The Kennedys, the Bushes, the Obamas … Taylor Swift — the upper crust has always flocked to New England for its swanky seaside attractions and adorable rural retreats. Good news: You don’t need to have a famous name to find a good time. Thanks to an influx of fashion-forward shops, farm-fresh food and cozy-cool hotels, a vacation here is just the right mix of serenity and style.
Newport, Rhode Island
Newport is known for world-class sailing, historic mansions and the legends of the Gilded Age. Dive into history at the Grace Vanderbilt, a 33-room boutique hotel, originally built in 1720. Today, the luxurious property features expansive suites, an indoor and outdoor pool, evening piano music, and a rooftop with stunning views.
Just steps away is Bowen’s Wharf, a lively waterfront collection of restaurants, bars and shops. Fluke serves well-executed dishes that leave clichés behind, while The Mooring is a go-to for some of the city’s best seafood. The Black Pearl is an institution: If clam chowder and drinks on a floating dock are your thing, welcome to nirvana.
Experience the city’s standout activity with an unforgettable sail on the Schooner Madeleine, or view the seas on a motorized yacht like the 1929 Rum Runner II.
Newport’s fairytale mansions are a must-see. The Breakers, with its 70 rooms, is considered the crown jewel, while the Rosecliff is a Hollywood favorite — The Great Gatsby and 27 Dresses both filmed here.
Every year, more and more Miamians flock to scenic Maine. The seaside city of Portland happens to be one of the hottest foodie destinations in the country.
James Beard-nominated Duck Fat serves sandwiches and fries (yes, made in duck fat) that you’ll never forget. Trendy Eventide Oyster Co. is the place to head for abundant raw bar and a buzzing night scene. The town’s best lobster roll is a matter of high debate, but J’s Oyster is our pick, and the laid-back, seaside setting is an all-around delight. For a lobster break, head to tiny Vietnamese noodle spot Cong Tu Bot; the pho is truly expert-level.
James Beard-nominated Duck Fat serves sandwiches and fries (yes, made in duck fat) that you’ll never forget.
Art and fashion coincide in Portland. Explore unique, artisanal works like the sand-made jewelry of Beachdashery or the local photography, pottery and more at Lisa-Marie’s.
Martha’s Vineyard and Cape Cod, Massachusetts
Martha’s Vineyard and Cape Cod embody New England coastal imagery: shingled exteriors, preppy residents and quaint walking towns.
If you’re looking for unspoiled, dune-filled beaches, head straight to the Cape. Stay at one of two deluxe resorts, both of which boast a loyal, year-after-year clientele: The 100-year-old oceanfront Chatham Bars Inn is as iconic as it gets, with its sand-washed brick exterior, private beach and refined restaurants; the elegant Wequassett Resort & Golf Club, on a quiet, sailboat-dotted bay, is great for families. The Wequassett’s Twenty-Eight Atlantic restaurant is one of the most acclaimed on the Cape, thanks to enchanting dishes like the fluke crudo — balanced by sweet local watermelon and a zippy vinaigrette.
The Vineyard is nothing if not distinguished, from its Kennedy history to its constant crop of Hollywood visitors. Take advantage of the off-season in bustling Edgartown. Stay at the sprawling, idyllic Winnetu Oceanside Resort, a perfect location for surfing and beaching. Nearby, the historic Charlotte Inn houses The Terrace restaurant, where chef Justin Melnick expertly applies French techniques to New England classics.
Dive into dinner at renowned State Road, which has hooked numerous presidents with its consummate farm-to-table cuisine. The stone fireplace and high ceilings create a beautiful palette for creative dishes like hearty biscuits and bone marrow.
If “cozy luxury” were a hotel category in New England, Winvian Farm would define it.
Before he married Amy Schumer, Chris Fischer was a chef at Beach Plum Inn, a favorite of the Obamas. Try breakfast here; specifically, the local fish cakes with poached eggs. In preparation for your trip, check out supermodel Garrett Neff’s much-loved Katama Swim, a uniform that fits well in its eponymous island town.
New England’s lush countryside, with its covered bridges and rolling hills, is truly magical. The picturesque region of Litchfield is dripping in charm and upscale surprises — no wonder Diane von Furstenberg lives nearby.
When the president and vice president of Manolo Blahnik buy a house and a farm in the country, it must be something special. Arethusa Farm now boasts a prize-winning dairy, critically acclaimed restaurant al tavolo, a beloved coffee shop and two stores. “Litchfield offers us a special kind of solitude from the craziness of our Manhattan lives,” the couple, George Malkemus and Anthony Yurgaitis, said. “It’s a paradise.”
If “cozy luxury” were a hotel category in New England, Winvian Farm would define it. The woodsy, 113-acre property is home to 18 private cottages, each designed by a different architect. The five-star restaurant, serene spa, and activities like snow-shoeing and biking entertain guests all year.
Stay or dine at the exclusive Mayflower Inn & Spa (where the Real Housewives of New York recently vacationed), overlooking acres of old-English gardens. And hit the hotel’s Tap Room for cocktails and live music.
Visit downtown Litchfield for a store you’ll never want to leave: Oliphant Design. Eclectic, sophisticated housewares live alongside on-trend jewelry and Florida-ready resort wear.
If You Go: New England Hotels, Restaurants and Shops
Grace Vanderbilt: gracehotels.com/vanderbilt
Bowen’s Wharf: bowenswharf.com
The Mooring: mooringrestaurant.com
Black Pearl: blackpearlnewport.com
Schooner Madeleine and Rum Runner II: cruisenewport.com
The Breakers and Rosecliff: newportmansions.com
Duck Fat: duckfat.com
Eventide Oyster Co.: eventideoysterco.com
J’s Oyster: jsoysterportland.com
Cong Tu Bot: congtubot.com
Chatham Bars Inn: chathambarsinn.com
Wequassett Resort & Golf Club and Twenty-Eight Atlantic: wequassett.com
Winnetu Oceanside Resort: winnetu.com
Charlotte Inn and The Terrace: thecharlotteinn.com
State Road: stateroadrestaurant.com
Beach Plum Inn: beachpluminn.com
Katama Swim: katamaswim.com
Arethusa Farm: arethusafarm.com
al tavolo: arethusaaltavolo.com
Winvian Farm: winvian.com
Mayflower Inn & Spa and Tap Room: gracehotels.com/mayflower
Oliphant Design: oliphantdesign.com