St. Augustine, Fla.
Where to eat: My favorite restaurant is The Tasting Room (904-810-2400, www.tastetapas.com), a lively wine and tapas spot, with live music every night, in the heart of the historic district. Its worth the 10-minute drive to Caps on the Water (904-824-8794, www.capsonthewater.com), a casual seafood restaurant and raw bar on the Intracoastal Waterway, where you can wander along the shore after dinner.
Where to sleep: Victorian House Bed & Breakfast (904-824-5214,www.victorianhousebnb.com) is a steal at $99 to $139 per night for a room with a queen bed in the historic district; suites are more.
Other tips: The weather in north Florida is different from locales farther south, and winter weather is unpredictable; temperatures can dip into freezing overnight. While theres always a threat of a hurricane in the fall, it may be the best time to visit, since temperatures are still warm but the air is not unbearably humid, as it is throughout the summer.
— Brooke Lea Foster