Top 15 Attractions and Activities in Key West, Florida

At the far end of the Overseas Highway, and at the southernmost point of the continental United States lies an island and city distinct from any other in the country.

The contemporary history of Key West commences in the early 19th century when the Florida Keys served as a graveyard for heavily loaded and misdirected vessels.

Their wrecks became the foundation of an entire industry, with ‘wreckers’ salvaging treasures and materials from these lost ships.

Currently, Key West epitomizes watersports, leisure, and some of the most breathtaking sunsets I have ever experienced. Meanwhile, Duval Street stands as one of the premier destinations for nightlife in America.

Key West serves as an excellent starting point for diving excursions, acting as the gateway to the idyllic Dry Tortugas National Park, while a significant artificial reef lies just offshore.

1. Mallory Square

The social life of Key West has centered around this waterfront plaza for over 200 years. It is an unparalleled attraction where locals gather to share news and engage in shopping.

Mallory Square hosts the Sunset Celebration, occurring 365 days a year. Few alternatives offer a better perspective for witnessing the sun’s descent.

Visitors begin to arrive two hours before sunset. As the sun sets over the Gulf of Mexico, you can shop for arts and crafts, enjoy a meal, and observe skilled street performers.

A brief tour of Key West history can be explored at the Memorial Sculpture Garden, which features busts commemorating key local figures and a monument dedicated to the Wreckers who settled the island in the early 19th century.

2. The Ernest Hemingway Home and Museum

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The Ernest Hemingway Home and Museum, located on Whitehead Street, is the most frequented paid attraction in the city. Hemingway resided here with his wife Pauline Pfeiffer from 1931 to 1939.

Built in the French Colonial style, the house dates back to 1851, and it was here that he produced a number of acclaimed short stories and nonfiction works, including “Green Hills of Africa” (1935) and “The Snows of Kilimanjaro” (1936).

The residence still contains many of Hemingway’s belongings, notably the writing room, which can be viewed through a screen.

Additionally, polydactyl cats roam the grounds, purportedly descendants of the author’s famous six-toed cat, Snow White.

3. Fort Zachary Taylor State Historic Park

At the southern tip of Key West, a Civil War-era fort stands as a defense for the continental United States. This installation began in 1845, well before the war, and remained operational during both the Civil War and the Spanish-American War (1898).

The fort’s corridors are well worth exploring, housing what may be the largest collection of Civil War cannons in the nation.

Further south lies a small pebbly beach, with the allure stemming from its calm, clear waters ideal for snorkeling. Water shoes are recommended for the best experience on this beach.

4. Duval Street

The primary thoroughfare of Key West, Duval Street, spans 1.25 miles and serves as the nucleus of the city’s nightlife. Notably, this street connects the Gulf of Mexico in the north to the Atlantic Ocean in the south.

Its vibrant reputation arises from an extraordinary concentration of bars, with more nightspots per capita than in any other location within the United States.

Currently, there are 43 bars, and if, by an extraordinary feat, you manage to visit all of them, you will have accomplished the Duval Crawl. However, it is not advisable to undertake this challenge in one evening.

5. The Harry S. Truman Little White House

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In the late 19th century, Key West served as the site of a naval station that played a pivotal role in the Spanish-American War. Following World War II, the building became the winter retreat for President Harry Truman.

Ultimately, he spent 175 days of his presidency at this winter residence. Notably, subsequent presidents also utilized the facility, including Eisenhower, who recuperated here after a heart attack.

Moreover, in 1961, JFK held a summit with Harold MacMillan here, returning in 1962 following the Cuban Missile Crisis.

The property has been designated a State Historic Site and museum since 1991, offering tours filled with interesting anecdotes. I found it particularly moving to see “The Buck Stops Here” sign placed at Truman’s desk.

6. Key West Butterfly and Nature Conservatory

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For those visiting Key West with children, the Key West Butterfly & Nature Conservatory is an excellent addition to your itinerary. Ideal for a rainy day, this climate-controlled facility houses over 60 butterfly species from around the globe.

Within this glass-domed space, vibrant butterflies flutter freely among lush rainforest plants and blossoms. Additionally, more than 20 bird species, turtles, and a pair of striking flamingos share the environment.

A 15-minute introductory video educates visitors regarding the lifecycle of butterflies and covers intriguing facts about different species. In the Learning Center, you can further explore their anatomy and origins.

7. Southernmost Point of the Continental USA

When contemplating Key West, one iconic image that often comes to mind is the concrete buoy marking the seawall. Situated at the intersection of Whitehead and South streets, this monument, established in 1983, is a classic photo opportunity.

A glance at maps reveals a more southerly point at Fort Zachary, which is accessible to the public; however, the actual southernmost point lies on United States Navy property, making it off-limits to visitors.

As with all locations on this side of Key West, my preference is to visit during sunset.

8. Mel Fisher Maritime Museum

Mel Fisher, a resident of Key West, was a renowned treasure hunter who uncovered multiple shipwrecks in Florida’s waters. His most significant discovery occurred in 1985 with the Spanish galleon, Nuestra Señora de Atocha.

