For those enamored by destinations with a strong sense of history, it’s rewarding to find a spot where regional identity has been preserved yet the vibe still feels hip. Newport, Rhode Island, thrives on the diversity and architectural beauty it has held dear for centuries. Its cobblestone streets of galleries and boutiques offer treasures with a funky flourish. And its topographical virtue—water surrounding three sides—assures that in Newport’s restaurants, you’ll eat better than any pilgrim.

Two million people visit Newport each summer, and the town refuses to shut down, even when the cold hits. August’s Jazz Festival and February’s Winter Festival lure guests with musicians and ice sculptors, respectively. But the city’s most acclaimed event is the Newport International Boat Show. For four days in September, the harbor becomes home to sleek, hand-made sailboats and enormous hybrids, all vying for coveted prizes in innovation and design. Best of all, you get to see the city at its most beautiful time: when all the tourists have left.

Staying
The Chanler at Cliff Walk is a historic mansion with 20 refurbished, richly decorated rooms, some with private gardens and Jacuzzis. No detail is forgotten at the Chanler, no pleasure unanticipated. Its site at the start of the famed Cliff Walk means you overlook the Atlantic Ocean while breakfasting on the terrace or mingling with locals in the bar. The inn has grown so renowned that it’s not uncommon to glimpse a bride while sipping your martini.

Castle Hill Inn is a remodeled Victorian seated at the tip of a 40-acre peninsula, on the mouth of Narragansett Bay. It has that rare, secluded feeling. With its mahogany woodwork and old portraits lining the walls, you could be forgiven for thinking you’re in a favorite aunt’s house—if all her bedrooms were luxuriant. Try to obtain the Turret Suite—with its 30-foot ceiling and 360-degree view, it’s the most dramatic in town.

Dining
It seems less of a guarantee these days that travelers will find their hotel's food superior to local offerings.  How convenient, then, that the best places to stay in Newport also house its finest restaurants.

At the Chanler’s Spiced Pear, put yourself in the hands of Chef Kyle Ketchum, who gives an extra kick to sauces he mastered at Le Cordon Bleu. His dishes are artful, their flavors layered and complex. His tasting menu is a triumph. Here, I ate the perfect scallop.

Castle Hill’s genius is its freshness, from seafood to produce—much of it organic and grown by local farmers. With his Portuguese roots, Chef Jonathan Cambra brings a light Mediterranean influence to his cooking. Sit in the oval dining room surrounded by windows or, better yet, on the grassy lawn, where you can watch sailboats go by. You’ll never want to leave your chair.

Walking
Despite its reputation as a sailing capital, hoofing it is one Newport’s best forms of entertainment. The three-and-a-half-mile Cliff Walk, along the rugged coast, is the only national recreational trail to run through a historic district: the backyards of those Gilded Age mansions someone wittily dubbed “cottages” in the 19th century. While the manses may garner more press, what’s surprising about Newport is that it holds more colonial buildings than any other American city. In the heart of town, you can visit both the nation’s oldest lending library and synagogue, where George Washington gave a speech hailing religious liberty. Historical walking tours are offered daily.

Sightseeing
To understand how the great barons summered, not merely from the outside, tour their mansions. The Breakers is an Italian Renaissance-style palazzo, commissioned by Cornelius Vanderbilt, designed by Richard Morris Hunt, and built by dozens of European craftsman on 13 acres overlooking the Atlantic Ocean. Rough Point, the former home of Doris Duke, has the most stunning perch of them all, but also unrivaled is its collection of fine art, amassed over seven decades by the Duke family. Renoirs and van Dycks grace the walls of rooms filled with rare furniture, tapestries, textiles, and porcelain.

Golf & Tennis
Newport is the birthplace of tennis in America, and at the International Tennis Hall of Fame Museum, you can actually play on its 13 grass courses. This is the tournament site, dating to 1881, that went on to become the U.S. Open.

Newport National Golf Club is set on 200 acres of former farmland, bordering the Narragansett Bay and Atlantic Ocean. The Irish-style links course features greens and fairways made from seaside bent grass and fescue.

Boating
Just because the America’s Cup race left Newport in 1983, you don’t have to skip the water yourself. Chartered boats, harbor cruises, and sailing classes are all available in season (www.gonewport.com).

If Time Allows
Hike the three-perimeter trail at the Sachuest Point National Wildlife Refuge, where seals, ducks, and terns make their home. Stroll the ocean-side grounds of Salve Regina University, where students blithely throw lacrosse on one of the prettiest campuses in the country. Bike, or ride with your car windows down, along Ocean Drive, to grasp what makes Rhode Island, with its 400 miles of shoreline, such an extraordinary little state.

Details
Castle Hill Inn
www.castlehillinn.com

The Chanler at Cliff Walk
www.thechanler.com

International Tennis Hall of Fame Museum
www.tennisfame.com

JVC Jazz Festival
August 8–10, 2008
www.festivalnetwork.com

Newport Cliff Walk
www.cliffwalk.com

Newport County CVB
www.gonewport.com

Newport International Boat Show
September 11–14, 2008
www.newportboatshow.com

Newport Mansions, Preservation Society of Newport County
www.newportmansions.org

Newport National Golf Club
www.newportnational.com

Newport Winter Festival
February 13–22, 2009
www.newportevents.com/winterfest

Sachuest Point National Wildlife Refuge
www.friendsNWR-RI.org

Photo Captions:
Photo 1: Castle Hill Lighthouse has been guarding Newport’s easternmost point since 1890.
Photo 2: The Chanler is located at the start of Newport’s famous Cliff Walk and offers an excellent starting point for a tour of Newport’s historic mansions.
Photo 3: A sailing town at heart, Newport offers enthusiasts unlimited opportunities, including America’s Cup Charters, which offers the largest fleet of America’s Cup winners in the world.