Available for purchase to take home or in an array of sandwiches, salads, tacos, and fried or grilled appetizers that can be eaten on-site.

Another idea: Garbo’s Grill is a food truck that was featured on Diners, Drive-ins, and Dives; B.O.’s Fish Wagon serves some of the best fried fish sandwiches on the island; Misohappy Sushi & Thai has great lunch specials and is right off Duval Street

2 p.m. Explore the Historic Old Town

For such a small island, Key West packs it in when it comes to things to explore. From the house where Hemingway once lived that’s now a museum where several 13-toed cats roam free to Truman’s Little White House (Florida’s only presidential museum) to Mel Fisher Maritime Museum, where visitors can see some of the coolest found sunken treasure, there’s no shortage of museums to check out. For those who want more of a guided experience, there’s always the famed Conch Train that takes guests all over the island and allows them to hop on and off as they please. Or, if a more personal vibe is what’s on the agenda, Island Tales tours by local resident Amy Andrade are fun and informal and take place on her decked-out golf cart. Don’t forget to snap a photo at the famous Southernmost Point Buoy.

Another idea: Get out on the water. Go kayaking with Lazy Dog; go on a snorkeling tour with Sunset Watersports; go parasailing and/or rent a jet ski from Fury Adventures

5 p.m. Head to happy hour at Sloppy Joe’s

A well-deserved drink is in order. After all that exploring, it’s finally time to hit the bars — though no judgment if waiting until 5 p.m. is too hard. Duval Street has great spots to hang out and listen to live music with a co*cktail in hand. One of the most popular haunts is Sloppy Joe’s. With local and visiting bands on stage daily, ice-cold drinks are served quickly, and delicious conch fritters are served with Key lime mustard. It’s a solid choice for a drink any time of day or night. Plus, it’s really close to Mallory Square where the daily Sunset Celebration happens.

Another idea: Green Parrot, Sunset Pier, Tiki House, Hog’s Breath Saloon, and Celtic Conch are all great spots for drinks and bites

6:30 p.m. Go to Mallory Square to enjoy the daily Sunset Celebration

Key West loves a sunset, so much so that they gather to celebrate the sun setting every day of the year. Since the 1960s, locals and visitors have gotten together at Mallory Square — along Wall Street (named that because there’s a low wall that separates the ocean from the pedestrian-only street) — two hours before the sun sets to watch it go down. During this time, visitors will find street food vendors, artists, psychics, photographers, street performers, and more, making it a lively atmosphere that’s a must when visiting Key West.

Another way to enjoy the sunset: Hop on one of Fury Adventures sunset sailings — these party boats offer food, drinks, and live music while cruising around the island as the sun sets.

7:30 p.m. Dinner at Thirsty Mermaid

Locally caught seafood, an impressive raw bar selection, and tasty bites like mac n’ cheese croquettes with truffle aioli are on the Thirsty Mermaid’s menu. Opt for the Mermaid Royale Platter featuring oysters, clams, shrimp co*cktail, and ceviche before moving on to hearty plates like gnocchi with spicy short rib ragu or togarashi spiced yellowfin tuna served with jasmine rice, vegetables, and a coconut green chili sauce.

Other ideas: Family-owned El Siboney for Cuban food; Little Pearl for an evolving four-course chef-tasting menu; or Southernmost Beach Cafe for oceanfront eats

9:30 p.m. Activity Interlude: Take a ghost tour

As one of the most haunted cities in America, Key West has tons of spooky stories to share. There’s an array of walking tours and those that can be taken from the safety of a trolley where the curious can learn all about Robert The Doll (who inspired the Chucky movies) and other tales of the undead who are said to roam about the island. Fun fact: the local cemetery has over 100,000 graves, while Key West only has about 30,000 residents, making the ratio of living to dead kind of crazy to think about.

11 p.m. Nightcap at General Horseplay

Those looking for a proper co*cktail should make their way to General Horseplay, known for its stiff co*cktails and overall tomfoolery. Inside, imbibers will find a large bar and an impressive collection of co*cktails, including those of the smoked variety and clever twists on classics — like a banana bread old fashioned. Head out back for live music and cold beers in a lively backyard setting.

Other ideas: There’s really no wrong answer here. Wandering down Duval Street and popping in and out of the dozens of bars, enjoying a few drinks and live music is always a good time. Most are open until 2 a.m., with quite a few open until 4 a.m., or head to 801 Bourbon for one of the drag cabaret shows that happen nightly at 9 and 11 p.m.

How to Spend a 24-Hour Staycation in Key West, Florida (3)

11 a.m. Brunch at Blue Heaven

Brunch is a must, especially after all that drinking down Duval. Blue Heaven is a timeless institution where chickens roam free, and breakfast takes place in a cute courtyard behind the main building. Serving hearty plates of eggs, grits, pancakes, and a killer breakfast sandwich, this is just what’s needed to round out a quick jaunt to Key West. Don’t skip the Key lime pie, as it’s one of the most talked about on the island and features a baked Alaska-like mountain of torched meringue on top of the creamy, tart pie.

Other ideas: Bagatelle for breakfast tacos, Banana Cafe for banana fosters waffles, Harpoon Harry’s for a seafood omelet, or pop into Matt’s Stock Island just one island over on the way home for a croque Cubana or guava-stuffed French toast

Where to stay: Southernmost Beach Resort, Pier House Resort & Spa, Ocean Key Resort & Spa, The Marquesa Hotel, and Winslow’s Bungalow are all quaint, historic, and beachy spots that perfectly encapsulate the vibe of Key West and are just steps away from all the action.