The tiny island 10 miles off Maine is home to about 60 residents, who love living in a place so remote that medical care comes via helicopter. Three ferry companies operate in the summer from Port Clyde, New Harbor and Boothbay Harbor. Once on land, you can stroll to where you're staying—just toss your luggage onto your inn's baggage truck. One of the most scenic B&Bs is The Island Inn, on a bluff over the harbor, from $130. There are plenty of things you can't do here: Cell phone service is iffy, Wi-Fi is nonexistent and bikes are banned from the more than 17 miles of hiking trails. What is plentiful, however, are the birding opportunities on a Puffin Watch cruise.
Best Travel Back in Time Getaway
When the sounds of the Chautauqua Symphony reach your inn's porch, it's time to stroll over to the amphitheater for a few hours of Mozart or ballet. Cars have never been allowed in the town, which was designed as a walkable community just outside Jamestown. At its heart is the historic Chautauqua Institution, an education center that's only open in the summer, with workshops by the likes of Garry Trudeau and Joyce Carol Oates. Try The Maple Inn, from $80. The genteel haven has 750 acres of lawns, a lake and a daily farmers market. Until last year, alcohol was also a no-no, so people sipped it out of teacups and called it "Chautauqua tea." Even though the ban is over, residents still sit on their front porches and drink their evening cocktails out of teacups.
Best Day-Trip Getaway
Bald Head Island, N.C.
Bald Head has a rowdy past as a pirate hideout, but the island has since become a vacation haven. Over 80 percent of the island's 12,000 acres is conservation land. The Bald Head Island Conservancy leads nature hikes and special walks to sea-turtle nesting sites.
Best Historical Getaway
Tangier Island, Va.
The three-mile-long island in the center of the Chesapeake Bay feels like a world of its own. Residents—who speak with a distinctive Cockneyish accent—navigate the narrow lanes either on golf carts or on bikes to visit neighbors and chat over the ubiquitous white picket fences. The new Tangier History Museum provides a closer look at island life, including Tangier's role in the War of 1812, when British forces used it as a staging ground. Complimentary kayaks are available for paddling along the water trails. Or try your hand catching peeler crabs on an overnight Honorary Waterman's Tour.
Best Art Getaway
Halibut Cove, Alaska
The boardwalk along Halibut Cove, about six miles from Homer, is lined with stores and art galleries, and more than half of the 23 residents are artists. But there's nothing snooty about this scene—the artists often mingle with out-of-towners at Nardelli's, the cove's floating espresso bar. Halibut Cove is part of Kachemak Bay State Park, so there's plenty of wildlife to view, including humpback whales. As the name implies, Halibut Cove is a popular fishing spot, too. Accommodations are expensive, so your best bet is to stay in Homer, a 30-minute Danny J ferry ride across the bay. "When the tide is low, you can walk pretty far out and dig for your own shellfish," says Dawn Schneider, general manager of the Land's End Resort, where all 114 rooms have private balconies, from $79.