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Discover New England Self-Drive
13-night self-drive visiting parts of Massachusetts, Maine, Vermont, and Rhode Island.


An anti-clockwise tour around the highlights of New England, bookended with a stay in Boston. Stop off in the Berkshires, a popular holiday haunt for Boston’s and New York’s elite since the 1800s; discover glorious mountains in New Hampshire and green scenery in Vermont; and savour stunning sea views in Newport, Rhode Island.
Itinerary overview
Highlights of trip
Boston, Massachusetts
Orientate yourself with the city by following the Freedom Trail, a series of 16 historic sights that tell Boston’s incredible story. You could also take a wander around the beautiful grounds and museums at Harvard University or catch the Red Sox in action at Fenway Park.
Built above a magnificent double-arch waterfront portico that straddles part of the historic Rowes Wharf Harbor, The Boston Harbor Hotel is in a league of its own. Check-in...
The swanky Fifteen Beacon has all the trappings of an upscale stay: the services of Clef’s d’or trained concierges, sunken jacuzzi baths and a fourth-century Italian mosaic...
It’s hard to imagine a more convenient location from which to explore historical Boston on foot, than the Hyatt Centric. Just a stone’s throw from historical Faneuil Hall, ...
Kennebunkport, Maine
Pick up your hire car and drive 100 miles north. Here, you can find a patch of the exceptionally beautiful Goose Rocks Beach to call your own, peruse the collection of streetcars at the Seashore Trolley Museum, and ride a vintage trolley. It’s a renowned foodie spot famous for its soft and cakey whoopie pies.
Bar Harbor, Maine
It might not be the fastest route to Bar Harbor, but if you follow Route 1, you’ll pass through some lovely towns like Waldoboro and Rockland and get fabulous ocean views. When you arrive, stretch your legs on Bar Harbor’s Shore Path, which provides fantastic views of the harbour and the mountains. Perhaps you’ll hike in Acadia National Park or take a whale-watching tour before returning for dinner. You’ll find everything from seafood shacks to fine-dining restaurants.
Acadia National Park. Whale-watching. Hiking and leaf-peeping. Bar Harbor sure has a lot going for it. The Holiday Inn Bar Harbor makes a super handy base for explorations.
Jackson, New Hampshire
On your drive to Jackson, you’ll cross the state border from Maine to New Hampshire for some time in the White Mountains. This is a particularly resplendent area when it's ablaze with colour in the autumn, but it's just as pretty in other months. Try canoeing deep into the scenery or following miles of hiking trails that crisscross the terrain.
Vergennes, Vermont
Take the scenic Kancamagus Highway on your drive to Vergennes, crossing into Vermont. When you arrive, there’s a small downtown area to explore. Still, most find themselves here for incredible outdoor adventures, whether you prefer hiking and biking or watery escapades like kayaking and sailing on Lake Champlain.
Stockbridge, Massachusetts
Drive south back into Massachusetts to the Berkshires, where quaint, storybook-style New England inns have a backdrop of mountains and forests. Spend your days exploring food markets, orchards, and breweries, or up the ante on ziplines and white-water rapids.
Newport, Rhode Island
Rhode Island is the smallest state in the USA by area and home to the sailing capital of New England, Newport. Orientate yourself by following the 3.5-mile Cliff Walk and looking at some of the impressive Newport Mansions from the Gilded Age.
Smugly occupying a central location on Newport’s scenic waterfront, the family-friendly Marriott is a contemporary hotel where dining with a view is a particular highlight.
This landmark hotel is one of Rhode Island’s fanciest. It oozes a sense of history and claims the best views in town.
Falmouth, Massachusetts
From your base in Falmouth, you can explore Cape Cod or even take a ferry to the gorgeous islands of Martha’s Vineyard or Nantucket for the day. You can also go whale watching, cycle the Cape Cod Rail Trail past cranberry bogs and salt marshes, or relax at the beach and enjoy the ocean breeze.
Boston, Massachusetts
Your circular tour of New England is complete when you return to Boston, a final exclamation mark on an incredible trip to a picture-perfect slice of the USA.
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