The best way to get the lay of the land in Old Town is to take the Conch Train Tour, in which you can get the fascinating history of the whole area. You’ll learn of Southernmost point, and you can have your picture taken by the Mile Marker 0 sign at the end of Whitehead Street. Take a look at Hemingway House where Ernest “Papa” Hemingway lived in the 1930’s.
Other attractions include Fort Zachary State Park, Key West Lighthouse, Mallory Square (complete with sunset tightrope walkers), The Green Parrot Bar, and you can learn about the spooky side of Key West on the Ghost Tour!