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 hamlet (there are lots where you can leave yours), 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 (800/836-2787, ciweb.org). Its website lists the lodging options, including The Maple Inn (716/357-4583, themapleinn.com, 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. –Ann Hood See photo
North Captiva Island
A four-mile-long crescent off southwestern Florida, North Captiva Island has an exclusive feel and a simple soul. Visitors arrive hauling a week's worth of groceries and then disappear into rented beach houses in the scrubby, coquina-shell-covered landscape. "You get so busy doing nothing that you forget what you came here for," says Kristie Anders, a year-round resident who boats to work on neighboring Sanibel Island.
North Captiva was once part of larger Captiva Island until storms in the 1920s severed the landmass. Families, honeymooners, and sand castles dot the public beach, but walk far enough into Cayo Costa State Park and the beach is all yours. Dolphins frolic close to shore, and gopher tortoises burrow in the sand.
Part of the beauty of the island is that there are no hotels. You can book a beach house through the North Captiva Island Club Resort (800/576-7343, northcaptiva.com, from $1,200 for a week). Island Girl Charters operates ferries from Pine Island, near Fort Myers (islandgirlcharters.org, $37 round trip). –Rachael Jackson See photo
Michigan's Lake Shore Road, along the perimeter of Mackinac (ma-ki-nah), is the only state highway that doesn't allow cars. Yet it's still busy on summer days: Tandem bikes and horse-drawn carriages, including some fringe-topped surreys, create a symphony of spinning wheels, clomping hooves, and dinging bells. The route is one of the main draws for visitors because of its views of Lake Huron and the Straits of Mackinac.
Other attractions include Fort Mackinac, built by the British in 1780 (mackinacparks.com, $10), and the pricey Grand Hotel, the setting for Somewhere in Time. The hotel charges nonguests $15 just to set foot inside, but you can gawk from the front lawn for free (800/334-7263, grandhotel.com). There are other places to stay, anyhow. The Harbour View Inn has pillared porches and plenty of floral prints (906/847-0101, harbourviewinn.com, from $129). Save room for a box of fudge from Murdick's, the most popular souvenir on the island (906/847-3530, $14 per pound). It's the reason locals call tourists "fudgies." –Susan Stellin See photo
The five-square-mile speck is an active fishing community, and evidence of the islanders' livelihood is everywhere. The daily ferry to Ewell (410/425-2771, smithislandcruises.com, $24 round trip) docks right by Ruke's Seafood Deck, known for its crab cakes (410/425-2311, from $8). Nearby, the Smith Island Cultural Center displays tools of the crabbing trade (smithisland.org, $2.50).
In the town of Tylerton, accessible only by boat, women pick crabmeat from their husbands' haul to sell at the Smith Island Crabmeat Co-op (410/968-1344). If you're not ready to rejoin civilization in Ewell, the Inn of Silent Music overlooks the sound (410/425-3541, innofsilentmusic.com, from $110).
The Smith Island Cake was declared Maryland's state dessert in April. "The goal is to have lots and lots of layers," says Beverly Guy, who sells her 10-tier cake at the Bayside Restaurant (410/425-2771, slice $3.50). –Andrea Sachs See photo
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 (Monhegan Boat Line, 207/372-8848, monheganboat.com, $30 round trip), New Harbor (Hardy Boat Cruises, 800/278-3346, hardyboat.com, $30 round trip), and Boothbay Harbor (Balmy Days Cruises, 800/298-2284, balmydayscruises.com, $32 round trip)
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 (207/596-0371, islandinnmonhegan.com, 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 (hardyboat.com, $22). The island has inspired many artists, including Rockwell Kent. To see some of his best work, stop by the Monhegan Museum, next to the lighthouse (monheganmuseum.org, $4). –Sarah Mahoney See photo
The car is king in California, but golf carts rule the streets of this island an hour by Catalina Express ferry from Long Beach (800/481-3470, catalinaexpress.com, $60 round trip). Rent your own golf cart through Island Rentals (310/510-1456, $80 for three hours) and do the loop up to the Wrigley Memorial & Botanical Garden, landscaped with native plants (310/510-2595, $5). Carts aren't allowed in the interior, where 200 buffalo roam, but Discovery Tours offers trips to the region (310/510-8687, $72).
