12 Things To See and Do in Key West

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  • Key West, a tropical paradise in the Florida Keys, is the perfect destination for those seeking a Caribbean-like experience.
  • Some of the best beaches in the United States are in Key West, all with beautiful views and warm, calm waters, making it the perfect place to take the family or party it up with friends.
  • Key West has a rich history, making it a cultural touchstone unlike other glitzy island destinations.

Key West is an island and city located in the Florida Keys archipelago. Sitting at the southernmost and easternmost tip of the United States, it’s as far as you can go in those directions without leaving the country.

While Key West has fewer than 30,000 inhabitants, the island receives 100 times as many travelers every year. With its white-sand beaches and opaline waters, it’s no mystery why. A unique blend of culture and Caribbean-like weather await you in Key West. Here are some of the top things to do and see on the island.

1. The Road to Key West

Most people fly directly into the Florida Keys. While this is certainly efficient, traveling to Key West by car provides a unique and wonderful experience.

Getting to Key West by car means taking US 1, also known as the Overseas Highway. This mesmerizing highway is renowned for its incredible views of the ocean, the other islands in the Keys, including Fiesta Key and Key Largo, and the road’s 42 bridges, including the famed Seven Mile Bridge. It’s a long trek by car, but if you love a road trip and have the time, you’ll be glad you took it. You may even want to rent a convertible for the trip.

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2. Watch a Sunset in Mallory Square

If you start your drive early in the day, you’ll have plenty of time to take in a world-famous Key West sunset before settling in for the night. Praised by travel connoisseurs and budget-minded tourists alike, sunsets in Key West are what dreams are made of.

Mallory Square is the best place to take it all in. Packed with dozens of restaurants and street vendors, the square comes to life when the sun starts dipping. Performers and artists flow into the streets, and the alfresco eateries heat up their grills. Pull up a chair at any one of them, order a cocktail, and enjoy a great free show.

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3. Soak in the Sun and Catch Some Waves

Let’s be realistic: If you’re taking a trip to Key West, it’s because you want some serious sun and beach fun. With some of the best beaches in the United States, who can blame you? White sand leading to blazing blue waters and calm currents await. A few you’ll want to check out are:

  • Tiny but famous, South Beach and the South Beach Pier are first stops on any respectable Key West vacation.
  • Rest Beach and Higgs Beach, two amazing beaches linked by a massive wooden pier, are great for regular beach outings.
  • Travelers with tag-along canine companions will want to visit Dog Beach with their pets.
  • If you want something a little less crowded, Smarthers Beach features the largest stretches of sand in Key West.

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4. Visit Ernest Hemingway’s Old Home

The charm and stunning beauty of Key West have drawn many creative and artistic types over the years. Playwright Tennessee Williams lived on Florida’s southernmost island for a while, and it’s said he went to South Beach every day for a swim.

Another famous writer made Key West home before moving to Cuba: Ernest Hemingway. It’s only fitting that his novella, “The Old Man and the Sea” won him a Pulitzer Prize. Today, his old home, preserved as it was when he lived there, is a museum. The Ernest Hemingway Home and Museum offers a glimpse into the personal life of one of history’s greatest writers.

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5. Take In the Historic City Center

Key West’s valuable location as a port has resulted in a very colorful history spanning hundreds of years. A lot of that history still stands in the city center on Duval Street.

Framed by Victorian-era homes on all sides, Durval Street offers a glimpse into the past of an island paradise. These days, the beautiful homes, still painted in tropical pastels, are boutique shops and delicious restaurants.

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6. Experience the Untouchable Nature of Dry Tortugas

One of the most fascinating places in Key West boasts nature that’s almost untouched: Dry Tortugas National Park, located on an island you can only reach by seaplane or ferry.

The beautiful Fort Jefferson today serves as the island’s visitor center. Dry Tortugas is relatively tiny — in just over 30 minutes, you can cover the whole thing. But that leaves plenty of time to enjoy its four beautiful beaches and take in its majestic natural beauty. As an aquatic paradise, it’s one of the best places to go snorkeling or diving.

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7. Spend an Afternoon at the Historic Seaport

Filled with beautiful architecture and countless restaurants, art galleries and boutique shops, Key West’s historic seaport is a remarkable place to spend the afternoon with friends and family.

Swing by the Key West Museum of Art and History to discover the island’s history while touring a magnificent home built in 1891. Wrap things up by heading to the marina to hop aboard a sailboat tour or stroll peacefully on the Harbor Walk while the sun sets.

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8. Attend a Wine Tasting on a Sailboat

Beautiful calm waters and breathtaking sunsets (and sunrises) make Key West a favorite for sailing enthusiasts. You can find numerous sailing options all over the island ready to help you climb aboard a catamaran and sail the seas of the Florida Keys.

Many of these voyages provide access to a delicious buffet of appetizers and, depending on the type of cruise you choose, wine and beer tastings. You can’t go wrong watching a magnificent sunset on a sailboat with fine wine on your lips.

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9. Fall in Love with the Homes

It’s hard to overstate how impressive the classic Victorian homes on Key West are in both ambiance and number. The Old Island Restoration Foundation was formed to preserve Key West’s historic legacy, including these stunning homes.

The former high-season home of President Harry Truman, in particular, draws the curiosity and attention of many tourists. Truman loved Key West so much that he purchased the house and turned it into his “Summer White House.” These days, it’s a lively museum.

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10. Have a Rum-Loving Good Time at Hemingway Rum Company

Affectionately known as “Papa” among his fans and the locals in Key West, Hemingway still has a strong influence on the island. In addition to his home-turned-museum, and more than one watering hole dedicated to the novelist, the Hemingway Rum Company pays homage in its own way.

Visit its warehouse for guided tours to learn about the sugar fermentation process and, of course, sample the product. Papa would have loved it.

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11. Spend a Day in Fort Zachary Taylor State Park

Fort Zachary Taylor State Park is home to an ages-old fort built to defend from maritime invaders, as well as one of the most beautiful beaches on the entire island. Guided tours allow you to practically smell the gunpowder from the cannons while walking the walls and learning about its history.

When you’re done learning and touring, the majestic beach has facilities for renting chairs, tents and snorkeling equipment. You’ll definitely want the latter to explore the crystal-clear waters here.

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12. Try the Famous Key Lime Pie

And of course, how can you visit Key West without indulging in a delectable slice of key lime pie? Originating in the Florida Keys and made from the region’s tinier, sweeter limes, the dessert is the pride of Key West. Head down to The Stone Crab for a homemade, graham-cracker key lime pie topped with freshly whipped cream.

There are few places where you can enjoy the pure joy and fun of an island getaway while also being surrounded by rich culture and history at every exotic bend. Key West is one of those places. Florida’s southernmost city delivers a getaway you’re unlikely to forget, no matter who you travel with.

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Tim Kaechle

Tim Kaechle

Tim Kaechle is a freelance writer and digital nomad who loves learning and creating things for the web. When he’s not busy writing about his myriad of interests, he’s brushing up on his programming and digital design skills, all while wandering the world. He’s currently kicking around in Brazil and planning his next big adventure.

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