The Most Relaxing Weekend Trips From Boston

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New England charm awaits on these five luxurious weekend trips from Boston

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From the Back Bay to the North End to Harvard Square, Boston is a city with no shortage of weekend activities. There are an endless number of lobster rolls to try—served either Maine-style or Connecticut-style—hit shows that frequent the Boston Opera House, and no fewer than 217 city parks in Boston proper. However, outside the city limits, the rest of New England offers so much in the way of history, outdoor exploration, and varying levels of commitment to either whole-belly fried clams or maple syrup production, depending on which direction you drive from Boston. These are the most relaxing and luxurious weekend trips from Boston: 

Nantucket, Massachusetts


Terri Pommett/Courtesy The Wauwinet

Nantucket is 30 miles off the coast of Cape Cod, and yet, so easy to get to. Take a short ferry ride from Hyannis, and you’ll be on island in an hour. In true coastal New England fashion, you must take in the views from a lighthouse while on Nantucket: visit Great Point Lighthouse, Brand Point Lighthouse, or Sankaty Head Light. Rent bikes at Nantucket Bike Shop and leisurely pedal to Sconset Beach, near to Sankaty Head Light, and the Sconset Beach Bluff Walk, a charming walking path that takes you along the coast and by quaint Nantucket cottages. Pro tip: grab some ice cream from the Sconset farmer’s market. Of course, a seafood dinner with a view is practically mandatory on island, so dine at Cru, known for their phenomenal raw bar selection. If you’re up for a post-beach drink, stop in at Cisco Brewers for live music and a sampling of Cisco beers, wines from Nantucket Vineyards, and spirits from Triple Eight Distillery. As for luxury accommodations, stay at The Nantucket Hotel, home to The Nantucket Club & Spa, or The Wauwinet, an American Express Fine Hotels & Resorts partner and Nantucket’s only Relais & Châteaux property.

The Berkshires, Massachusetts


Courtesy Canyon Ranch Lenox

The Berkshires is often associated with a fall getaway in New England, but the reality is, it’s an area worth visiting in any season. Hiking possibilities abound in The Berkshires, but start at Beartown State Forest on the Pond Trail loop, or at Monument Mountain Reservation. Visit one of the oldest botanical gardens in the U.S., Berkshire Botanical, or for a taste of the historic homes of western Massachusetts, visitors can even follow the Berkshire 18th Century Trail to six masterfully preserved homes each holding approximately 200 years of history. Stay in Lenox at Canyon Ranch Lenox, an American Express Fine Hotels & Resorts partner, for a Berkshires wellness retreat. You can sign up for specific spa treatments or wellness packages (from weight loss to partner programs) ahead of your arrival to maximize your self-care while at Canyon Ranch. Spending time in Lenox must involve a trip to Tanglewood, a live music venue and the summer home of the Boston Symphony Orchestra since the ‘30s. To complete a perfect summer evening in The Berkshires, dine on the porch at Firefly, or grab one of the 28 seats at Nudel, serving one of the most elegant and innovative seasonal menus in western Massachusetts, primarily inspired by and utilizing local ingredients.

Barnard, Vermont


Courtesy Twin Farms

Drive two and a half hours from Boston and you’ll arrive at the American Express Fine Hotels & Resorts property Twin Farms, an adults-only, food-focused inclusive resort set on more than 300 acres. Your weekend at Twin Farms is all about outdoor activities (think: hiking, biking, kayaking, and canoeing) and tailored meals. Off property, visitors can fish, swim, or skate at Silver Lake Park, or head to the championship golf courses in Quechee or Woodstock. You can also visit Fable Farm—where much of the produce served at Twin Farms is grown—or head to Norwich to take a baking class at King Arthur Flour. The artistically inclined, after fawning over the art collection at Twin Farms, can head to Simon Pearce Gallery, a gallery featuring glass-blown home goods and hand-crafted pottery. The resort will even set up a private shopping experience for you. Round out your weekend in Barnard with a trip to Long Trail Brewing Co. before returning to Twin Farms to dine in the Main House by candlelight.

Chatham, Massachusetts


Courtesy Chatham Bars and Inn

You can’t debate a weekend trip from Boston without at least considering Cape Cod. Life on the Cape slows down, especially as compared to the bustle of Boston. Get involved with the seafood culture of Cape Cod with an oyster harvesting experience with the Chatham Shellfish Company, or rent kayaks and canoes at Bass River Kayaks. If you’d rather stay on dry land, bike into town—rent bikes at Chatham Hood Bikes—to explore the town’s shops and art galleries along Main Street, popping in at Struna Art Galleries and Chatham Fine Art. For a luxurious meal in Chatham, we love Twenty-Eight Atlantic or Impudent Oyster for dinner—both have exceptional views and fresh seafood, though be warned, seating at Impudent Oyster is first come, first serve. To round out a classic Chatham evening, either catch a flick at the Orpheum Theatre, which opened in 1916, or grab a drink at the Chatham Squire. As accommodations on the Cape go, stay at Chatham Bars Inn Resort & Spa, another American Express Fine Hotels & Resorts partner. Arguably the most relaxing venue on Cape Cod, it’s home to The Spa at Chatham Bars and a glorious pool and hot tub with adjacent cabanas. 

Newport, Rhode Island


Courtesy Marriott

One of the easiest weekend getaways from Boston, Newport offers the perfect beachside locale for Bostonians in need of a quick escape. Stay at the Newport Marriott, which sits moments away from Newport’s celebrated attractions and features sweeping, waterfront views. Or take up residence at Castle Hill Inn, an American Express Fine Hotels & Resorts partner, in one of their luxe beach cottages, perched on a stretch of private beach. Tour the Newport mansions as you amble along the famed Cliff Walk, and visit the Newport Art Museum, founded in 1912. On Saturday night, dine at Bouchon Restaurant & Inn, known for their French fare, then see the Rhode Island Philharmonic Orchestra. On Sunday, head to The Lawn at Castle Hill Inn for Sunday brunch overlooking the Atlantic Ocean, and take some sun at Easton’s Beach before heading home.