10 Best Things to Do in Key West

Mallory Square is the central hub for the city’s main restaurants, shops, museums, and theatres. Live entertainment abounds in every street corner, featuring everything from local bands to dynamic street performers. Here you’ll find ice cream shops with just about every flavour your heart desires as well as many vendors offering colourful souvenirs and trinkets to bring back home. 

Mallory Square is also famous for sunset celebrations – 2 hours before sunset, the festivities welcome hundreds of people with magicians, jugglers, clowns, psychics, local musicians, artists and, of course, the glowing Florida sun sinking into a red Gulf of Mexico horizon.

The small town feel of Key West makes it one of the best cities to explore by bicycle. Rent a bike (or bring your own) and ride down the southern coast to Smathers Beach, the largest public beach in the Keys. The beach begins at Mile Marker 0 and has fine white sand and turquoise waters. Spend the day kayaking or parasailing, before ending it with a classic Key West sunset viewing.

Located in the heart of Old Town Key West, the Ernest Hemingway Museum has been welcoming visitors since 1968. As the last home of one of America’s highest regarded authors, the museum is open for 30-minute guided tours every day from 9am to 5pm. 

Aside from showcasing each room as was left by the revered author, the tour also includes a showing of the home’s famous gardens and pool. Cat lovers will be happy to hear that the museum is home to 40-50 six-toed felines, most of which are descendants from Hemingway’s own polydactyl cat, Snow White. 

The Conch Tour Train, established in 1958, has a long history in Key West. Not as long as the revered gastropod used to make tasty fried conch fritters, but close. Hop aboard for the hour-and-a-half tour starting at Front Street Depot and ending at Mallory Square, and learn the history behind the characters and buildings that make Key West famous.

An excellent pro-tip from previous train riders: if you are here for only a day, the Conch Tour Train is a great way to cover a lot of territory quickly. If you’re here for an extended stay, take this tour your first day to get a good lay of the land.

Truman’s Little White House is a historic Key West site where presidents such as Taft, Eisenhower and Truman himself relaxed and decompressed. The house was used as Taft’s winter White House from 1946 to 1952 and was also home to Thomas Edison during World War I. 

These days, 20-minute guided tours are offered every day from 9am to 4:30pm. The tour includes a viewing of the botanical garden that surrounds the property with nearly 1 acre of tropical foliage. 

One of the best ways to take in the beauty of Key West is by boat! Watch the sun rise with an intimate yacht outing or view a splendid Florida sunset during a champagne-filled getaway. Various companies throughout the Keys offer just about everything, from all day party cruises to dinner focused boat trips. 

Wakeboard, parasail, or water ski on emerald waters, or stay dry and enjoy them from aboard a glass-bottom vessel! Whichever way you wish to experience the coast, Key West’s got it. Book in advance for great discounts off many tours.

For those who enjoy a drink or 2 once the sun goes down, Duval Street is the place to be. Dozens of venues dotting this vibrant street become alive at night and lasts into the early morning. Classics such as Hogs Breath Saloon have been around for over 2 decades serving great food and unique cocktails. 

Duval Street is also home to an active LGBT community and a great place to check out nationally recognised drag shows at places such as Aqua Nightclub, 801 Bourbon Bar, and Le Te Da Club.

Found where the Atlantic meets the Gulf of Mexico, this protected park in Key West offers an activity-filled day out with clear water ideal for swimming and snorkelling, as well as nature trails to explore. Snorkelling gear is available for rent in the park, with reams of tropical marine life to see just a short swim offshore. 

Stop by Fort Zachary for a guided tour to learn about its role in the Civil and Spanish-American wars. Take a lunch break at Cayo Hueso Cafe or use the park's public picnic tables and grills to prepare your own meal. Those who linger on into the evening are rewarded with spectacular sunsets. 

The Southernmost Point is a black and red concrete buoy in Key West. This small landmark marks the southernmost point in the continental United States. The buoy is located on the corner of Whitehead St. and South St. and is free to the public. 

If you’re travelling with a group, expect to wait in line for about 10–20 minutes, as only 1 person at a time can go up for a selfie. The buoy is located in an area that features classic Old Florida homes and plenty of beautiful photo-ops.

One of the most popular places to get your picture taken in USA is in front of the ‘Mile 0’ sign, which marks the beginning of the famous interstate US 1. Locally known as the Overseas Highway, US 1 stretches from Florida to Maine, and connects many major cities in the eastern side of the States. The street sign is usually surrounded by visitors wanting to get the perfect shot.