The heart of Key West is the historic Old Town area, which runs from White Street west to the waterfront. In the early 19th century, wharves, warehouses, chandleries, ship-repair facilities, and the U.S. Customs House sprang up around the deep harbor to accommodate large vessels -- both commercial ships and those of the U.S. navy. The lavish Victorian houses the town's wealthy merchants and sea captains built, along with the dwellings of famous writers, artists, and politicians who've come to Key West over the past 175 years, are among the area's approximately 3,000 historic structures. Old Town also has the city's finest restaurants and hotels, lively street life, and popular nightspots. Take a taxi, rent a bicycle or moped, walk, or take a shuttle to get around, as parking is scarce and costly.

The Overseas Highway splits as it enters Key West, the two forks rejoining to encircle New Town, the area east of White Street to Cow Key Channel. The southern fork runs along the shore as South Roosevelt Boulevard (Route A1A), past municipal beaches, salt ponds, and Key West International Airport. Along the north shore, North Roosevelt Boulevard (U.S. 1) passes the Key West Welcome Center, shopping centers, chain hotels, and fast-food eateries.