Key West is small enough that you'll need little more than a comfortable pair of walking shoes (or perhaps a bike) to take in most everything the city has to offer. To start, 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.

Key West is surrounded by clear, azure waters, but its beaches are unremarkable on the Florida Beach-O-Meter (a fate shared by Keys beaches as a whole). Because the reef prevents waves from crashing ashore and forming sand, the natural shoreline is relatively rough and spotted with chunks of coral. Some beaches have been "renourished" with sand imported from the Bahamas. But in most cases, the sand is dingy beige, and seaweed laces the shoreline. Beneath the water, sea grasses, though harmless, make the water appear less than crystal clear. A good pair of sandals or water shoes can save your feet when you enter the water.

With a reef fronting the Keys on the Atlantic side, Key West makes a good base for snorkeling or diving excursions. You'll need to take a boat trip to see anything worthwhile. In addition to stingrays, lobster, nurse sharks, yellowtail, moray eels, huge brain corals, sea turtles and all kinds of other sea life, there are several shipwrecks in the area.