Key West is so small that you'll need little more than a comfortable pair of walking shoes (or perhaps a bike) to soak up most everything the city has to offer. To start out, you may want to get the lay of the land by hopping on the Conch Tour Train or the Old Town Trolley -- both will take you past virtually every point of interest on the island. (The Conch Train is nonstop, while the Trolley has nine hop-on/hop-off points.)

Most of the sights are located in Old Town, where you'll find ginger breaded Victorian homes and charming bed-and-breakfasts commingling with packed bars and countless souvenir shops. The main drag is Duval Street, which is crammed with restaurants, galleries and shops. Duval is a good landmark to use to figure out where you are and where you're going. The southeastern end of the street is near the Southernmost Point (a requisite photo op for all visitors).

From there, you can stroll north on Whitehead Street, which passes several popular attractions. These include the Ernest Hemingway Home and Museum and the Key West Lighthouse. Farther north are the historic Audubon House and the Mel Fisher Museum (artifacts recovered by the famous underwater treasure hunter). At the far-northern end of Whitehead, you'll find Mallory Square, home of the not-to-be-missed sunset celebration. Head a few blocks east of Duval to explore the Key West Cemetery, a must-see collection of aboveground graves that capture the island's quirky character.