$325,000 to $500,000

Cape Charles, Virginia
Population: 1,000
Median home cost: $349,000

For most travelers on the Chesapeake Bay Bridge-Tunnel, Cape Charles merely marks the northern terminus at the tip of the Delmarva Peninsula. For the more nautically savvy, it’s also the name of a historic lighthouse guarding the entrance to Chesapeake Bay. Far fewer folks know there is a town called Cape Charles, just off Route 13 on the bay side of the peninsula.

Cape Charles once bustled as a railroad and ferry town, docking steamers and transferring railcars across the bay to Norfolk. The community tucked in for a long nap in the 1950s, and recently awoke to find that its 7-block downtown and charming store of Victorian and early-20th-century homes (you’ll find 11 Sears, Roebuck and Co. mail-order kit houses from the 1920s) have substantial allure for both natives and transplants—known locally as “come heres.” A town treasure, the historic Palace Theatre, has been restored and now presents musicals and plays. Just steps away, residents enjoy a free nightly production of a different sort: spectacular sunsets over Chesapeake Bay and the Virginia mainland beyond, with prime viewing at the town’s public beach. But Cape Charles remains a working town. Watermen still haul in the Chesapeake’s famous harvests of fish, blue crabs, and scallops. The bay is one of America’s premier sailing grounds, and the ocean side of the Delmarva has its own attractions for boaters. The Virginia Seaside Water Trail extends 100 miles from the mouth of the Chesapeake north to Chincoteague Island, near the Maryland border, meandering through the tranquil bays that separate the peninsula from a chain of barrier islands. One popular stop along the trail is Wreck Island Natural Area Preserve, an unspoiled patch of dunes and salt marshes accessible only by watercraft and prime for surf fishing in early autumn. It isn’t necessary to take to the water, though, to enjoy Cape Charles’ natural surroundings—south of town, Kiptopeke State Park offers hiking trails, a fishing pier, and a beach; the Eastern Shore of Virginia National Wildlife Refuge is adjacent.

Insider Tip
Cape Charles’ local pride is embodied in the Stage Door Gallery, staffed entirely by volunteers. It showcases the works of Eastern Shore artists and exhibits everything from stained glass to bird carvings to oil paintings.

Todos Santos, Baja California South, Mexico
Population: 4,078
Median home cost: $350,000

It’s a long way from a dusty collection of sugar mills to official status as a “magical town,” but Todos Santos has made the transition. Located on the Pacific side of the Baja Peninsula, roughly 50 miles from Cabo San Lucas, Todos Santos was founded as a mission town in 1723 and hit its sugar stride around 1850. The last sugar mill closed more than 40 years ago, and today it’s the arts scene that makes life sweet. The “magic” part has to do with the government’s designation of the town as a Pueblo Magico, one of 33 such communities in Mexico. Raising a town to this status helps emphasize its traditions and customs, and encourages appropriate development.

Todos Santos’ cachet as an arts town dates to the 1987 arrival of painter/sculptor Charles C. Stewart. More artists (and about a dozen galleries) followed, along with American and Canadian expatriates. Newcomers have helped drive development, but the town’s master plan and the ongoing restoration of historic buildings have kept growth from getting tacky and out of hand. Anyone who has an irresistible urge to visit a big-box store will have to head down to Cabo.

Official or not, Todos Santos’ setting is magical. The town stands between the Sierra de la Laguna mountains and the Pacific, and the old sugar fields have been replaced by ranches, vegetable farms, and papaya and mango orchards. Residents can choose from five beaches in and around the town, four of which offer terrific surfing. At Playa Punta Lobos, beachgoers enjoy watching local fishermen return with their catch in the early afternoon. Another gift of the Pacific: a salubrious summer climate, with temperatures around 10 degrees cooler than at other Baja locations.

Would-be expats should be aware that Mexican law forbids foreign ownership of real estate within some 30 miles of the nation’s coasts. The legal work-around is called a fideicomiso, where a local bank holds the title in trust and the “buyer” is beneficiary, with the right to sell the property and benefit from the proceeds.

Insider Tip
Mexico has responded to its growing population of immigrant retirees by granting them senior benefits. The Instituto Nacional de las Personas Adultas Mayores (INAPAM) can provide you with a card that offers discounts on medical and transportation services (including airfare); restaurants, museums, and entertainment; construction materials; even dry cleaning. (You must have a valid residence visa.)

Naples, Florida
Population: 21,162
Median home cost: $380,000 (can reach much higher)

Naples represents such a slew of superlatives—Golf Capital of the World, Number One Small Art Town in America, home to one of the top 20 beaches in the nation—that it’s reasonable to wonder if it can possibly live up to its billing. But residents have nearly 90 championship golf courses in and around town, no fewer than 134 art galleries, a philharmonic orchestra, and 10 miles of snowy white sand rimming the crescent bay that reminded early planners of Italy. And if all that isn’t enough, consider the fact that hundreds of America’s most-discerning and hype-proof business barons—many of them Fortune 500 CEOs—have taken up residence in this Gulf-side gem.

