Located just off of Florida’s southwestern shore, Captiva Island, whose name, according to local legend, is derived from the days when the pirate captain Jose Gaspar held female prisoners there for ransom, is a second-home destination for many famous people as well as the year-round home for artist Robert Rauschenberg. At the resort, there’s almost a dizzying array of lodging options from guest rooms and cottages to private villas and rental homes. One of our members, who raved about the resort because the whole experience was “totally low-key,” recommends the Harbourside Waterview rooms as their proximity to the water makes them prime spots for dolphin-watching. Other popular activities also revolve around the sea (the island is, after all, located in the Gulf of Mexico) and include kayaking among mangroves, manatee watching (in the spring, summer and fall), paddle-boating, parasailing and going on dolphin tours.

Tip: Our member also recommends dining at one of the great restaurants outside the resort compound or going to the grocery store for food as hotel food was a disappointment. Rates based on availability (and can thus fluctuate anytime) though Harbourside rooms go for about $399 in March.