Walk through the oldest district in Key West, admiring the many historical landmarks and hearing stories about the town’s sometimes notorious past.
After walking from the pier, you will soon arrive in the heart of Key West’s historic district, where you will find many of the city’s landmarks and learn about their significance. When Ponce de Leon first saw the key in 1521, he called it Cayo Hueso, which means Bone Island, a reference to its exposed bleached limestone foundation.
After joining the United States in 1822, Key West soon took advantage of its shallow reefs to develop industries such as salvaging, sponging and salt manufacturing. By the mid-1800s, Key West was America’s wealthiest city per capita.
As you stroll the leafy streets of Old Town, the guide will point out highlights and regale you with stories about Key West’s intriguing past. You might see Fort Zachary Taylor, a National Historic Landmark that played an important role in the Civil War and Spanish-American War, and the Harry Truman Little White House, where the president wintered.
Among the best-known residents was Ernest Hemingway, whose home is now a museum. Naturalist John James Audubon also lived in Key West in the 1830s and his residence is also a museum. Then there is Mallory Square, the city’s legendary gathering place, especially at sunset. Key West is also known for it