Key West is the last island of the Florida Keys, connected to the mainland via the Overseas Highway, a small town of wooden houses, bars, and harbor piers about 160 km off Florida's southern tip.
Key West is the last island of the Florida Keys, connected to the mainland via the Overseas Highway, a small town of wooden houses, bars, and harbor piers about 160 km off Florida's southern tip. You go for the drive across 42 bridges through the sea, for Hemingway's home, and for the evenings at Mallory Square, when half of Key West applauds the sunset.The journey itself is a highlight of the trip: The Overseas Highway stretches 113 miles from Florida City to Key West. Along the way, worthwhile stops include John Pennekamp Coral Reef State Park in Key Largo, the USA's first underwater park, the beaches of Bahia Honda State Park, and the Old Seven Mile Bridge, whose restored section you can walk or cycle to Pigeon Key.In Key West itself, the Old Town is so compact that you can reach everything on foot or by bike: Duval Street from the Gulf to the Atlantic, the Southernmost Point Buoy, Fort Zachary Taylor with its beach, and in the evenings, the bars where Hemingway himself once drank. If you wish to venture further, take a boat or seaplane from here to Dry Tortugas National Park.
Key West is approximately 6.5 km long and 2.4 km wide. The Old Town, located in the island's west, is best explored on foot or by rented bicycle. Instead of fixed bus lines, the city utilizes app-booked shared buses from Key West Rides On Demand, which also connect to the Lower Keys Shuttle. The special appeal is the mix of Caribbean-influenced wooden architecture, fishing port, and pub culture that has shaped Key West since Hemingway's time. Worth exploring are the area around Mallory Square and Key West Bight harbor to the north, Duval Street as the main axis, and the quieter neighborhood around Whitehead Street with Hemingway House and the lighthouse. For the other Keys, you'll need a car, as beaches, reefs, and bridges are spread along the entire highway.
Sights in Key West and the Florida Keys
Discover the most important sights and attractions
Historic Landmark
1Southernmost Point Buoy
The colorful concrete buoy at the corner of South and Whitehead Street has marked the southernmost point of the continental USA since 1983, with “90 Miles to Cuba” written on it. Because the seawall is being renovated since 2025, a temporary copy stands at the Atlantic end of Duval Street. For your photo, you'll wait less time, especially early in the morning.
Hemingway lived in this house in the 1930s and wrote several of his most famous works here. Dozens of cats live on the property, many with six toes, descendants of Hemingway's cat Snow White. It is open daily from 9 AM to 5 PM, and tours are also available in other languages.
The waterfront square is the evening gathering place for the Sunset Celebration, held nightly since the late 1960s. Roughly two hours before sunset, jugglers, musicians, and craftspeople set up, and as the sun sinks into the Gulf, the crowd applauds.
The army began construction of the fort in 1845; during the Civil War, it remained in Union hands and served as a base against blockade runners. Today, it is a National Historic Landmark with a large collection of Civil War cannons, and just behind it lies a beach for snorkeling and swimming.
The Officer's House of the Naval Base, built in 1890, served as President Truman's winter quarters from 1946, where he spent a total of 175 days. Guided tours available; open daily from 9:30 AM to 5 PM.
The main street, a good 2 km long, runs from the Gulf of Mexico to the Atlantic, lined with wooden houses, bars, galleries, and the Cuban cultural center San Carlos Institute. By day for strolling, by night for a pub crawl.
Cuban family restaurant on Catherine Street with generous portions at fair prices. It’s best to order the Paella Valenciana an hour in advance by phone.
Considered Key West's oldest restaurant, with a weathered wooden house and a small patio on Caroline Street. Great for breakfast, a potent margarita, and a slice of Key Lime Pie.
Since 1992, you've been sitting here in the courtyard under a tree at painted picnic tables, two blocks from Duval Street. Popular for breakfast, the Michelin Guide features it. Breakfast and lunch without reservations, dinner reservations are limited.
