How to Spend 48 Hours in Key West

Downtown Key West with souvenir shops

 TripSavvy / Taylor McIntyre

Key West has a long history of being a destination for renegades and those wanting to get away. While mostly known for Duval Street today, there is much more to explore, including a fascinating history of getting rich off of shipwrecks to an amazing island ecosystem. Here’s how to balance your trip between debaucherous fun and memorable experiences that will show you why everyone from Jimmy Buffet to Ernest Hemingway have a soft spot for Key West.

01 of 06

Day 1: Morning

The Pool at the Gates Key West

Courtesy of The Gates Key West

10:00 a.m.: Your first stop: your hotel, The Gates Key West. The Gates is a beachy haven that offers up live music happy hours every day. It’s also a part of a larger hotel complex so you can enjoy the amenities of all three hotels, not just one. As soon as you drop your bags go grab some breakfast from their very tasty food truck, The Blind Pig. Claim a lounge chair on the large lawn and have your first encounter with the chickens of Key West—they’re everywhere!

11:00 a.m.: If you’re already craving some time on the water, grab a seat at the Gates’ pool bar. You’ll often find locals here, who are filled with countless stories of Key West back in the day. Once you’ve had some time to unwind, catch the shuttle that takes hotel guests downtown where you can see all the famous sites and where the party really gets going. 

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02 of 06

Day 1: Afternoon

Inside the Key West Aquarium

TripSavvy / Taylor McIntyre 

1:00 p.m.: The hotel’s shuttle will drop you off near Mallory Square, in the heart of downtown. From here, browse local souvenir shops and grab lunch at long-time local favorite Blue Heaven, where chickens peck around your feet while you dine. Their pancakes are famous but you also can’t go wrong with their savory dishes like lobster and grits . No trip to Key West is complete without sampling the famous dessert that originated here: Key Lime Pie. Grab your slice at Café Sole.
2:00 p.m.: The main square is packed with museum options. Watch rescued sea turtles train with their new prosthetic fins or feed stingrays at the Key West Aquarium, or climb the tower for a great view of Key West. Head to the Shipwreck Museum to learn about Key West’s maritime bounties, or see literal treasure at the Maritime Museum.

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03 of 06

Day 1: Evening

Sunset in Key West

TripSavvy / Taylor McIntyre

5:00 p.m.: After learning all about Key West’s past and present, treat yourself to a signature rum cocktail at Papa’s Pillar Distillery. Located in an old tobacco warehouse, the distillery doubles as a shrine to Hemingway. If rum isn’t your drink of choice, head to Duval where you have plenty of options to quench your thirst. Try the Smallest Bar in Key West, a bar with two seats but a great view to watch the spectacle of Duval Street, or check out Sloppy Joe’s, a Key West establishment that opened the day prohibition was repealed. If you’re feeling really adventurous, try Garden of Eden, a clothing-optional rooftop bar.
7:30 p.m.: Key West is famous for its spectacular sunsets. On a clear day, you can even see a green “spark” the moment the sun sets below the horizon. There is no better spot to see this phenomenon than Mallory Square. Each night,Mallory Square has a sunset celebration where street performers do everything from juggle, swallow swords, or play music.
9:00 p.m.: For dinner, head to El Meson de Pepe, which serves menu of Cuban classics with a lively backdrop of music and dancing. The bar features live salsa music and patrons and passersby alike often dance around the restaurant. If you’re still feeling energetic, head to Irish Kevin’s, which offers an eclectic mix of locals and tourists and live music every night. Virgilio’s is another great spot—a slightly classier option where you can dance and enjoy the best martinis in Key West. 

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04 of 06

Day 2: Morning

Southern Most Point Buoy

TripSavvy / Taylor McIntyre 

10:00 a.m.: After a night on Duval, you’ll want an easy morning, so sleep in and recover a bit. If you’re up and ready for the day, catch the shuttle to downtown for a refreshing mimosa at Moon Dog Café, a local café and bakery with cheery interior that will put you in the island mood.

11:00 a.m.: After refueling it’s time to head to Key West’s best gimmick–the Southernmost Point. Technically the true southernmost point of the continental U.S. is on Ballast Key, a privately-owned island, while the southernmost point of Key West is actually on the island’s naval base. But alas,why let facts get in the way of a great photo op? Travelers stand in a long line to grab a photo with the large red and black buoy boasting you’ve made it as far south as possible. If you’re not up for the line you can settle for a photo of the buoy itself. Local attractions litter your path on the way down to the “southernmost” point: pass by the Mile Marker 0 sign, another popular photo stop, or. visit Hemingway’s former house and see the colony six-toed cats. Just down the street from the buoy, you’ll find Key West Butterfly and Nature Conservatory, where you can walk through swarms of colorful butterflies. 

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05 of 06

Day 2: Afternoon

Tour boat with kayaks trailing behind at sunset

TripSavvy / Taylor McIntyre

2:00 PM: Head back to the north end and enjoy a bountiful lunch of freshly caught seafood. Conch Republic Seafood Company offers Caribbean style dishes along with more traditional steaks and ribs. If you don’t mind getting off the main strip for a bit, grab a seat at the much calmer Half Shell Raw Bar. Here you can enjoy a table on the water and a mountain of food, for half the price of its Duval Street competitors. Try your best not to eat yourself into a food coma as you have an activity-filled afternoon ahead! 


4:00 PM: The best part of Key West is getting out on the water and exploring the ecosystem that surrounds the Keys. Fury Water Adventures Key West offers a number of tours from dolphin spotting trips to sunset cruises. The Island Adventure and Sunset Cruise Combo is the perfect option if you want to experience a bit of everything. The afternoon cruise departs at 4 p.m. and will take you snorkeling off the coast, kayaking through mangroves, discovering wildlife on the sandbars, all while cooling off with unlimited drinks. Both the morning and afternoon cruises provide meals;however, only the afternoon cruise lets you watch the sunset from the middle of the ocean—a true delight!

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06 of 06

Day 2: Evening

Jim Powell playing the saxophone at the green parrot bar

 Courtesy of The Green Parrot

9:00 p.m.: Once you’ve docked, keep the party going at 801 Bourbon Bar. This bar has themed nights that feature everything from drag shows to karaoke. Green Parrot is another local favorite that is a self-described haven for shady “hi-jinks and misadventures,” but in truth it’s a “good-vibes-only” dive bar with a rotating roster of live music every night. Once your feet start dancing, head to Rick’s Key West, a DJ-driven space that stands out among the live bands along Duval Street. It’s a multi-level dance club that has eight different bars in the complex so you should never have to wait that long for a drink. 

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