• Introduction
• 1. Islands with Natural Beauty
• 2. Island Beach Retreats
• 3. Grand Island Hotels
• 4. Historic Islands
• 5. Mediterranean Islands

Historic Islands

The vivid past is never too far away at these outposts, an atmospheric bunch rife with legends, artifacts, and customs.

NANTUCKET, MASSACHUSETTS
Nothing less than the former whaling capital of the world could pack as much historical punch as Nantucket. Narrow cobblestone streets wind past rows of lovingly maintained buildings, from the clapboard homes of former sea captains (in one of 12 “approved” colors) to boutiques and galleries housed in pre–Civil War structures. At the Whaling Museum, which occupies a former candle factory, examine the skeleton of a sperm whale and intricate scrimshaw carvings. After a day at the beach (they’re all accessible to the public on Nantucket), relax at The White Elephant (from $600/night; whiteelephanthotel.com), a 53-room harborside landmark that has been setting the standard for Nantucket elegance since the 1920s. Getting There: Take a ferry from Hyannis, Mass., or fly from most major New England cities.

NAGS HEAD, NORTH CAROLINA

Legend has it that Blackbeard roamed the waters off Nags Head, and pirates walked the beach at night with lanterns, causing countless ships to run aground. In the 1800s, locals salvaged lumber from these shipwrecks and built Queen Anne–style cottages (nine of which still stand). By 1903, the buzz of the Wright Brothers’ airplane engines at Kitty Hawk (five miles north of Nags Head) sparked an influx of visitors to the island’s great beaches. The 1930s-era First Colony Inn (from $159/night; firstcolonyinn.com) boasts prime beachfront. Getting There: Drive 80 miles south from Norfolk, Va., and cross the Wright Memorial Bridge into Kitty Hawk.

CATALINA ISLAND, CALIFORNIA

This storied outpost has played host to everyone from Spanish missionaries to Hollywood golden age royalty to William Wrigley Jr., who bought the island in 1919 and then built a replica Wrigley Field where his Chicago Cubs could train in spring. Catalina’s rugged interior, where buffalo and wild boar roam, contrasts with the main harbor town of Avalon, where a cylindrical Art Deco casino perches on the harbor’s lip and golf carts are the preferred mode of transport. The refined Hotel Metropole (from $199/night; hotel-metropole.com) offers oceanside-chic interiors and water views. Getting There: Take a ferry from Long Beach, Newport Beach, Marina del Rey, San Pedro, or Dana Point, or take a helicopter from San Pedro or Long Beach, Calif.

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