But Naples isn’t all exclusive enclaves—in fact, most communities here aren’t gated, and home prices are as varied as the highly individual neighborhoods that make up the municipal area. There’s a lively downtown, Old Naples, where replicated Georgian and French Colonial styles dominate. The big draw here is the Fifth Avenue and Third Street South shopping districts, with antiques emporia, high-fashion boutiques, and fine-art galleries. Other shopping districts range from the waterfront Tin City, specializing in antiques and local crafts, to The Village on Venetian Bay, where the Italian theme continues, this time with an Adriatic motif. Nor is recreation in and around town simply a matter of tee times with the rich and famous. Naples offers proximity to Everglades National Park, Big Cypress National Preserve, the Florida Panther and Ten Thousand Islands National Wildlife refuges, Picayune Strand State Forest, and great fishing in mangrove estuaries as well as offshore. Close at hand is the Audubon Corkscrew Swamp Sanctuary, with 11,000 pristine acres threaded by a 2¼-mile-long boardwalk. Unspoiled natural surroundings are such an integral part of Naples’ outskirts that renowned nature photographer Clyde Butcher maintains a studio in the Everglades, where the Big Cypress Gallery retails his black-and-white prints. A city of superlatives? It’s surprising that even more “bests” and “mosts” haven’t been bestowed on Naples.

Newburyport, Massachusetts
Population: 17,465
Median home cost: $385,500

Newburyport, Massachusetts, an old port city at the mouth of the Merrimack River, has enjoyed three golden eras. The first came during the post-Revolutionary period of the 1790s, when wealthy merchants and sea captains began to build elegant Federal mansions lining High Street and lesser thoroughfares in the city’s south end. Newburyport’s next stab at maritime glory came in the 1830s, when ships laden with Far Eastern goods sailed into the harbor. But for more than a century afterward, despite some local manufacturing, the little city sank into economic obscurity so dismal that hardly anyone could afford to tear anything down. That set the stage for Newburyport’s great revival, beginning in the early 1970s, when adventurous types from Boston and beyond began snapping up and restoring antique commercial and residential stock at bargain-basement prices.

For close to 40 years now, Newburyport has been one of the great success stories of the New England coast. Its first generation of restorer-entrepreneurs has since sold to succeeding waves of folks who are more than happy to commute to high-tech jobs along Route 128, and even 40 miles south to Boston, especially now that passenger rail service has been revived. Not that Newburyport is a period-piece bedroom community. Its compact downtown, still centered around those redbrick 1811 commercial blocks of Market Square, contains shops, taverns, and trendy restaurants. The waterfront, with its boardwalk promenade, harbors a mix of pleasure craft and working fishing vessels.

Natural splendor surrounds Newburyport’s doorstep. Much of the terrain to the west and south consists of pristine salt marshes protected by strict Massachusetts law, and Plum Island lies across a narrow causeway. That barrier island’s northern extreme is dense with year-round and vacation homes, but most of it holds the Parker River National Wildlife Refuge, a realm of dunes, maritime forest, and gorgeous ocean beach, which is rarely crowded because of the refuge’s limited parking. Northwest of town, Maudslay State Park’s hiking and cross-country skiing trails lace through a lovely wooded property along the banks of the Merrimack.

Over the past few years, the town’s overheated housing market has cooled, but no one expects another 100-year hibernation. All in all, Newburyport is a great place to wait for your ship to come in.

Gibsons, British Columbia
Population: 3,931
Median home cost: $400,000

British Columbia’s Sunshine Coast is an anomaly in a region famous for drizzle. This 110-mile stretch along the mainland side of the Strait of Georgia—the scenic inside passage—is blessed with good weather. Gibsons lies at the southern end of this deeply indented coastline, just a 40-minute ferry ride from Vancouver across Howe Sound. Gibsons is a split-level community. Lower Gibsons recalls its origins as a fishing village, with a fleet of trollers and gill netters that served the hungry piers of Vancouver. Commercial boats still fish from the town wharf (you can often buy fresh seafood dockside), but they now share space with picturesque shops, cafés, and restaurants. The Landing was the setting for the Canadian Broadcasting Corporation’s 1971 to 1990 TV program “The Beachcombers,” which put the town on the map—at least for Canadians. Molly’s Reach, which served as the show’s sound stage, has since been converted to a café. A walkway that begins in this quaint neighborhood follows the shoreline from Armours Beach, popular with swimmers and windsurfers, to the marina.

Upper Gibsons isn’t quite so quaint. Perched in a hillier portion of town farther from the water, it offers supermarkets, shopping malls, and fast food. But no place in Gibsons, no matter how functional, is far from the outdoor splendors that have made the Sunshine Coast attractive to Canadians from as far away as the Atlantic Provinces. This corner of British Columbia is the country’s equivalent of Southern California—or at least what Southern California has long represented to Americans. Places for soaking up the coast’s famous sunshine and lovely scenery include Secret Beach, a pebbly strand at the bottom of a long flight of steps; Soames Hill, with great mountain and water vistas; and many miles of footpaths and bike trails. Opportunities for wildlife-viewing abound—the Strait is home to seals, sea lions, and orcas, and birders can spot migrant as well as resident bald eagles.

Folks in this southwestern corner of British Columbia obviously place a premium on the Sunshine Coast. On that ferry across Howe Sound, you only pay a fare heading to Gibsons. The trip back to Vancouver is free.

Insider Tip
No trip to Gibsons would be complete without a visit to shop the “Gumboot Nation” of Roberts Creek, named after the favored footwear of British Columbia fishermen. Be sure to visit the gallery of the world-renowned Inside Passage School of Fine Woodworking, have an ice cream at Roberts Creek General Store or a cold beer at Royal Canadian Legion Branch #219, and take home a souvenir from Elements Local Arts & Eco-Ware. The Gumboot Garden Restaurant serves delicious Thai chicken.