Marco Island, Florida

Fans of San Marco Island in Florida contend it’s a one-in-a-million resort. And while it’s a hardy boast, there’s no arguing it’s at least one in ten thousand.

That’s because San Marco is part of the Ten Thousand Islands chain. It is the largest and only developed island in the group, located off the southwest coast in the Gulf of Mexico.

This stretch of Florida that includes San Marco is called Paradise Coast, aptly named for its natural beauty. San Marco, a 24-square-mile barrier island sandwiched between the Gulf and mangrove-lined estuaries, is carved with 100 miles of canals. The attractions are on and off-shore. When not dining, shopping or playing golf, locals flock to the white sand beaches and parks full of wildlife. Some 200 species of birds keep birdwatchers endlessly captivated. Boating and fishing are a way of life here. San Marco is also a jumping-off point for shelling. Beaches and sandbars on some of the nearby barrier islands make for some of the best shelling around.

For most of its history, San Marco was remote, mosquito-infested and sparsely populated. Residents relied on ferry service to access the mainland and, later in the 1930s, a wooden, hand-operated swing bridge to accommodate vehicular traffic. Modern development would begin in the 1960s when three brothers—Elliot, Robert and Frank Jr. Mackle—paid $7 million for virtually the whole island and carried out their vision to turn San Marco into an affluent resort for leisure living. Today, the year-round population tops 15,000 and more than doubles with seasonal residents in winter.

The real estate vibe is contemporary coastal luxury, no surprise given that waterfront properties are a large share of the market. Exclusive communities throughout the island offer high rise condominiums, ready-to-build parcels and private estates, some with private boat docks.