Located in a historic storehouse built in 1910, the museum is dedicated to Fisher’s endeavors and the area’s maritime heritage. I found the exhibit chronicling his 16-year quest for the Atocha particularly captivating.

Visitors can peruse a myriad of well-presented artifacts retrieved from sunken vessels, including cannons, religious items, jewelry, gold bars, coins, pottery, rifles, pistols, and much more.

Furthermore, a poignant exhibit highlights the Henrietta Marie, a slave ship that sank in 1700 and was excavated in the 1980s.

9. U.S. Coast Guard Cutter Ingham Museum

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This WWII-era Coast Guard cutter, prominent in numerous sunset photographs taken at Truman Waterfront Park, has been preserved as a museum ship.

The USCGC Ingham served from 1936 to 1985 and was actively involved during World War II. Notably, in 1942, while on an escort mission, the ship sank the German submarine U-626.

A self-guided tour allows you to navigate the ship, from the galley to the officer’s quarters. Along the way, preserved items, including uniforms, radio equipment, period furniture, weapons, and even a barber’s chair are on display.

Visitors should be prepared for some steep climbs and descents throughout the tour.

10. Key West Garden Club

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This picturesque oasis by the water boasts ocean views and vibrant tropical gardens, intertwined with a Civil War-era fort.

Distinguished from many local attractions, the Garden Club is free to visit. Alongside its serene atmosphere and photographic opportunities, it is rich in history, dating back to 1863.

The butterfly garden, waterfall garden, fragrant perfume garden, and diverse orchid zones were particularly enjoyable. Periodically, the gentle ocean breeze from the Atlantic enhances the experience.

The fort’s remnants, featuring vaulted ceilings and gun mounts, add an element of romance and intrigue to this unique location.

11. Dry Tortugas National Park

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Key West serves as the launch point to the magnificent Tortugas Islands, located nearly 70 miles to the west, recognized for being the most remote and pristine of the Florida Keys.

These islands are safeguarded by a 65,000-acre national park, of which only 1% consists of land. To fully experience this snorkeling and diving paradise, having your own boat is most beneficial.

However, this option may not be feasible for everyone. Alternatives include seaplane charters and the high-speed Yankee Freedom Ferry.

Dominating the land area is the expansive Fort Jefferson, constructed in 1861. Spanning 16 acres, this fort is the largest brick masonry structure in the Americas and served as a prison for several individuals implicated in the Lincoln assassination starting in 1865.

12. Sloppy Joe’s

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As Key West’s most iconic bar, Sloppy Joe’s has been a cherished establishment within The Conch Republic since 1937.

In its early days, it was a popular gathering place for the famously hard-living Ernest Hemingway and his associates.

Today, Sloppy Joe’s remains a lively venue, featuring continuous live music, quirky special events, and a comprehensive food menu. The conch fritters and the renowned key lime pie are menu highlights.

If you find yourself in Key West during July, be sure to attend the Hemingway Lookalike Contest, a beloved tradition that has persisted for over 40 years.

13. Florida Keys Eco-Discovery Center

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This remarkable visitor center focuses on the extraordinary biodiversity found within the Florida Keys National Marine Sanctuary, encompassing the only coral barrier reef in the continental United States.

Some of my favorite features at the Florida Keys Eco-Discovery Center include a live feed from a coral reef, a replica of the Aquarius underwater laboratory, and a comprehensive interactive map of the Florida Keys.

Additionally, you can view details about over 2,000 ships that have been wrecked in the keys, accompanied by images of their recovered artifacts.

Furthermore, the interactive mangrove exhibit captivates visitors by allowing them to test their skills in identifying the sounds produced by various colorful inhabitants of this habitat.

14. Audubon House and Tropical Gardens

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This historical house was constructed in the early 19th century for Key West’s first harbor pilot, Captain John Huling Geiger.

Significantly, this location is renowned as the residence of the celebrated painter and ornithologist John James Audubon (1785-1851), who stayed here in the 1830s.

Attracted by the surrounding tropical flora, he produced several works in the house and gardens. Audubon also collected cuttings from the gardens for use in many of his artistic creations.

Following hurricane damage, the house was reconstructed in the Classical Revival style during the 1840s. After being slated for demolition, it became the first of many restoration efforts in Key West.

Interestingly, the structure was built using Dade County pine, now an extinct wood, valued for its resistance to decay and imperviousness to termites.

The property features a gallery where visitors may purchase prints of Audubon’s artwork.

15. The Vandenberg

The Vandenberg, an outdated Navy vessel, was sunk off the coast of Key West in 2009 to serve as part of an artificial reef. This site has since become a habitat for a remarkable variety of marine species, including sailfish and Goliath grouper.

Originally launched in 1943, the USNS General Hoyt S. Vandenberg functioned as a troop transport and missile-tracking ship.

This 522-foot-long vessel now rests approximately 150 feet below the surface in the Florida Keys National Marine Sanctuary, situated about eight miles offshore.

Numerous tour and dive options are available from Key West. Please note that advanced certification in deep diving is necessary to explore the site, as unqualified individuals may only visit in the company of a private guide.