Conch Tour Train leaves from 303 Front St. in Mallory Square. Step into a canary yellow open-air car shaded by striped awnings for a 90-minute, 14-mile tour through old and new Key West. Knowledgeable “engineers” regale passengers with humorous yet informative anecdotes about the island's colorful history, architecture and local legends, including a story about a wealthy cigar manufacturer who moved his house across the street via mules because he didn't care for the way the sun hit it. You'll also hear tales about Ernest Hemingway, Harry Truman, and the Navy's role in Key West history.
During the tour, the train passes by many local landmarks, including City Cemetery, Duval Street, the Ernest Hemingway Home and Museum, the Key West Lighthouse Museum, the Little White House Museum, Smathers Beach, and the Southernmost Point. The tour also takes you off the beaten path through residential areas populated with pretty pastel-colored, gingerbread-trimmed Victorian houses surrounded by lush gardens. Take note of the shops and restaurants you'll see along the way; you'll want to check them out later.
The train makes a 10-minute stop midway through the tour at its depot at the junction of Front and Duval streets, where you can purchase refreshments. The train also stops during the trip at Flagler Station at the Historic Seaport and at the intersection of Duval and Truman streets. You may disembark at any of the stops and hop back on later to resume the tour.