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. Two 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.

Rent a bike (or bring your own) and ride down the southern coast to Smathers Beach, the largest public beach in the Keys. The small town feel of Key West makes it one of the best cities to explore by bicycle.

The Smathers 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. The laid-back atmosphere combined with the scenic coastline is an ideal combination for a day of relaxation.

Located in the heart of Old Town Key West, the Ernest Hemingway Home & Museum has been welcoming visitors since 1968. As the last home of one of America’s highest regarded authors, the museum is open daily and offers 20 to 30 minute guided tours.

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 nearly 60 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 1-hour 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.

Harry S. Truman 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.

Today, visitors can enjoy 30-minute guided tours offered daily. Additionally, you can explore the nearly 1-acre (0.4-hectare) botanical gardens surrounding the property through a self-guided, free tour. These gardens feature a rich array of tropical foliage, providing a serene backdrop to this significant historical landmark.

One of the best ways to take in the beauty of the island is to take a Key West boat tour. 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 the party 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.

Fort Zachary Taylor Historic State Park, located where the Atlantic meets the Gulf of Mexico, is a protected gem in Key West offering a day packed with activities. The park features clear waters perfect for swimming and snorkelling, with snorkelling gear available for hire to explore the vibrant marine life just offshore. Nature trails provide opportunities for exploration and adventure.

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 Buoy is a black and red concrete buoy in Key West. This small landmark marks the southernmost point in the continental USA. 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 iconic photo spots in the USA is in front of the 'US 1 Mile Marker 0' sign, marking the beginning of the famous interstate US 1. Locally known as the Overseas Highway, US 1 stretches from Florida to Maine, connecting numerous major cities along the eastern side of the USA, offering breathtaking coastal views.

The Mile Marker 0 sign is often surrounded by visitors eager to capture the perfect shot to commemorate their journey through the historic route.