Nicknamed the “City by the Sea,” Newport is often celebrated as the first resort town in the nation, and prides itself on traditionally WASPy pastimes: sailing and tennis, of course. Indeed, it’s heralded as the “sailing capital of America,” and Newport’s history as a yachting paradise is deeply tied to its decades hosting the America’s Cup—a visit to the town is incomplete without an afternoon at sea. It doesn’t hurt that Newport’s architecture is perhaps best viewed by boat. The town itself is perched at the tip of Aquidneck Island, and many of the historic homes were built to face the water, which was the only method of approach before the Newport Pell Bridge was constructed in 1969. Aside from a mansion tour, visitors can also try the 3.5-mile Cliff Walk, which winds along the coast, behind the expansive lawns of Gilded Mansions overlooking the sea. 

Other Newport highlights include sunset cocktails on the sprawling lawn at Castle Hill and a visit to the International Tennis Hall of Fame, where guests can dine at La Forge overlooking the grass courts. Head to the historic downtown and stroll the cobblestone streets along Thames Street before grabbing a mudslide at the Black Pearl and enjoying dinner at the Clarke Cooke House—try for a reservation at Sky Bar, on the third floor, but remember to pack a jacket and tie (the formal dress code is still firmly in the Gilded Age). 

The recently redesigned Hotel Viking is the oldest hotel in town; it opened in May 1926 to accommodate overflow houseguests of summer residents. (Early investors included William H. Vanderbilt, and it was once referred to as “Newport’s living room.”) Stay in the former bedrooms of the Gilded elite at The Vanderbilt, the 1909 mansion built by Alfred Gwynne Vanderbilt. Gardiner House is a newer entry to the luxury hotel market; it was founded by Newport summer residents inspired by the sumptuous interiors of their own family cottage, The Ledges.

Newport wasn’t the only seaside town drawing wealthy seasonal residents in the 19th century. Further down the coast, Westerly established itself as a less flashy summer alternative. The completion of the Stonington Railroad in 1837 ushered in vacationers from New York and Boston, as did the Watch Hill Inn, which opened its doors in 1845. After the hotel’s debut, wealthy families migrated to the scenic bluffs of this rugged Rhode Island peninsula to build Victorian summer homes. While Westerly may not ring an immediate bell for readers, its two coastal villages, Weekapaug and Watch Hill, should sound familiar—particularly the latter, as it’s the location of Taylor Swift’s famed Rhode Island residence (and the falsely rumored locale for her wedding). Another integral location for the wedding-that-didn’t-happen is the Ocean House, a gloriously opulent yellow-shingled mansion that first opened in 1868 and persists as the social spot for vacationers today. 

Watch Hill was named for its role as a lookout in the French and Indian War, and those views remain celebrated today, though for less militaristic purposes. Sunbathe at Misquamicut State Beach, or embark on a nature walk at Winnapaug Pond before retiring to the Olympia Tea Room, a local favorite, for dinner. Nearby Weekapaug is significantly more low-key and secluded, with unspoiled nature and wondrous seasonal gardens. Check out the Weekapaug Inn, an 1899 estate perched along Quonochontaug Pond, for farm-to-table cuisine and classic coastal elegance.

Block Island is beloved for its bucolic rolling hills, grand Victorian architecture and quintessential New England charm. The island first established itself as a summer destination in 1852, with the opening of the Spring House Hotel, the first on-island accommodation marketed toward outside visitors. Over the next few decades, a small number of tourists began arriving by sea, but it wasn’t until the Old Harbor breakwater was completed in 1875, creating a sheltered port for ferries and other vessels, that the vacation economy flourished and stately Victorian hotels welcomed the Gilded Age summer traveler. 

Block Island remains popular with seasoned summer residents and day-trippers alike. A perfect Block Island summer day is spent biking along scenic coastal roads, hiking the winding trails of Clay Head Preserve, sunbathing or surfing along the pristine shores of Mansion Beach, and enjoying sunset cocktails from the scenic vantage above the towering, 150-foot Mohegan Bluffs. Stay at the Sullivan House, a boutique property built in 1904, with sweeping ocean views from the majestic wraparound porch.

