Since the town of Key West is only 2 miles wide and 4 miles long, getting around is easy. You can take either the ninety-minute Conch Tour Train (305-294-5161, www.conchtourtrain.com), which allows you to get on and off at nine stops along the way, or the Old Town Trolley Tour (305-296-6688, www.historictours.com), which for $25 per person takes you on a tour through the neighborhoods as friendly guides point out over 100 sights while telling tales of pirates, rumrunners, and famous ancestors drawn to a city. Or you can rent bikes from the Bicycle Center (305-294-4556) or Key West Bicycle Rentals (305-296-3344) and make it a family affair. And, of course, a town of this size is also small enough to walk.

Best Time to Go

Since Key West lies in the tropics, there's not much difference in its climate throughout the year. As with other tropical destinations, the rainy season occurs in summer, making the air more humid, although there are sea breezes to cool things off. Year-round temperatures hover between 80° and 90°.

Cautions and Safety Concerns

Being such a small place, Key West is generally safe. About your only concern should be how long you stay out in the sun and whether you're wearing enough sunscreen.