• Duration: 12 nights
  • Distance (approx): 465 miles
  • When to visit: May - Oct
  • Price: Call for info
Save this Tailor-Made Fly-Drive holiday in New England, USA
Watch the video
See the route
See the destination guide for Tailor-Made Fly-Drive Massachusetts Connecticut & Rhode Island in New England, USA
See pictures for this Tailor-Made Fly-Drive Massachusetts Connecticut & Rhode Island in New England, USA

More New England Photos

Massachusetts Connecticut & Rhode Island

A Tailor-Made Fly-Drive Holiday to New England, USA

This New England fly drive starts in Boston. Explore the City’s cultural heart. Head north via the ‘Freedom Trail’ between the picturesque and historic villages of Lexington and Concord and then west to Northfield. Discover the ‘Mohawk Trail’ where Mohawk Indians once trod this route across the rugged Berkshire Hills. Learn about the ‘Shakers’ at Hancock Shaker Village in Pittsfield. The route turns south into the state of Connecticut to New Haven – home to Yale University. Follow Long Island Sound through Mystic into Rhode Island and Bristol known as ‘the most patriotic town in America.’ Explore Newport, one of the great maritime cities of the world. Stroll along Benefit Street in Providence lined with an impressive collection of well-restored buildings that were home to merchants and sea captains. Continue to Cape Cod and explore the lovely harbour and beach town of Falmouth before heading back to Boston.



Embodies contrasts and contradictions; rich in colonial history and 21st century technology. New England’s main city and gateway with world class museums great restaurants and much more. Follow the Freedom Trail, take a harbour cruise or visit
a park (new and old).


Separated from Boston by the Charles River, home to Harvard and MIT universities as well as parks and museums.

The Litchfield Hills

The historic northwest of Connecticut has sleepy villages, hidden hiking trails and a surfeit of New England charm.


Catch up on your nautical history at America’s largest maritime museum, Mystic Seaport

New Haven

Home to Yale University with outstanding museums, theatres and art centres.

Martha’s Vineyard & Nantucket

Two picturesque islands that draw in the rich and famous with great shopping and a rich history.

Cape Cod

Sand Dunes and seashores, sunsets and windmills, colourful lighthouses and gray shingled cottages adorn the peninsula.

Mohawk Trail Scenic Byway

Forested mountains, rich river-bottom farmlands, and riotous explosions of autumn
colour have inspired travellers for generations.

To Book This Holiday or find out more call our Travel Specialists on: 01902 798008 or contact us online.

Related Brochures

Featured accommodation

Centennial House Bed and Breakfast

A rambling 17-room estate built by master craftsmen in 1811, that offers spacious guest rooms, comfortable beds, private baths and ample country breakfasts with homemade baked goods.

Additional accommodation

Inn on the Sound

Falmouth, Cape Cod, Massachusetts


1nt Boston
Lenox Hotel

92 miles to Northfield,
3 Nts
The Centennial House B&B

115 miles to New Haven,
3 Nts Swan Cove B&B

118 miles to Bristol
2 Nts Bristol Harbour Inn

63 miles to Falmouth,
2 Nts Inn on the Sound

77 miles to Boston,
1 Nt Lennox Hotel

Voted top guide book series by Wanderlust Travel Awards and endorsed by Michael Palin, we offer a visually stunning FREE DK guide book packed with information once you have confirmed your holiday.

Connected Fly/Drives

Holiday Search
Want to book more than 10 passengers?

To book your Airport Parking and Hotels and explore your other pre bookable options we recommend:
Holiday Extra Logo
Lounge Pass


Subscribe to our free email newsletter.

Your information will not be shared with any third party.

You can also join our mailing list to receive information by post.