Miles from Naples: 59
The northern half of the Sanibel-Captiva island duo, Captiva was once a pirates’ lair and now yields vacation gold. Quiet beaches, beautiful seaside homes (many for rent), shells galore, and the fieriest sunsets on Florida’s west coast make the case for unplugging and basking in barefoot luxury.
STAY: Captiva Island is known for its exclusive seclusion, but Sea Oats takes “hidden” a step more clandestine (seaoatscaptivaisland.com). With its front yard the bay and private shared beach access on the other side, this vacation home feels miles and smiles away from the daily grind. Multigenerational families and groups of up to 30 can stay together, yet have their individual space. Choose from one of seven lavish bedrooms in the main house, or take a step into old island style in the two-bedroom guest house.
Families also gravitate to South Seas Island Resort (southseas.com) on the island’s northern tip, which offers accommodation in villas, cottages, private homes, and hotel rooms. The appeal of South Seas is its village-like atmosphere with multiple dining options, shopping, and just about every activity under the sun.
EAT: Captiva House restaurant at ’Tween Waters Inn (tween-waters.com) is one of the island’s best. The seafood here is second to none (don’t miss the lobster spaghetti), and the gulf-front location yields perfect sunset views. For a more casual, if kitschy, experience, head to the Bubble Room (bubbleroomrestaurant.com). The best thing on the menu is dessert—the cakes are stacked nearly a foot high—but most people come to marvel at the vintage decor and the Christmas bubble lights that give this landmark its name.
SEE + DO: At Sea Oats, request kayaks and paddleboards for exploring Buck Island, a wildlife preserve 10 minutes across the bay channel. At South Seas, check out Ambu Yoga (ambuyoga.com) for mindful classes in studio, on the beach, or on paddleboards. The Sanibel Sea School (sanibelseaschool.org) offers field-based ocean education and guided tours by land or boat.
DON’T MISS: Shelling is big in Captiva; visit iloveshelling.com for a primer and comb the beaches for 250 species of shells.