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This circular self drive holiday begins and ends in Boston, following a spectacular route that makes it's way through some of the most beautiful scenery in America. Spend time exploring the historical and atmospheric towns and villages of New England and enjoy the many walking trails and outdoor persuits of the stunning Acadia National Park, the White Mountains and the Berkshires.

Delve into the charms of Cape Cod and the old town splendour of Rhode Island's Newport. Taste the delicious clam chowder and freshly caught seafood, be enchanted by the famous covered bridges and feel the warmth of New England hospitality.


Day 1 & 2: Boston

Arrive in Boston and head to your hotel after collecting your rental car. Then head off to explore this fantastic city where cobbled streets and modern architecture blend amidst the leafy parks, artisanal markets and historic harbour. Discover the landmarks along the Freedom Trail, step aboard a catamaran to watch the whales and dine in the trendy restaurants or try the wide variety of popular food trucks and tuck in, as you absorb Boston’s rhythm.

Day 3: Kennebunkport

Depart Boston and head north, travelling along picturesque coastal beaches and stunning seascapes. Stop at Salem, to discover more about the infamous witch trials and take in the charming atmosphere and historic buildings of Portsmouth and Hampshire. End the day in the literary and artistic town of Kennebunkport.

Day 4 & 5: Bar Harbor

Drive along the beautiful coast of Maine to the town of Bar Harbor, the perfect base from which to explore Acadia National Park and the many trails of Cadilac Mountain or perhaps drive to the summit for spectacular views.

Day 6: White Mountains

As you drive inland, take in the impressive views of pristine forests and mountain ranges, as you travel towards the White Mountains, known as the rooftop of New England. This area is dotted with covered bridges that are synonymous with new England.

Day 7: Stowe

The journey continues along the White Mountains and through Lyndonville and Greensboro before arriving in Stowe. With breathtaking views, Stowe offers an abundance of outdoor activities and small-town charm, so it's sure to be a memorable stop.

Day 8: The Berkshires

Heading south, Route 100 enjoys the stunning landscapes of Vermont’s Green Mountains, pretty villages, and famous covered bridges. Spend the rest of the day and overnight in the beautiful and popular Berkshires region, where outdoor activities are plentiful and a farm-to-table food scene is sure to serve up hearty and delicious cuisine.

Day 9: Newport

Continuing south, through a number of charming towns, you may like to stop at the Hancock Shaker Village, a living history museum that brings the shaker story to life. Arrive in Newport Rhode Island and explore this vibrant city. Wonder the decadent halls of the Gilded Age mansions, enjoy the seaside lookouts on the cliff walk or simply enjoy the atmosphere and many wonderful eateries on offer.

Day 10 & 11: Cape Cod

Next, head along the coast to Cape Cod where a host of wild and beautiful beaches, picturesque towns, endless walking trails and freshly caught seafood from a multitude of restaurants ensures there is plenty to see and do.

Day 12: Boston

The final stretch of the journey takes you back to Boston along the coastal road for those last impressive views of the Atlantic coast, before dropping the car at the airport and catching the flight home.

Enquire about our Incredible New England Holidays

Simply complete our enquiry form to get in touch, or call our Travel Specialists on 0203 924 8888


From £1,599 per person

Truly Individual Holiday Includes:

  • International flights from the UK in Economy
  • 11 nights accommodation
  • 12 days fully inclusive intermediate car hire including unlimited mileage and extra driver

Price based on two people sharing accommodation. Any element of this holiday can be tailor-made to suit you. Simply enquire below!

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  • From your first booking, you'll join My Routes Rewards - one of the most rewarding ways to travel and exclusive to us!
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