The cuisine of the Keys thrives on the sea and on Cuba, which is only about 150 km away. Fish, shrimp, and crabs come fresh off the boat, along with sandwiches from Cuban tradition, and almost always a slice of Key Lime Pie to finish.
Key Lime Pie
Cream made from small, tart Key Limes on a Graham cracker crust, served with whipped cream or meringue depending on the house. By law, it is the official pie of the state of Florida, and in Key West you'll find it on almost every menu.
Conch Fritters
Fried dough balls with chopped conch. The conch gave locals their nickname, Conchs, but it can no longer be harvested in Florida since 1985; today, the meat comes from the Caribbean.
Key West Pink Shrimp
Key West’s pink shrimp, discovered in the Gulf in 1949, sparked a shrimp boom. Enjoy them boiled, grilled, or as a shrimp cocktail.
Stone Crab
Only the claws of stone crabs are harvested; the animals return to the sea. Season: October 15 - May 1.
Cuban Sandwich
Pressed sandwich on Cuban bread with roasted pork, ham, Swiss cheese, pickles, and mustard, likely originating in the cafés of cigar workers. The Key West variant often comes with added mayonnaise, lettuce, and tomato.
History and Culture
The name Key West is an English corruption of the Spanish Cayo Hueso, Bone Island, because Spanish seafarers found human bones here. In the 19th century, the city thrived on fishing, salvaging shipwrecked vessels on the offshore reef, and cigar production by Cuban immigrants. In 1912, Henry Flagler's Over-Sea Railroad reached the island; a hurricane destroyed the railway in 1935, and in 1938 the Overseas Highway took over its role. In late 1949, fishermen off Key West discovered vast stocks of pink shrimp, and the subsequent boom went down in the city's history as the Pink Gold Rush.Ernest Hemingway lived in Key West from 1931 to 1939 and here, among other works, wrote "To Have and Have Not" and "The Snows of Kilimanjaro." President Harry S. Truman spent a total of 175 days between 1946 and 1952 in his winter retreat, today's Little White House.Key West showed its stubborn side on April 23, 1982: In protest against road blocks by border police on the highway, the city council declared the island the independent Conch Republic, declared war on the USA, immediately capitulated, and requested foreign aid. The action garnered so much attention that the roadblocks soon disappeared. The name Conch, as the locals call themselves, has since stood for the island's unique stubbornness.
Standing since 1937 at the corner of Duval and Greene Street, this bar is part of the city's Hemingway legend. Live music plays daily from 10 AM to 2 AM, and the Hemingway Look-Alike Contest is held in July.
The 1851 building initially served as an icehouse and mortuary. Today, a tree, once a gallows, grows through the bar and out the roof. Dark, loud, and full of stories, Hemingway was among its regulars.
Bar with a wooden counter in a late 19th-century building on Whitehead Street, featuring live music almost every evening, often starting from late afternoon. At the counter, you'll quickly get talking with locals.
AirportKey West International Airport (EYW) is served by airlines including American, Delta, United, JetBlue, Allegiant, and Breeze. Many travelers fly into Miami (MIA) or Fort Lauderdale (FLL) and continue by rental car. The airport in Marathon has no scheduled service.FerryThe Key West Express fast ferry connects Fort Myers Beach on the Gulf Coast with Key West. The crossing takes approximately 3.5 hours, arriving at the ferry terminal in Key West Bight on Grinnell Street.CarThe Overseas Highway (US 1) spans 113 miles and 42 bridges from Mile Marker 127 near Florida City to Mile Marker 0 in Key West. Addresses on the Keys are often given using mile markers. Plan extra time during peak season and on weekends, as there's virtually only one road. It's best to leave your car parked in the Old Town.Getting AroundOld Town is best explored on foot or by rental bike. Within the city, Key West Rides On Demand operates, an app-booked shared shuttle bus with connections to the Lower Keys Shuttle. Current schedules are available on the City of Key West website.
Accommodations in Key West and the Florida Keys
Find perfect stay in Key West and the Florida Keys
