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The Conch Connection

The Most Unforgettable Things to Do in Key West in the Summer

Updated on: Feb 14, 2024 3:07:05 PM

There are so many fun, exciting, and historical things to do in Key West, that even despite challenging times, tourism has stable growth!

In 2018, Key West hosted an astounding 5.1 million visitors. That's 1.5 percent more than the previous year!

3.8 million of those visitors were domestic travelers looking for some leisure and downtime. 300,000 were domestic business travelers. And over 1 million were international visitors.

In total, these tourists spent almost $2.4 billion on lodging, shopping, food, entertainment, transportation, and more. These numbers prove that there's no lack of fun to be had in this tropical, sun-filled, waterside destination.

To ensure you have the best time ever—whether you're a local, an international traveler, a businessperson, whoever!—check out our list of the best stops and must-dos this city has to offer!

Visit the Ernest Hemingway Home & Museum

Ernest Hemingway had quite the connection to Key West, even becoming a part of its epic story. He wrote his novels here, lived here, loved here, fished here, traveled to Cuba from here. . . He and the Florida Keys were a match made in heaven!

Ernest Hemingway Home in Key West showing paintings

Photo Credit: Piqsels

The home and museum details some of that history, all the way to a penny that is  immortalized in the ground near the pool—Hemingway lived there for over ten years with his many cats (generations of descendants of whom still reside there—and many that have more than five toes per paw!). The home has several rooms, a lush backyard and garden, a pool, and a wonderful bookstore.

Make sure to add this spot to your itinerary! 

Take Your Picture Next to the Southernmost Point of the Continental US

The US' Southernmost point, located at the corner of South Street and Whitehead Street, represents the place where Cuba is a mere 90 miles away. 

There's a large concrete buoy that makes for a perfect photo opportunity, and you can usually expect a small line of people waiting for their turn.

The notable spot is located near streets with tons of things to do, from dining and shopping to bar hopping or beach dwelling, so you can easily swing by.

Walk Down Famous Duval Street

Duval Street is excellent for both partiers and spectators alike, as there's everything from bars and kiosks to retail shops, renowned nightclubs, and plenty of places to eat.

Their shops feature a mix of everything—Key West souvenirs, made-on-site t-shirts, music, outdoor gear, shoes, and world-class art galleries, to name a few—and span the entirety of the blocks. You'll find popular dining options like Margaritaville and the Hard Rock Café, plus small, family-owned establishments. 

Depending on when you visit, Duval Street is also home to several annual events, such as the 10-day adult-centered Fantasy Fest, the Key West Food & Wine Festival, and the week-long Conch Republic Independence Festival. 

Spend Some Time (And Probably Some Money) at Mallory Square

Mallory Square is known as a hub for Key West's social and commercial life. It's a daily networking of entertainment, shopping, museums, and more, that's been there since the city's inception in the 1820s. 

Mallory Square Key West at Sunset

Photo Credit: Piqsels

If you love taking photos of Key West's beautiful landscape, you'll love the view of the Square's sunsets. As the sun slowly drops below the horizon, you'll notice the tips of passing sailboats gliding by. Enjoy people-watching, cats that jump through hoops of fire, and all you can eat or drink.

There's something for everyone here!

Have a Bite or a Drink at Sloppy Joe's Bar

Of all the things to do in Key West, this restaurant is worth a visit or even a walk-through.

Sloppy Joe's is a famous (and infamous) saloon that's been in operation since 1933. It's also still known as the US' Southernmost outpost (not to be confused with the buoy we mentioned earlier).

The name itself was boasted to be Sloppy Joe's (after going through two other names first) by none other than Hemingway himself. He loved to hang out here, enjoying the interesting crowd that always seemed to magnetize to it. 

The famous bar and restaurant is located on the corner of Greene and Duval Street, and serves up Key West snacks like shrimp, conch fritters, fish dip, and Havana nachos. Midway through your day, take an hour or so to relax here, listen to live music, and drink a Sloppy 'Rita or a Rum Runner with locally-made rum.

Check Out Harry Truman's Little White House

Hemingway isn't the only prolific name to be attached to Key West's identity.

Former President Harry Truman also lived here, in a now-famous Presidential Museum (Florida's only one!).

Our 33rd President spent 175 days of his presidency in this Little White House, from 1946 to '52, which was initially constructed in 1890 as housing for naval officers. From here, he dealt with such historical moments as the Civil Rights movement, the rebuilding of Europe, and responding to the Cold War.

And Of Course, Swim at the Beaches

You can't go to Key West and not enjoy the water. You can swim, rent boats, snorkel, scuba dive, fish—whatever your water-loving heart desires. 

Key West Beach

Photo Credit: Piqsels

There are beaches all over Key West, natural and human-made, so you can pick and choose! Some of the best beaches include:

  • Smathers Beach (which boasts a two-mile-long shoreline)
  • The Dog Beach, for those who bring along their four-legged family member on vacation
  • Higgs Beach, which is a little more serene than Smathers, and has a shoreline full of palm trees

Feel free to ask your fellow bartenders, servers, and local shop owners which beach is their favorite. They can guide you to a great beach—although finding one on your own won't be a problem!

Of All the Things to Do in Key West, How Can You Choose?

We'll let you in on a little secret—you don't have to choose!

You can enjoy all these activities and more in one single trip. Everything is within decent proximity, allowing you to explore all you want to of Key West. The city is only four miles long, and two miles wide—do it all!

The Key West Express can get you where you need to go, and it's one more of the fun things to do in Key West. So, contact us today with any questions about our lounge-worthy ferry!

Hero Image Photo Credit: Pixabay

Topics: Water Activities, Activities, Waterfront, Walking Distance, Beaches, Casual, Old-Town, Shopping, Beach, Snorkeling

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