Anna Maria Island, Florida
Think of this as the vintage Florida family vacation, without the theme parks. This seven-mile-long barrier island has three distinct towns, all of them high-rise-free. At Bradenton Beach and Holmes Beach, you'll find entertainment from a simpler era — including minigolf, dolphin tours, ice cream stands, and crab races. But stay at the north end of the road, in Anna Maria village — where quiet reigns. Rent a beach bungalow through Airbnb or VRBO (a three-bedroom house with a pool goes for about $350 per night). Rent a bike — the island is crisscrossed by lanes and trails; if your legs get tired, there's a free trolley (with bike racks). After the kids have had their fun, relax for an afternoon at Bean Point, where Tampa Bay meets the Gulf of Mexico, a chilled-out stand of palm fronds and pearly white sand that's like a forgotten island in the Caribbean. It's the perfect balance: one family vacation, zero compromises.
Getting there: From Tampa, drive an hour south; from Sarasota, drive a half-hour north.