Directly across the water from Newport, Jamestown is a majestic resort town on Conanicut Island, offering sweeping ocean views and a dramatic rocky coast. It became popular as a summer community with the creation of the steam-powered ferry service from Newport in 1873, and provides a more serene setting for sailing and dockside cocktails than its sister resort town across the water. The idyllic Beavertail State Park ensures that the island retains its rural charm, while Beavertail Lighthouse is as picturesque as any of the oft-photographed lighthouses on the (far more crowded) island of Nantucket. 

And yet, even if Jamestown prides itself on being less snobby than Newport, it certainly is just as WASPy (and conveniently close via boat or the Pell Bridge to the bustling bars along Thames Street). No less a bard of coastal splendor than James Taylor owns a summer home on Jamestown’s southeastern shore, frequently boating across the bay to appear at the Newport Folk Festival. Check out the Portuguese cuisine at Sunset Beach Oyster Bar and order the mussels at JB’s on the Water. Stay in town at the quaint East Bay Bed and Breakfast or the recently renovated Victorian beach cottage, Lionel Champlin Guest House. Better yet: splurge for a rental to truly experience a taste of island life.

For a more relaxed surfer vibe, head across the water from Jamestown to nearby Narragansett, named after the Native American community that resided along its shores. This is for those looking to hang ten. The town developed as a summer resort in the mid-19th century, when Joseph Heatly Dulles, an affluent businessman from Pennsylvania, visited the region in 1848 and then rented seasonal homes for friends and family the following summer. The opening of the Narragansett House in 1856 catered to his larger network of friends from Philadelphia and New York, and the construction of the 1876 railroad to Narragansett Pier solidified the destination as a top Gilded Age summer resort.

Today, the coastal town is famed for its wide stretch of sand along Narragansett Town Beach and the iconic stone Towers of Narragansett. Spend a day surfing and sunbathing, and check out the impressive collection of rock cairns along Black Point Trail near Point Judith. In the late afternoon, retire to The Coast Guard House at sunset to enjoy the best lobster roll in the state of Rhode Island (and I’ve tested many). The Shore House is a historic 31-key boutique hotel originally built as a private residence in 1901; enjoy a cocktail and sweeping views of the Atlantic from the wraparound porch. Another option is The Break Hotel, a 16-room property with a heated saltwater pool and retro-chic decor.

Head north to Little Compton to experience true pastoral seaside splendor. One of the last true hidden gems along the Rhode Island coast, Sakonnet’s name derives from the Indigenous Sakonnet people (a band of the Wampanoag nation) who resided in the area. The town first attracted summer visitors in the 1850s, as seasonal residents began lodging with local families on coastal farms. In the 1880s, the first dedicated summer residences were constructed on scenic Warren’s Point, and steamships from Providence began ferrying visitors to Sakonnet Point. The town has retained its small-town charm, fighting overdevelopment with a “Little Compton, Let’s Keep it Little” campaign in the mid-20th century, passing two-acre zoning in 1986, founding the state’s first land trust in 1972, and establishing the Agricultural Conservancy Trust in 1985.

The coastal farming town has preserved its heritage with endless options for farm-to-table cuisine from local planters available from Wishing Stone Farm, or at roadside stands. The town doesn’t have a single traffic light (forget the Bellevue standstill on summer rush hour in Newport), but it does have peaceful, pristine beaches. Check out the historic Wilbor House Museum for a slice of Little Compton history, and peruse the fresh produce at Wishing Stone Farm. Head to Art Cafe for your morning coffee, and be sure to grab an ice cream cone at Gray’s, a perennially popular summer activity. Little Compton is one of the last if-you-know-you-know destinations in New England, and its privacy and serenity are fiercely guarded by locals and summer residents alike. As such, the housing options are limited for visitors, and renting a summer cottage is truly your best bet for an extended stay. If you’d rather stay at a hotel, check out the Stone House Inn, a regal estate constructed as a private home in 1854, with 16 guest rooms near Sakonnet Point.