Unique Things to Do in Key West

by Sian Marsh  |  Published September 19, 2018

Just 106 miles from Cuba, Key West is a small slice of the Caribbean in the United States. Here are 12 unique things to do on, and off, the island from feeding nurse sharks to visiting Hemingway’s home.

Sunset at Mallory Square (Photo: W. Tipton via Flickr)

Key West has developed from a busy trading post, making riches off wrecks in the 19th century, to a content, slow-paced city known for its endless summers and Caribbean flare. This, along with the copious museums, bars, outdoor activities and diverse cuisines, makes the string of islands an ideal year-round destination.

See the sunset at Mallory Square

Lying on the northwestern side of Key West, Mallory Square is the place to see one of the two biggest natural events of each day: the sunset. Crowds gather early at waterside spots, listening to reggae booming from buskers’ amplifiers and setting the scene for this Caribbean sunset while sipping on BYO drinks. As the sky starts to darken, hues of orange and red disperse in horizontal lines; even when it’s cloudy the colours manage to seep through. The spectacle starts an hour before sunset, with the depth of colour strengthening as the event nears. Eventually, on non-cloudy days, the sphere of orange light will finally disappear beneath the horizon and the crowds disappear almost as quickly as the darkness falls.

Mallory Square, Key West

Trinkets for sale in Mallory Square (Photo: Frank via Flickr)

Feed sharks at the Stoned Crab

Nurse sharks gather in the small harbour at Ibis Bay Beach Resort which sits alongside the alfresco Stoned Crab restaurant. Twice nightly, customers from the restaurant have the chance to feed the sharks from the dock, creating a spectacle of thrashing tails and splashing water. Then feed yourself at the Keys-style restaurant, which serves classic seafood dishes – steamers (a pot filled with steamed shell-fish of your choosing), fish fillets with rice, seafood towers and pastas. All the fish and shellfish are sourced locally from Florida Keys fishermen. To accompany the traditional fresh fish dishes is a large selection of Margaritas, served at the Eco Bar, as well as classic cocktails such as piña coladas, frozen daiquiris and mojitos, plus signature mixtures and local beers.

3101 N Roosevelt Boulevard, Key West

Take a seaplane to the Dry Tortugas

Dry Tortugas National Park lies 68 miles to the west of Key West. Hundreds of visitors head to the main island, Garden Key, every day to walk the walls of Fort Jefferson, swim off the golden sand beach and snorkel in the clear, coral-laced waters. For a more intimate and faster mode of transport to the island board a seaplane and fly over the Gulf of Mexico to the destination. Over the duration of the 45-minute flight, rays, sharks, turtles and shipwrecks can be seen in the sapphire and emerald waters, as well as the Marquesas, another small group of islands roughly halfway between Key West and the Dry Tortugas. Inflight commentary from the pilot provides information about the history of the fort, shipwrecks and these two sets of islands as well as pointing out the wildlife.

Dry Tortugas National Park, Key West

Explore Bight Marina

Half Shell raw bar, Bight Marina (Photo: Bachmont via Flickr)

Rows upon rows of boats moored to wooden docks surround the edge of Key West. Bight Marina in Downtown Key West is one such area and is a refreshing place to explore. Starting at the north end of Duval Street, the wooden promenade suspended over the water winds around the outer edge of multi-story buildings. Restaurants, bars, shops and art galleries line the walkway while floating docks spill into the water where boats moor. Meander along the jetties to survey the boats, watch as the large tarpon gather in the shallows when fishermen unload their daily catches, peer in the galleries to see the work of local artists or stop in one of the lively bars for a refreshing drink or snack. The Half Shell Raw Bar is a favourite with a fresh oyster bar and locally caught fresh fish cooked in various ways.

Bight Marina, Key West

Visit the Ernest Hemingway Home and Museum

Hemingway Home and Museum (Photo: John McCullough via Flickr)

Set up much as it was when Hemingway himself lived in Key West, the Hemingway house sits on a large plot along Whitehead Street, boarded by a red brick wall. The square, whitewashed, Spanish-Colonial style house is set back amid lush green palms which hide the building’s façade from the road making it feel more secluded on entry. Inside is airy and spacious, with minimal décor. Dark wood and tiled floors help to keep the house cool. Bookcases full of old leather-bound books line the walls in the hallways and numerous other rooms. Portraits of Hemingway are proudly shown with snippets of information about his early life through to his death. Perhaps the most unusual and interesting feature of the house are the six-toed cats that sleep on Hemingway’s bed and roam the garden looking for a shady spot under the palms.

