Just a block from Mallory Square is the redbrick terra-cotta Custom House, which houses the Key West Museum of Art & History. The landmark building was the government center during Key West’s lucrative shipwrecking era, when it was the richest city, per capita, in the United States. Visitors can stand in the very room where U.S. officials made the decision to go to war with Spain after the sinking of the USS Maine battleship—a perfect prep for the jolt of eclectic, electric experiences that Key West has in store.
Within walking distance of the Custom House, historic attractions, homes, and gardens continue to tell the story of Key West’s unusual past. The architecture is an intriguing mix of Victorian mansions and brightly hued gingerbread cottages, many of which have been transformed into museums or bed-and-breakfasts, thanks to the efforts of local foundations.
Key West’s most famous residence is the Ernest Hemingway Home and Museum, now an interactive museum for literary enthusiasts. From 1931 to 1940, the Nobel Prize-winning author lived in this Spanish-colonial-style estate, where he enjoyed some of his most productive years. In fact, many Key Westerners appear as characters in Hemingway’s novel To Have and Have Not. Today, visitors can tiptoe up the stairs to see Hemingway’s office. His desk, chair, typewriter, and wall ornaments are supposedly just as the celebrated eccentric author left them. As many as 60 descendants of his beloved cat Snowball still lounge around the tropical grounds.
The Audubon House and Tropical Gardens is an elegant mid-19th-century example of American classic-revival architecture. The home was built by Captain John H. Geiger, Key West’s first state-licensed harbor pilot. Geiger made his fortune as a master wrecker, salvaging ships that floundered on the key’s treacherous reefs. Now the house provides a perfect setting for the original works of John James Audubon, the world-renowned ornithologist, who visited the Florida Keys in 1832. While painting in the property’s tropical gardens, Audubon identified and drew 22 species of Florida birds.
The waters around Key West once claimed one ship per week on average, the remnants of which can be found at several local museums. The Mel Fisher Maritime Museum is a repository of the richest collection of 17th-century sunken booty in the Western Hemisphere. It’s also a hub for the excavation and preservation of nautical artifacts, with an emphasis on early Caribbean history and the Florida Keys.
More treasures recovered from these wrecks are on display at the Key West Shipwreck Museum, which has been modeled after the warehouse of 19th-century master wrecker Asa Tift. A must-see here: original cargo from the most profitable wreck in Key West history, the 137-foot-long Isaac Allerton, which sank in 1856.
Artists and wreckers weren’t the only ones who found sanctuary on Key West. Former president Harry Truman also caught “Keys Disease.” Immediately after World War II, he turned a former naval base into his vacation headquarters and used it as a winter home for the remainder of his time in office. Now a landmark, the Harry S. Truman Little White House is a living museum where government functions and meetings are held to this day.
To sit back, relax, and tour the port town’s highlights, choose between Old Town Trolley Tours and the Conch Tour Train; both have depots in Mallory Square. The Old Town Trolley, which touts itself as “the attraction that takes you to the attractions,” offers a 90-minute narrated tour covering some 100 points of interest. The Conch Tour Train, rolling since 1958, features wisecracking guides who provide a signature “conch’s-eye view” of the attractions. A special one-hour nonstop tour is a great way for cruise guests to make the most of the day in port. Both tours head down Duval Street to what is likely the most photographed site in Key West: a concrete monument marking the southernmost point of the United States. Who wouldn’t want a picture taken with the enormous buoy that marks a spot that’s closer to Cuba than to the U.S. mainland?
Visitors can acquire a different sense of Key West’s former residents at the oddly amusing Southern Keys Cemetery. Above-ground granite crypts are joined by headstones etched with epitaphs such as “I told you I was sick” and “At least I know where he’s sleeping tonight.”