It’s Always 5 O’Clock on This South Florida Island
There’s no shortage of reasons to party on Key West, but there are quirky museums and snorkeling spots too.
Often referred to as Miami’s backyard, Key West is the southernmost island in the Florida Keys. It’s the kind of destination that others hop on planes to visit. But, with minimal planning, you can get there by lunch when hopping in the car from Miami.
Perhaps best known as a haven for dive bar-lovers, the people in Key West always seem to be living their best Jimmy Buffet life. There's always something to celebrate, from festivals dedicated to the namesake dessert and Ernest Hemingway to parties every night as the sun goes down.
But beyond the booze there’s plenty of other fun things to do. Both on land and in the water, the area is rife with historic sites dating back to the early 1800s, and, of course, opportunities to gorge yourself on conch fritters abound. From ghost tours to pirate lore to a presidential museum, you’ll be plenty busy until it's time to watch the sunset at Mallory Square and begin an evening filled with live music and bar hopping.
Drive time:
3 hours and 30 minutes from Miami, Florida
If you don’t do anything else: Celebrate the sunset in Mallory Square
In a city that loves to party as much as Key West, it just makes sense that there’s a reason to celebrate every single day. Rain or shine, winter or summer, the sun goes down—and so, the denizens of Key West party at Mallory Square’s world famous Sunset Celebration. It’s located on Wall Street—conveniently named because there’s just a low wall that separates the pedestrian-only street from the ocean—just west of the northern end of Duval street. Every night during the two hours before the sun sets the street becomes flooded with performers, vendors, and live music, a tradition that’s been taking place since the ’60s. Visitors are invited to watch magicians, artists, psychics, and more as they entertain and share their talents while the sun slowly creates a pink-orange hue in the sky.
Fill Your Days:
Outdoor activities in Key West
Located 70 miles west of Key West’s coast, the 100-square miles that make up Dry Tortugas National Park are only accessible by boat or seaplane, making it a remote must-see. The park is made up of seven islands and lots of open water. Take a roughly two-hour ferry from downtown Key West to Fort Jefferson, which happens to be the largest brick masonry structure in the Americas (made of over 16 million bricks), where you have the option of exploring on your own or taking a guided tour of the six-sided unfinished fortress. With less than 1% of the park being land, the crystal clear waters are ideal for swimming, snorkeling, and diving. There’s more than 30 types of coral and hundreds of species of marine animals including tropical reef fish, lobster, grouper, sea turtles, octopus, and more. There’s also tons of local jet ski tours, party boats, and snorkel tours available via Fury Key West.
Museums in Key West
From Ernest Hemingway’s House to Harry S. Truman’s Little White House (aka Florida’s only presidential museum), there’s so much history to discover on the 4.2 square mile island.
At the Key West Shipwreck Museum you’ll find actors, films, and actual artifacts that tell stories of 400 years of shipwreck salvage in the Florida Keys. A visit to the Mel Fisher Maritime Museum may stir up some desire to do a little treasure hunting of your own, as the museum is home to countless treasures (think: a 77-karat emerald, gold chains, gold and silver coins, massive bricks of silver, and parts of the actual ship) from the Spanish galleon Nuestra Señora de Atocha that sunk during a 1966 hurricane. The bounty made Fisher one of the world’s most successful and well known shipwreck salvagers after he found it off the coast of Key West in 1985 after a 16-year search. Looking to do a little searching yourself? Experienced divers can go down with Fisher’s team to check out the Atocha for themselves while those who are a bit more novice may enjoy snorkeling along the artificial reefs that have been created out of the dozens of sunken ships.
It’s also one of the most haunted cities in America, with no shortage of ghost stories and spooky haunts. From Robert the Doll (who straight-up inspired the Chucky movie series) to The Lady in Blue who is known to make regular appearances at Captain Tony’s Saloon (aka the site where she was hung for murdering her husband and children)—there are both walking and trolley tours for those who love connecting with the dearly departed.
Festivals in Key West
This laidback party town loves a theme and that’s very evident in its festival schedule. In fact, there’s a fun festival on the calendar more than once a month in the Conch Republic. From the Hemingway Days featuring the Annual Hemingway Look-Alike Contest (going on 43 years this July) to October’s wild Fantasy Fest and Truman’s Tropical Fruit Festival in June, there’s a party honoring just about every historical figure, beloved food, and outdoor activity. Seriously though, what other destination do you know of that has a Mermaid Festival and a Key Lime Pie Festival just days apart?
Eat, Drink, and Sleep:
Bars and restaurants in Key West
Prepare your liver—it’s always 5 o’clock down here. There’s no question that famed Conchs (that’s what Key West locals are called) Jimmy Buffett and Alan Jackson were definitely talking about their hometown in that country hit song. This island knows how to turn up and when it comes to day drinking, there’s zero judgment in the Conch Republic. Well-known bars like Sloppy Joe’s, Green Parrot, Rick’s, and The Bull open as early as 9 am (and don’t close until 4 am), happily catering to those looking to get the day started with a killer Bloody Mary, beer, or hell, even a shot of tequila or two. For a slightly fancier cocktail experience, check out General Horseplay where you’ll find creative twists on classic cocktails or Tiki House, which serves up fruity tiki cocktails in cool glassware. All easily accessible down Duval Street, there’s a no frills come-as-you-are vibe inside every watering hole in town. No wonder it was a favorite hideaway for Ernest Hemingway, who was notoriously fond of an ice-cold spirited beverage.
You’re going to need some food to soak up all that drinking. No matter where you grab a table (or bar stool) in Key West, just about every menu is going to have the same three items made in their own unique way: Key lime pie, conch fritters, and Key West pink shrimp. Staples on the island, they’re can’t-miss dishes you’re sure to devour multiple times during your stay. Find great Key Lime pies at Kermit’s Key West, Blue Heaven, and Moondog Cafe. Chow down on conch fritters and Key West pink shrimp at Southernmost Beach Cafe, DJ’s Clam Shack, or Thirsty Mermaid. If you’re looking for something a bit different, opt for Cuban food at El Siboney, fish sandwiches at B.O.’s Fish Wagon, heavily stuffed tacos at Garbo’s Grill, or great sushi Misohappy Sushi & Thai.
Hotels in Key West
From boutique hotels to vacation rentals and a plethora of Airbnbs, there are tons of places to stay on this little island. The Southernmost Beach Resort offers a range of room categories including newly renovated 18th century Victorian guesthouses, a private beach, and three pools; while Havana Cabana is a Cuban-inspired tropical oasis with mojitos upon arrival and the island’s largest pool. Orchid Key Inn is adults-only while The Island House and Alexander’s Guesthouse cater to gay men and are known for being quite a riot. And no matter where you decide to stay, you’re never far from the action.