Key West

Key West, historically known as Cayo Hueso (Bone Island), is an iconic island city situated at the southernmost end of the Florida Keys. The settlement was formally chartered in the 1820s, rapidly growing into one of the wealthiest cities per capita in the country through maritime salvage, shipwreck wrecking, sponging, cigar manufacturing, and salt production. This historic affluence is reflected today in the preservation of the largest historic district on the National Register of Historic Places in Florida, boasting hundreds of late-nineteenth-century wooden cottages adorned with elaborate fretwork, wraparound verandahs, and lush tropical flora.

The island is equally defined by its unique geographic location, where the shallow Gulf of Mexico meets the deeper Atlantic Ocean. This setting creates a dynamic subtropical ecosystem comprising extensive sea grass meadows, protective mangrove forests, and the continental United States' only living coral barrier reef. Beyond its natural appeal, Key West maintains an eccentric, tolerant, and artistic cultural identity that was famously embraced by figures such as Ernest Hemingway, President Harry S. Truman, and playwright Tennessee Williams. Modern visitors encounter an inviting blend of history, relaxed tropical hospitality, and vibrant aquatic leisure.

Reasons to Visit

• Explore the Ernest Hemingway Home and Museum, populated by dozens of famous polydactyl (six-toed) cats.
• Snorkel or scuba dive the vibrant coral reefs of the Florida Keys National Marine Sanctuary.
• Gather at Mallory Square for the famous nightly sunset celebration featuring street performers, artists, and live music.
• Tour the Harry S. Truman Little White House, Florida's only presidential museum.
• Swim, snorkel, and discover nineteenth-century military brickwork at Fort Zachary Taylor Historic State Park.
• Embark on a day trip to the remote Dry Tortugas National Park and historic Fort Jefferson.

Things to Avoid

• Avoid driving your vehicle into Old Town; parking is strictly regulated, expensive, and heavily enforced with towing.
• Do not touch, stand on, or anchor directly onto living coral reefs during snorkeling and boating trips.
• Avoid booking sunset cruises or watersports tours last minute during peak winter and spring break periods without advance reservations.
• Do not harass, feed, or touch the wild feral chickens that roam freely across island streets, as they are protected by municipal ordinances.

Local Transportation Tips

Key West is remarkably pedestrian- and cyclist-friendly thanks to its flat terrain and compact geographic footprint. Bicycle rentals are the most practical and popular way to explore, with numerous rental vendors offering daily and weekly rates. For motorized local transit, the Duval Loop provides a free, air-conditioned bus service connecting the historic Seaport, Old Town, and Duval Street every 15 to 30 minutes. Metered taxis, ride-hailing services (Uber and Lyft), and street-legal electric golf carts are also readily available for journeys across New Town and to Key West International Airport (EYW).

Travel Etiquette

• Embrace the island's unhurried 'island time' demeanor; service and dining pacing are deliberately relaxed.
• Casual resort attire is accepted nearly everywhere, but cover-ups and shirts are expected when leaving the beach for shops and restaurants.
• Always tip marina deckhands, snorkel instructors, and boat captains 15% to 20% for water-based charters.
• Respect historic private residences and residential quiet zones in Old Town, particularly late at night away from Duval Street.

Recommended Age Group

Key West welcomes travelers of all generations, though its atmosphere and activities cater most strongly to older youth and adults.

• Babies (0-2 years): Neutral. Tropical humidity, intense midday heat, and uneven historic brick sidewalks can pose logistical challenges for stroller use.
• Kids (3-12 years): Recommended. Young travelers enjoy the Key West Butterfly & Nature Conservatory, the Key West Aquarium, shipwreck museums, and calm catamaran snorkeling excursions.
• Teens (13-19 years): Recommended. Older children appreciate active watersports like parasailing, paddleboarding, snorkeling coral reefs, and exploring ghost tours by night.
• Adults (20-64 years): Recommended. An outstanding destination for dining, craft cocktails, historical exploration, sailing, and a vibrant nightlife scene.
• Seniors (65+ years): Recommended. The flat terrain, accessible hop-on trolley tours, rich literary heritage, and warm climate make the island very welcoming to mature travelers.

Accessibility Level: Medium

• The Old Town Trolley and Conch Tour Train offer wheelchair-accessible transport options covering major island landmarks.
• Fort Zachary Taylor Historic State Park provides specialized beach wheelchairs with oversized balloon tires for shore access.
• Key West's flat island topography makes it accessible for manual and motorized mobility devices, though some historic brick walkways present minor root heaves.
• Major museums, including the Hemingway Home (ground floor and grounds) and Truman Little White House, feature ADA accessibility routes.

Did You Know?

In 1982, Key West humorously seceded from the United States to protest a Border Patrol roadblock established on the Overseas Highway. Declaring itself the independent 'Conch Republic,' the mayor symbolically broke a loaf of stale Cuban bread over a U.S. Navy officer's head before immediately surrendering and applying for one billion dollars in foreign aid. Today, the Conch Republic identity remains a beloved symbol of island independence and humor.

Cool Statistics

• Official distance from Havana, Cuba: roughly 90 miles (closer to Havana than to Miami).
• Number of polydactyl (six-toed) cats residing at the Hemingway Home: approximately 60.
• Square mileage of the island: approximately 4.2 square miles.
• Average annual days of sunshine: over 260 days.