Much of Key West’s rich history is captured in the buildings lining Duval Street from Mallory Square to the Southernmost Point Buoy. By day, join a walking tour or zip through town on a tourist train, hop-on-hop-off bus, or tiki bike to admire former residences of luminaries like Ernest Hemingway, Robert Frost, and Harry S. Truman. Most tours visit the Old Customs House, Audubon House & Tropical Gardens, Mel Fisher Maritime Museum, and Key West cemetery and lighthouse.
At dusk, set sail from the Historic District on board a catamaran, schooner, or tiki boat for a happy hour cruise, or sample the buzzy nightlife with a pub or cocktail crawl on land. The Old Town is soaked in legends and lore, so delve into the dark side of its history with a ghost tour through the historic center and graveyard.
The Key West Historic District is a must for history and architecture buffs; the elegant mansions make for great photo ops.
Don’t forget sunscreen, sunglasses, and a hat if exploring this tropical island’s Old Town by day.
Pub and cocktail crawls are only open for travelers aged 21 and up; happy hour cruises are open to all ages but alcohol is only served to adults over 21.
Younger visitors tend to enjoy the Key West Aquarium and Shipwreck Treasure Museum.
Most of the top sights in the Old Town are wheelchair-accessible, though many historic homes and buildings have a secondary entrance for those with limited mobility.
From Miami, Key West is reached via a roughly 4-hour drive south along scenic US-1 highway. Keep in mind that traffic is heavy and slow on this two-lane road on weekends, holidays, and during peak tourist season. Alternatively, there is high-speed catamaran ferry service between Fort Myers and Key West that docks near Mallory Square. Key West also has a small airport, with bus and taxi service to the Historic District.
The Historic District can be visited year-round, though Key West is a popular summer destination when visitors can enjoy its beautiful architecture paired with time on the beach or cruising the coastline. Plan a spring or fall trip for cooler temperatures and more manageable crowds.
For the best bird’s-eye view over the Key West Historic District, climb the 88 iron steps to the top of the Key West Lighthouse. Built in 1825 to guide ships entering the port past hazardous reefs, the lighthouse offers sweeping views over Key West and the ocean. You can also tour the grounds to see the restored keeper’s quarters and check out the collection of nautical artifacts, antique furnishings, maps, and vintage photos.