The town of Boca Grande on Gasparilla Island is like Palm Beach without the bling: pastel cottages, Gulf-front estates, and a nice assortment of upscale but understated shops and restaurants. Duponts, Vanderbilts, and other elite visitors have been vacationing here since the Gasparilla Inn opened in 1913. At this low-key but stylish retreat, almost everyone dresses smart-casual, favoring colorful Florida looks such as Lilly Pulitzer and Vera Bradley.
People generally get around by bicycle or golf cart to check out the 1890 lighthouse/museum at the island's southern end or the gorgeous length of sand that stretches along its entire Gulf shore. In the sleepy off-season, beachgoers can spend an entire day without seeing anyone else until locals walk their dogs at sunset.
Shoppers stop at Ruhama's Books in the Sand to buy a beach read or some souvenir sand dollar note cards. Anglers will find a flotilla of boats in Boca Grande Pass when the tarpon are running; the rest of the year, fly-fishing yields snook and other prized fish.
Stay: The Anchor Inn has four quiet suites and a pool. Rates start at $195; anchorinnbocagrande.com. The larger Gasparilla Inn includes 61 rooms and suites, plus an additional 78 bedrooms in surrounding cottages. Rates start at $375; the-gasparilla-inn.com.
Eat: The Temptation Restaurant & Bar lives up to its name with palate-pleasing dishes including bronzed grouper over sauteed Brussels sprouts in an orange beurre blanc; temptationbocagrande.com. The garden patio at 3rd Street Cafe is the perfect backdrop for the restaurant's Mediterranean-inspired dishes; 941/946-0155. Hudson's Grocery (look for the flamingo-pink gas pump) stocks gourmet picnic fixings, barbecued ribs, and cold beer; 941/964-2621.