ON THE WATERFRONT

From its pre-colonial roots to its opulent turn-of-the-century mansions, Newport, Rhode Island, is a city that embraces its history. On any given day, at any given stop, visitors may find themselves in one of the oldest spots in America—be it a tavern, a library, or a house of worship. Yet despite Newport’s well-seasoned cred (380 years of it, to be exact), the sailing capital of the world remains remarkably young at heart, and uniquely adept at breathing new life into its generations-old foundations. From its fine dining to yachting, stylish people-watching, and a nightlife scene designed for the 21st century (because nobody parties like it’s 1639 anymore), this vibrant seaside community offers something for everyone, even beyond peak tourist season.

The Vanderbilt
41 Mary St.
401-846-6200

Originally built in 1909 by railroad tycoon and ill-fated Lusitania passenger Alfred Gwynne Vanderbilt, this mansion turned boutique hotel features oversize fireplaces, tufted armchairs, a professionally curated lobby gallery, and countless other Gilded Age charms. Check out the bespoke experiences on offer—from glass-blowing classes to vintage-auto rentals—and then dine poolside in the relaxing garden terrace. At the end of the evening, head up to the roof-deck for an unbeatable view of Newport Harbor.

The Chanler at Cliff Walk
117 Memorial Blvd.
401-847-1300

No trip to Newport would be complete without an amble up to Cliff Walk to take in a combination of geographical and architectural marvels. The quickest way to get there? Rent a room right smack-dab in the heart of it. Originally the summer retreat of US Rep. John Winthrop Chanler and Margaret Astor Ward, this reimagined 19th-century “cottage” (a term that greatly understates things, but a little modesty is fine) offers elegance with a European touch, from its manicured gardens to its private terraces. Ask about the French Provincial or Victorian Manor Rooms, or splurge on a secluded ocean villa, with its own private outdoor hot tub and sauna.

SkyBar at Clarke Cooke House
26 Bannister’s Wharf
401-849-2900

White Horse Tavern
26 Marlborough St.
401-849-3600

This spot, the oldest bar in America, predates US independence by more than a century. Originally constructed in 1652 as a private residence and converted into a tavern in 1673, the White Horse has had its share of faithful regulars and colorful owners; the colonial General Assembly held meetings here, and one of its innkeepers, William Mayes, was also a pirate who plundered ships on the Red Sea. Given that history, you’d expect some strong spirits, but today the tavern is better known for its extensive wine collection, which has earned it Wine Spectator’s Award of Excellence many years running.

IYAC Newport
536 Thames St.
401-841-5250

The International Yacht and Athletic Club serves the saltiest dogs in town when it’s not hosting an annual around-the-island race. At the bar, stand shoulder to shoulder with dockworkers, fishermen, America’s Cup competitors, and others who make sure this club is their first stop when they reach dry land. Remember: This is a lifestyle, not a theme, so everything here is authentic, from the sea stories to the Dark ’n Stormy cocktails, appropriately heavy on Gosling’s Black Seal Rum.

International Tennis Hall of Fame
194 Bellevue Ave.
401-849-3990

The ITHF holds its enshrinement weekend annually in late July, honoring the latest inductees and hosting the ATP tour’s Hall of Fame Open on their pristine grass courts. But the hall is worth a visit year-round for the 25,000 objects in the museum’s permanent collection. Current exhibits include Courting Fashion, a digital curation of iconic tennis style, from Stan Smith’s eponymous shoe to Björn Borg’s Wimbledon pinstripes to Serena Williams’ black lace at the 2010 US Open, and Tins, Cans, & Cartons, a survey of over 600 tennis ball containers from the 1880s to today. Another highlight: a holographic Roger Federer that serves, volleys, and talks to guests.

Antique Yacht Collection
31 Bowen’s Wharf
401-678-6740

12 Meter Charters
12 Bowen’s Wharf
401-851-1216

IYRS School of Technology and Trades
449 Thames St.
401-848-5777

Newport is a sailing town—that much should be pretty obvious by now—but all local on-the-water experiences are not created equal. The key to a memorable nautical outing is to ignore the siren song of touristy boat trips and chart a course for something more authentic.

For a private charter suitable for families and small groups, check out the Antique Yacht Collection, which offers a variety of timing and time-of-day options. You can’t go wrong with a sunset cruise on the Temma, a classic 42-foot passenger motorboat. Cruise the bay, take in the unique views of Rose Island and the Newport bridge, and pop the cork on your complimentary bottle of prosecco.

For the more adventurous, 12 Meter Charters offers guided access to legit monohull racing yachts. Grind the winches and trim the sheets or—if you don’t know your mainsail from your jib—let the professionals do it for you while you daydream about competing in the America’s Cup.

For a newfound appreciation of the skilled craftspeople and technicians who design and build the vessels dotting the harbor, tour the 3-acre campus of the IYRS School of Technology and Trades. Watch students restore a fleet of classics, including the Coronet, a wooden schooner from 1885, or attend the annual summer gala in July.

Bellevue Avenue Mansions
424 Bellevue Ave.
401-847-1000

When locals ask if you’ve been to “The Avenue,” they’re referring to Bellevue, a 2.5-mile stretch of Gilded Age opulence and home to historic mansions once owned by the Astors (that’s Beechwood, now owned by Larry Ellison) and the Vanderbilts (Marble House). Our pick, however, is Rosecliff, completed in 1902 and modeled after the Grand Trianon, the garden retreat of French kings at Versailles. In 1974, the mansion served as a filming location for The Great Gatsby, directed by Jack Clayton and starring Robert Redford and Mia Farrow, with costume design by none other than Ralph Lauren. As an unexpected nexus of Jazz Age style and Hollywood glamor, Rosecliff is a timeless favorite.

Green Animals Topiary Garden
380 Cory’s Lane, Portsmouth
401-847-1000