Nestled at the extreme south of American territory, Key West stands out for the quality of its beaches, historic monuments, and coral reefs, making it a premier tourism destination. Plan your next Florida getaway with the help of this practical Key West guide.

Key West, A Hidden Gem of the Keys Archipelago

If there is one road in the United States that mesmerizes with its vistas, it is surely the one traversing the Keys and the island of Key West. This route is known as the Overseas Highway. Key West is a charming town at the southern tip of Florida, cradled between the Atlantic Ocean and the Gulf of Mexico. Key West is a blend of sunshine, rocky beaches, and palm trees. The finest beaches and diving sites are concentrated at Bahia Honda State Park. It is not solely the coastal charm that draws tourists to Key West; cultural and urban tourism actually rival seaside appeal. Uncover secrets hidden behind military fortifications, visit the luxurious estates of Ernest Hemingway or John Audubon, stroll through historic mansions, elegant cafés, and shopping centers along Roosevelt Boulevard. Historic museums line Duval Street. Hit the road to Key West and experience a dream road trip through the Florida Peninsula!

History

The island's history, originally named "Cayo Hueso," began in 1763, when the English seized Florida by force, driving the Calusa Indians to neighboring Cuba. After a long period of conflict among the English, Spanish, and Native Americans, the island officially joined the Union in March 1822.

Its strategic position on the Florida Strait drew the attention of businessmen. John Sompton conceived of launching an urban development program. He divided the island into four separate parcels. Leveraging his connections in Washington, he successfully sold the island to American settlers: John Whitehead, John Fleeming, John Mountain, and John Warner, along with Pardon C. Greene, who became known as "the founding fathers of Key West."

While the city was born from a bidding transaction, it rapidly modernized thanks to an ambitious development plan featuring major civil works and road projects. Its importance grew during the Civil War as it hosted a strategic naval base. Grand fortification projects were undertaken: Fort Zachary Taylor, Fort Jefferson, and the East and West Martello Towers, which served as artillery and munitions depots.

Following the Civil War, Fort Jefferson was repurposed as a prison. Its most famous inmate was Dr. Samuel A. Mudd, convicted for treating President Abraham Lincoln's assassin. It took the arrival of the Overseas Highway in 1938 to transform the city's fortunes, as it became connected to mainland Florida. An initial access road had been constructed in 1912, but the Labor Day Hurricane destroyed it entirely in 1935, claiming the lives of over 400 American veterans working on its construction.

Today

The city is home to nearly 26,000 residents according to the latest 2020 census. Its golden age has passed. It seems distant now, the era when Key West was the most prosperous city on the Florida Peninsula. Nevertheless, this resort town remains a sought-after destination, serving as a port of call for cruise ships and welcoming tourists from around the world.

What to See and Do

Beyond its coastline, Key West abounds with monuments, museums, and interesting places to explore. Use our list to organize your visits.

Architectural and Historic Heritage

Ernest Hemingway's House

Do not miss the magnificent historic residence that Ernest Hemingway called home. This towering figure of American literature lived there for a dozen years, between 1927 and 1939, with his second wife and children. The architecture showcases Spanish colonial style. Push through the entrance to encounter Hemingway's polydactyl cats, which boast more digits than typical.

Fort Zachary Taylor

Construction of the fort began in 1845, a few years after Florida joined the Union. Though somewhat remote, the fort is worth visiting for its striking red-brick arcades that reflect Irish and British architectural heritage, for its beach with crystal-clear waters—among Key West's finest—and for its spectacular sunset views (especially from the western shore). Swimming is not particularly recommended due to rock formations, but it is an excellent spot for scuba diving.

Truman Little White House

Inaugurated in 1890, the Truman Little White House stands as one of Key West's most significant historic monuments. Until 1846, it served as a base camp for American naval forces before becoming a winter retreat for President Harry S. Truman. Today, the former White House has been converted into a museum, complete with recreational facilities and offices for senior government officials.

Natural Heritage

Bahia Honda State Park

This reserve features the island's most beautiful beaches. Those who love relaxation can laze on pristine sand, while the more active can venture to Siloé Island and its coral reefs. With abundant marine life to behold—corals, colorful fish, and wild dolphins—the Florida Keys National Marine Sanctuary is a renowned diving destination. Driving from Key West, you can reach Bahia Honda State Park in about 45 minutes.

Urban Heritage

Duval Street

Duval Avenue, named in honor of Florida's first governor, is heavily frequented by tourists. As you stroll along, keep your eyes open for Victorian mansions, art galleries, and cafés. Afro-Bahamian and Spanish influences blend within these historic walls. Do not miss the Southernmost House, a historic inn from the late nineteenth century that has hosted five American presidents among its guests.

Mallory Square

If you find yourself near 400 Wall Street, linger at Mallory Square, a vibrant waterfront district known for its restaurants and shops.

Key West Butterfly Conservatory and Botanical Gardens

Visiting this wildlife park is a delight for those who adore butterflies. Over 60 different species from around the globe are housed here. The site is located at the end of Duval Street.

Practical Information

When to Visit

The best time to vacation in Key West is between April and September, when sunshine prevails and rainfall is minimal. If your vacation goal is to spend time in the water, summer is ideal. Otherwise, plan your departure for May or mid-September to take advantage of discounts on flights and hotel rates.

You can reach Key West by air, road, or sea. The city's airport is served by major carriers such as Delta Airlines, American Airlines, and Cape Air. Charter flights are also arranged by tour operators.

Nearby Attractions

Before arriving in Key West, several tourist sites along the Overseas Highway are worth exploring:

• Everglades National Park;
• Marathon resort town and its renowned bridge;
• Key Deer Wildlife Refuge, which protects endangered deer species.