...Trip idea

New England Exploration

Weave your way through New England on a road trip loop that takes in coastal towns, cultural stops, historical sites, wilderness trails and some of America’s best hotels.


  • Enjoy the open road and the freedom of a self-drive holiday
  • Discover the East Coast’s best museums including Mass MOCA and the Norman Rockwell Museum
  • Stay at some of America’s most highly regarded hotels such as the Four Seasons and Twin Farms
  • Get a taste of New England at exquisite farm-to-table restaurants and harbour-side seafood feasts
  • Go big on experience – cruise on an antique yacht, go fishing and kayaking and hike the Green Mountains

Whether you’re an art aficionado, love the freedom of a road trip or simply want to explore the variety of New England, this nine-day itinerary covers a wide diversity of activity, landscapes and culture. From leading museums to charming seaside towns, luxe hotels to historic settlements, this East Coast exploration is an enchanting way to get to know New England.


This nine-day itinerary sees you driving around the coast and inland New England, bedding down at four luxury hotels.


Start in Boston, with stops in Rhode Island and The Berkshires before looping up to explore Vermont.

When to go:

We’d recommend the warmer months from June; plus New England is spectacular in the Fall from mid-September when the colours of the turning leaves set the landscapes alight

Boston, Massachusetts, USA Downtown Skyline
Skyline and inner harbour including Rowes Wharf at dawn, Boston,
Harvard Uni USA
Boston Statue USA


Arriving in Boston, you can immerse yourself immediately into this fascinating city, full of cultural institutions including Harvard, founded in 1636 and known for being America’s most prestigious Ivy League school. Take a guided tour, learning the intricacies of Boston and a must is a visit to the Museum of Fine Art (MFA), one of the world’s most comprehensive art museums with a wing focused on Art of the Americas with American art from ancient to modern. Take a turn of the two-mile Freedom Trail, with stops at museums, churches, a ship, and other historic markers which will enlighten you on the history of the American Revolution.

Four Seasons Hotel Boston

Overlooking Boston’s historic Public Garden, the Four Seasons Hotel Boston is perfectly placed to enjoy the doorstep attractions of Boston, in particular the walking trails and boutique shopping in Newbury Street. As you would expect with a Four Seasons, the rooms come furnished to a high standard – the suites are especially roomy with views over the gold-domed State House. On the eighth floor, you’ll find a fabulous lap pool and fitness facilities and the outdoor Sanctuary restaurant is a cosy place to dine after a day exploring.

Newport, Rhode Island
Sail boat USA
lobster_trap_fisherman USA
Sailboat sailing towards the horizon
Castle Hill Lighthouse, Newport, Rhode Island (RI)
Coastal Home in Newport, Rhode Island
A blue whale breaching out of the ocean
Female hiker enjoying the view from Beehive Trail in Acadia
Ocean House USA
Ocean House USAcabanas
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Ocean House USA club_room

Rhode Island

Your road trip will start properly today as you pick up your hire car and hit the road! Head to Rhode Island where for the next few days, you’ll enjoy its 400 miles of coastline dotted with white-sand beaches, historic buildings, exclusive residences and art galleries. Newport, with its yacht-filled harbour, is where you’ll steer out to sea for a cruise on an antique motor yacht in the waters of the Narragansett Bay. Dock at a harbour for a chef-prepared gourmet lunch, gaze at the famous oceanfront Newport mansions and have a spot of fishing off Prudence Island. You will also get a chance to visit Jamestown, one of America’s oldest settlements.

Ocean House

Perched high on the bluffs of Watch Hill, Ocean House is an iconic New England seaside resort. Overlooking the crashing surf, this hotel epitomises New England coastal chic, with a smart décor throughout with sophisticated suites and cottages providing an extremely comfortable stay. The spectacular beach lures guests outside plus onsite there is croquet, art classes, jazz brunches and classic lobster boils.

Autumn in New England (Pepperell, MA)
Tanglewood Music Center in Autumn, Lenox, Massachusetts
Wheatleigh Hotel USA  Hi_LW1719_49900960_Exterior
Wheatleigh Hotel USA  Hi_LW1719_36146297_LW1719_pool_Wheatleigh
Wheatleigh Hotel USA  LW1719_47160666_Aviary
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Wheatleigh Hotel USA  Hi_LW1719_38549598_Winecellar
Wheatleigh Hotel USA  Hi_LW1719_31619291_Dining Room
Wheatleigh Hotel USA  Hi_LW1719_31619275_May 2010 19

The Berkshires

From Rhode Island you will drive west for over two hours to Lenox in Massachusetts, a hilly region in the heart of The Berkshires known for its famous dance and arts programs like the Tanglewood music festival. Take your time exploring this interesting town – don’t miss leading art experiences such as the Mass MOCA and the Norman Rockwell museum; the former is one of the largest centres for contemporary art and performing arts in the US and the latter a homage to America’s favourite illustrator of American culture. Lenox is also the place to experience farm-to-table food – be sure to enjoy a relaxed dinner tasting the finest produce of the area in surprisingly upmarket surroundings.

Wheatleigh Hotel

Clasped in 22 acres of pristine lakes and rolling mountains, Wheatleigh Hotel is a peaceful place to relax for a few days. Inspired by his ancestral family home in Wheatley, Oxfordshire, Henry H. Cook purchased estate land in 1893 and developed Wheatleigh into an Italianate-style country home. Today it is a scene of chic refinement with manicured lawns, an outdoor pool, tennis courts and an impressive wine cellar. Suites are airy with high ceilings and original art on the walls, while the French gastronomic restaurant is found in the colonnaded Portico dining room.

Barn in Vermont country side surrounded by autumn trees
Sunset at Kent Pond, Killington VT
Montpelier town skyline at autumn in Vermont, USA
Twin Farms USA _MG_1738
Twin Farms USA TF Chef’s Table-13
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Twin Farms USA log_cabin_exterior
Twin Farms USA JW_orchard_bed
Twin Farms USA JW_aviary_hot_tub_dusk_final
Twin Farms USA CS17_Meadow Bedroom
Twin Farms USA CS17_Meadow Bathroom
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As you turn your sights toward the north of New England, you’ll pass through small artisan towns and the beautiful landscapes of Vermont. You may also see Vermont’s famous covered bridges, there are over 100 of them and they were constructed around 1820 – a cutesy reminder of New England’s heritage traditions. Enjoy gorgeous views of the Green Mountains, which are always green from its tall pine trees, even in winter. The peaks can be traversed on the Long Trail, a wilderness hiking route that will take you through forests, up and around boulders and beside shimmering lakes. Drink in the views before you need to think about your return journey home and the end of your road trip.

Twin Farms

It’s fitting that the end of your itinerary coincides with, in our opinion, one of the best hotels of your trip. A rustic-luxe sanctuary, the hotel is surrounded by 300 acres of pine forests and is big on outdoor experience - hike through the invigorating landscapes, canoe or swim in the pond, or head out to the hills with a gourmet picnic. The Bridge House Spa is the place to relax afterwards with its glass brick steam room and Japanese furo. Twin Farms’ cottages with their stone tub jacuzzis, flickering fires and views deep into the forests are the perfect place to round off the day.


After nine days driving around enjoying the highlights of New England, you’ll feel enlightened about this interesting part of the world which combines fascinating American history,  a deep-seated cultural program from modern art to musical performances and spectacular nature from cool coastal hangouts to the lofty mountaintops of Vermont.

Sarah Ward Hedges

Personal Travel Designer

01488 689700 Read Sarah’s profile
"While many associate road trips in the US with California, I highly recommend this New England itinerary, which has the perfect mix of coast, culture and mountains."

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