The best way to see Key West is aboard the Old Town Trolley and Conch Tour Trains. The hour-long ride takes you all around the important sites of Key West, including the Hemingway House, Southernmost Point of the U.S., Harry Truman Little White House, and Duvall Street. The trolley/train covers over 14 miles of old Key West and is narrated with entertaining stories about the city. Walking or biking the back streets Key West are also a good way to tour the small city. An organized tour is not really necessary to enjoy Key West, but the Trolley/Conch Train is certainly entertaining!
Cruise ships can dock near Mallory Square, the most important park in Key West, or at nearby Truman Annex. All of the shops, restaurants, and bars on Duval Street and Whitehead Street are within easy walking distance of the ships. Key West is certainly an easy port of call for cruise passengers to navigate. The Truman Little White House and the tourist trams were both within easy walking distance from Mallory Square.