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.

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. 

Located between the Gulf of Mexico and Atlantic Sea, Key West has an abundance of fresh Florida lobster, stone crab, and its famous pink shrimp. Seafood restaurants are plentiful throughout the Keys with places such as Conch Republic Seafood Company, DJ’s Clam Shack, and Half Shell Raw Bar taking claim as the favourites among locals and visitors alike. 

For something a little more low-key, head to BO’s Fish Shack and try their grilled hogfish – a favourite all-around!

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.

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.  

It wouldn’t be Key West without a cigar shop on every corner. Some of the country’s most acclaimed cigar factories call Key West home, with Rodriguez Cigar Factory and Key West Cigar Factory having manufactured their famous cigars here for over 80 years. Many of these factories offer daily tours, where visitors can watch the process of cigar-making and even roll one of their own. 

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.

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.