Follow the crowds to Original Jack's Country Kitchen for breakfast, lunch, or dinner: The Portuguese-bread French toast is a standout (310/510-1308, $6). Big Olaf's (310/510-0798, scoop $2) is a popular ice cream parlor down the street from the art deco Avalon Theatre (310/510-0179, movie $8).
Since 1896, the Hermosa Hotel has had the cheapest lodging on the island (877/453-1313, hermosahotel.com, from $45). Away from Main Street's bustle, the hilltop Zane Grey Pueblo Hotel is where the author of The Lone Star Ranger wrote more than 80 books (800/378-3256, zanegreypueblohotel.com, from $65). –Brian Wilson See photo
Bald Head Island
Bald Head has a rowdy past as a pirate hideout, but the island has since become a vacation-home haven. Old Baldy, as the island's lighthouse is often called, was what inspired Jeff and Tonya Swearingen to first visit Bald Head. Last year, they bought a second home there. "We love having no cars and having the woods next to the beach," says Tonya.
The island also welcomes plenty of day-trippers, who fill up the ferry from Southport (910/457-5003, baldheadisland.com, $15 round trip). Lodging options include a few B&Bs, such as the Marsh Harbour Inn (910/454-0495, marshharbourinn.com, from $190), and beach-house rentals (800/432-7368, baldheadisland.com, from $135).
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 (910/457-0089, bhic.org, from $7). –Diane Daniel See photo
The guy across from you at the backwoods bar could be a Fortune 500 CEO or a shrimper fresh from a day at sea. That's life on this small wooded isle about 45 minutes by ferry from Hilton Head Island (843/341-4870, daufuskiefrontporch.com, $30 round trip). Golf carts are the only form of transportation, available through the Daufuskie Island Resort (800/648-6778, daufuskieislandresort.com, rooms from $169). The resort's plantation-style mansion and oceanfront cottages are spread across 1,200 of the island's 5,000 acres.
What makes Daufuskie Island unique is its Gullah population. They're descendants of African slaves who brought with them such traditions as sweetgrass basket weaving; baskets and other local art are on display at the Daufuskie Gallery (843/842-3300, daufuskiegallery.com). The gallery is among the few modern developments (there are also two golf courses) on an island that doesn't change much. The live-and-let-live vibe is on full display at Marshside Mama's, which serves a delicious low-country gumbo to whoever traipses in—locals, visitors, even the occasional dog (843/785-4755, from $9). –Jennifer Wilson See photo
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 (gotangierisland.com). Complimentary kayaks are available for paddling along the water trails. Or try your hand catching peeler crabs on an overnight Honorary Waterman's Tour (757/891-2331, $175 with lodging).
Ferries to Tangier are operated out of Reedville, Va., by Tangier & Chesapeake Cruises (804/453-2628, tangiercruise.com, $25 round trip) and out of Crisfield, Md., by Tangier Island Cruises (410/968-2338, tangierislandcruises.com, $25 round trip). –Jeanine Barone See photo
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. Homer Ocean Charters leads tours of the bay (800/426-6212, homerocean.com, half-day trips from $105). As the name implies, Halibut Cove is a popular fishing spot, too. The guides at North Country Halibut Charters can show you the ropes (800/770-7620, northcountrycharters.com, from $190).
Accommodations are expensive in Halibut Cove, so your best bet is to stay in Homer, a 30-minute Danny J ferry ride across the bay (800/478-7847, $50 round trip). "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 (800/478-0400, lands-end-resort.com, from $79). –Beth Collins See photo