907 Whitehead Street, Key West

Climb the stairs of the Key West Lighthouse

A white-painted brick lighthouse rises from the grounds of the Keeper’s Quarters Museum on Whitehead Street. The 22-metre-tall tapering tower was decommissioned in 1969 and opened as a museum displaying artefacts from Key West’s maritime heritage, including belongings and photographs of previous lighthouse keepers. This is, in fact, the second lighthouse to occupy this spot, the original was destroyed in a hurricane in 1846 with this replacement opening in 1848. Visitors can climb the 88 steps to the top of the lighthouse to peruse the museum displays and venture out on the black, wrought-iron balcony for uninterrupted views over the western shore of the island and out to the Gulf of Mexico, where ships can be spotted on the horizon.

938 Whitehead Street, Key West

Tour Fort Zachary Taylor

Fort Zachary Taylor lies on the west side of the island amid vast areas of greenery and arid sandy land in what is now an historic state park. The U-shaped, red brick fort was built in 1845 following the war of 1812; one of many built to aid defence of the southeast coast of the United States. Tour the historic structure at your own pace or join the guided tour which commences most days at 11am. Barracks were housed in the straight building enclosing the grassy centre of the U-shaped fort. They remain sectioned off in small compartments, some of which are set up as they were in the Civil War. The fort itself is open on the inner side and remains very basic with large cannons lined up in their firing positions. On the upper level of the fort more cannons can be seen; some are even buried in the concrete base. From here there are endless views out over the water.

601 Howard England Way, Key West

Walk along Smathers Beach

Entrance to Smathers Beach (Photo: Trvlto via Flickr)

Weaving along the southern edge of Key West is a narrow strip of golden sand. The main highway runs along the same route, however they are separated by a think border of palms and other tropical grasses and shrubs. Weathered wooden boardwalks lead from the pavement through the scrub to the thin beach and the endless water. Towards the western end of this strip the scrub makes way for a wooden promenade that twists between stand-alone palms and Australian pines. It is ideal for cycling or walking. Here the sand strip also becomes slightly wider allowing room for volleyball courts where locals gather and play.

Smathers Beach, Key West

Have a drink at Sloppy Joes

The neon sign of Sloppy Joe’s (Photo: Valerie via Flickr)

The bright red light of the Sloppy Joe’s sign contrasts with the dark, dingy interior. Large doorways remain open throughout the afternoon and evening, enticing passers-by into the loud, atmospheric bar which is often packed with revellers. Ernest Hemingway frequented Sloppy Joe’s when it was located around the corner from here, where Captain Tony’s Saloon is now. Live bands perform on the large stage throughout the day. Styles of music range from country to rock and pop; sometimes they are mixed with comedy acts. The bar serves classic American food in baskets including burgers and nachos. Iced, slushy drinks are somewhat of a thing but draft and bottled beer is also served.

201 Duval Street, Key West

Try some outdoor activities in Fort Zachary Taylor Historic State Park

Surrounding Fort Zachary Taylor is the Fort Zachary Taylor Historic State Park. Dense areas of Australian pine hide nature trails built for walkers and bicycle paths which often lead out to the pristine beach. Here, many water sports are on offer, from kayaking and canoeing to snorkelling, scuba diving and paddle boarding. Alternatively, spend the day relaxing on the beach, lying on the sandy shore, and occasionally cooling off in the clear, warm water. Camping is allowed in the park with toilet and shower facilities available as well as designated picnic areas. The beach here is another perfect spot on Key West to see the tropical sunset; one that is a lot more serene than Mallory Square.

601 Howard England Way, Key West

Discover the streets away from the tourist area

Traditional Key West House (Photo: Erica via Flickr)

The area between Duval Street and Mallory Square make up the main tourist spot on Key West. This region is always busy with people strolling the streets, wandering in and out of shops, restaurants and bars. Music can always be heard. However, there is a much quainter side to Key West. All around this main area stand idyllic residential homes; clapboard houses painted in pastel colours with picket fences along the street edge and verandas containing rocking chairs placed among potted plants. Small boutiques and quieter restaurants inhabit these streets, offering local produce and cuisine. El Siboney is a local favourite serving Cuban cuisine. Firefly is good for a modern take on traditional southern food.

Take a boat trip

Situated in the middle of the Gulf of Mexico with numerous harbours along the coast, Key West is a boating city. Hundreds of boat trips leave every day, heading out into the shallow backcountry and the deep sea. Party boats leave noisily in the afternoon, complete with all-inclusive fruity cocktails and snacks, while dive trips and fishing charters often have an early start. Dive the colourful coral reefs or try macro diving in the mangroves. Combine diving with fishing by using spear guns to catch game fish or stay on the boat, using a line and hook to catch marlin, mahi-mahi and swordfish. Smaller fish such as bonito and jacks can be caught on the reefs. Alternatively, ferries take passengers to small, uninhabited islands just off Key West for exploration of dry land, by way of the water. On any boat trip it is possible to see loggerhead turtles, small sharks and large rays soaking up sunrays on the water’s surface.

Bight Marina, Conch Harbor Marina, or Galleon Marina, Key West