The best things to do in Key West

It’s quite possibly the No. 1 reason tourists come to Key West: to hit the largely divey bars along and near Duval Street. You can pay a guide for a pub crawl, but for your own self-guided tour, start at a Hemingway favorite, Sloppy Joe's, before continuing on to the old classics, Hog's Breath, Captain Tony’s and Green Parrot. On the second day, hair-of-the-dog your way to Schooner Wharf, 801 Bourbon, La Te Da, Sunset Pier and whatever other bar you stumble past, because, as Hemingway said: “Drinking is a way of ending the day.”

Those rented scooters you’ll see darting everywhere will get you there faster, but there’s no better way to take in the island than on a rented beach cruiser, available pretty much everywhere around town (there’s a reliable one just north of U.S. 1 and Duval). Start with a stop at 5 Brothers Grocery for a Cuban coffee and sandwich eaten on the benches out front. Head south to Higgs Beach to walk the bikes out on the pier. Ride past the Hemingway House and the Truman White House before a scenic cruise onto the sand at Fort Zachary Taylor Beach. End the day by rolling up to Mallory Square to watch the entertainers before sunset, riding back to your rental, most likely with something cold in one hand.

Open daily, step into the chaotic life of Ernest Hemingway at this historic home and museum. A tour of the house and grounds takes about 30 minutes and includes a peek into the gardens, rooms and pool that Hemingway called home. You'll also notice some interesting cats prowling the location – these are said to be the descendants of the famed, original six-toed cat that Hemingway lovingly took care of while residing here. To go truly immersive, book the $1,500 Hemingway Home Evening Writing Experience and get three hours of access to the grounds, when you can finally start that great American novel of yours.

Seventy miles west of Key West is Dry Tortugas National Park—a great spot for exploring, learning and soaking in the crystal clear waters of Key West. The national park is known for its top-notch bird watching with over 300 species of bird known to circle the area. Snorkeling is also a favorite activity and waters rarely get deeper than 15 feet. When it’s time to dry off, take a walk around Fort Jefferson and have a scenic lunch at one of the picnic tables.

Duval Street is easily the most popular street in Key West, and for good reason. The bustling thoroughfare is known for its plethora of bars, restaurants and nightlife establishments. While most locals tend to stay away from the tourist- and cruise-ship-passenger–flooded part of town, no trip to Key West is complete without visiting and walking down the iconic street.

Located at 24 degrees 33 minutes north latitude and 81 degrees 45 minutes, The Southernmost Point is exactly what it seems—the southernmost point of the United States (though there is some debate). Easily one of the most photographed places in Key West, the line for a selfie can get long, but it moves quickly, especially as high tide rolls in and water starts to flood the street near the landmark. For the best photos possible, check what time low tide will be or go early in the morning when the air is clear.

The biggest draw in Key West is the ocean, of course. Book a boat tour to get out on the water. Tours can take place during the day or at night and offer activities like snorkeling, sandbar hopping and private dinners on board. Tours with Key West Boat Trips start at $450 for six people, but splitting that between friends makes this excursion a cheap and fun day trip.

The former chicken farmer Mel Fisher helped create a modern-day treasure-hunting industry when he discovered the wreck of the Nuestra Señora de Atocha in Florida waters. Now the company that bears his name, with a small museum near Mallory Square, offers treasure-hunting dive trips. Pricing and details are worked out per trip, but perhaps uncovering that lost horde will pay for your vacation. 

It wouldn’t be a trip to Key West without some time in the sand, and Smather’s is the largest public beach on the island. The beach begins at mile marker zero and stretches on for about half a mile, so you don't have to worry about it getting too crowded. Along the shore, there are cute shops and restaurants to pop into while you wait for sunset—believe us, it will be glorious.

Florida’s only presidential museum is the Harry S. Truman Little White House in Key West. Built in 1890 as housing for naval officers, the home was most famously used by former President Truman as a vacation stop—he spent 175 days of his presidency there—though other notable figures who have stayed here include Thomas Jefferson and John Kennedy. The home is open daily for tours, which run every 20 minutes until 4 p.m.

The Overseas Highway connects Key West and other parts of the Florida Keys to mainland Florida. Stretching 113 miles across the Atlantic, the expanse takes about four hours to travel across (one way), but the scenery makes it worth it if you're considering driving to Keys. Along the way, you'll hit Key Largo, Islamorada, Marathon, and more before stopping in Key West. For a mini road-trip, drive the Seven Mile Bridge between Marathon and Key West—it's nothing but blue skies and bluer water the whole way.

Got a history buff in your party? Fort Zachary Taylor is home to the largest collection of Civil War cannons in the United States, and the fort itself dates back to 1845. Alongside its historic collection, Fort Zachary Taylor also offers excellent fishing and snorkeling at the nearby beach and a network of trails with good bird- and people-watching.

The Key West Lighthouse has been a focal point of the island since 1848 when its first keeper was a woman (nearly unheard of in the 19th century). Since its construction, it underwent numerous upgrades—including being made taller and the introduction of electricity—until it was decommissioned in 1969. Today, visitors can climb the 88 steps to the top for breathtaking views of Key West. Don't forget to peek into the keeper's quarters, too, for a glimpse of maritime life in the late 1800s.

If this is your first time in Key West, consider soaking up local sights and knowledge aboard the Conch Tour Train. The trolly tours take you past some of the most iconic sights in Key West like The Hemingway Home, the Southernmost Point and the Harry S. Truman Little White House. The best part? You can hop on and off as many times as you like – so feel free to spend hours marveling at the six-toed cats at the Hemingway Home before getting back on the train.

Located in historic Mallory Square, in the middle of Key West's tourist district, the aquarium hosts an array of ocean creatures to observe, including jellyfish, sharks, reef fish, conch, and sea cucumbers. Kids can get up close and personal with sea stars, sea urchins, and horseshoe crabs at the touch tanks, and the entire family will love learning about the resident sea turtles on the Sea Turtle Conservation Tour to see what the aquarium is doing to protect the species in the wild.