Snorkeling at Fort Zachary Taylor State Park. RELATED LINKS City Guide Key West Take the Beach IQ Quiz Watch Beach Videos

Although Key West might appear to have all the makings of a great beach vacation—a breezy tropical climate, offshore coral reefs and warm turquoise waters on all sides—the island has surprisingly few nice beaches, and none that compare with some of the more appealing stretches of coastline on the Florida mainland. Much of the sand on Key West shores is imported, and the island’s coastline has suffered occasional outbreaks of E. coli contamination due to aging and overloaded waste treatment facilities.

That doesn’t necessarily mean you should avoid the beaches altogether, but in the interest of setting realistic expectations, think of Key West more as a historical and cultural destination, or as a lively base for boating, fishing and diving excursions well offshore.

Smather’s Beach, Key West’s longest strand, extends along the southern coastline near the airport—far from idyllic, but suitable for sun worshippers and windsurfers. South Beach, near the west end, is more convenient to Old Town hotels and guesthouses. Just around the bend at Fort Zachary Taylor State Park is an appealing stretch of sand most locals regard as Key West’s finest beach. Bring snorkeling gear and a picnic, and take some time to explore the fort itself, a 19^th-century citadel that kept Key West out of Confederate hands for the duration of the Civil War.