• Duration: 14 nights
  • Price: Call for info
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Classic New England

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

Price Guide accommodation only:

Based on twin/double Standard grade from  £585 pp  

Select grade from £905 pp


Coast and mountains, nature and culture, shopping and sightseeing, excitement and relaxation – this Classic holiday has them all. Explore the pedestrian friendly city of Boston on foot and visit the shops, museums and famous landmarks. The Maine coast is rugged and beautiful with pretty villages and larger towns such as Kennebunkport and Portland, along the way take the opportunity to sample the famous Maine lobster – delicious! 

Continue from the coast to the mountains of New Hampshire and Vermont through countryside dotted with lakes and rivers to the Connecticut River Valley and south to Newport, Rhode Island and finally the summer playground of the rich and famous – Cape Cod.

New England Fly drive





New Hampshire                    

White Mountains and scenery



Green Mountains and Ben and Jerry’s ice cream factory



Boston , Hancock Shaker Village, Cape Cod and Martha’s Vineyard

Rhode Island                       

10 Mile Drive mansions in Newport

To Book This Holiday or find out more call our Travel Specialists on: 01902 798008 or contact us online.
Tailor-Made Fly-Drive Classic New England in New England, USA
Tailor-Made Fly-Drive Classic New England in New England, USA

Featured accommodation

Hotel Viking

A luxurious historic hotel conveniently located close to many of Newport’s attractions. The hotel features fine dining and beautifully designed guestrooms.

Additional accommodation

Eagle Mountain House

Jackson, New Hampshire


1 & 2: Boston, MA

Famous for everything from the Red Sox and Paul Revere to Cheers and clam “chowdah,” Boston is a popular destination for so many reasons. Part history lesson, part modern metropolis, the Hub offers attractions to suit every taste and interest. 

Hop on the Freedom Trail, a well-preserved pedestrian path that weaves in and out of historic neighborhoods. Between land-marks, you can shop the fabulous stores on Newbury Street, have a delicious authentic Italian meal in the North End or browse the antique shops and distinctive red-brick buildings of Beacon Hill. 

The more culturally inclined will not want to miss the city’s world-class museums, theater and music venues. Family friendly to the core, Boston also boasts a renowned aquarium, children’s museum and science museum, making it a great getaway for all.


2 nights Boston, MA

3: To Mid Coast Maine (112 mi/180 km)


Travel to the coast, stopping in Kittery for great factory outlet shopping! In historic Portland, enjoy the charming Old Port Exchange and, of course, lobster!


1 night Mid Coast Maine

4 & 5: To Bar Harbor, ME (162 mi/259 km)


Spectacular scenery awaits, as you head for Bar Harbor situated on Mount Desert Island, known as the home of Acadia National Park with its lakes, forest, coast-line and more than 300 species of birds. 

Either hike or drive to the top of Cadillac Mountain -- the highest point on the eastern seaboard -- and you’ll be the first in the country to welcome the sun. Above you the early morning sky; below, Maine’s rugged coastline. 

When your trek ends, head over to Bar Harbor, the island’s hub, where you’ll find more than 100 restaurants.  Explore its sidewalk cafes and shops, or wander the waterfront and gaze at the 19th-century mansions that tower over the water, stately reminders of the days when this small town on Frenchman’s Bay was a grand summer resort for society families.

2 nights Bar Harbor, ME

6 & 7: To White Mountains, NH (250 mi/403 km)


Drive through gorgeous scenery – from forests to fields, all interspersed with sparkling lakes and rivers to the White Mountains.

 In the White Mountains, drive to the summit of Mt. Washington, shop, or take the Conway Scenic Railroad, or head to the Lakes Region.


2 nights White Mountains, NH

8 & 9: To Northern Vermont, VT (130 mi/208 km)

If you spent the night in Jackson or North Conway, travel the Kancamagus Highway to Lincoln. In Vermont, treat yourself to a tour of Ben & Jerry’s Ice Cream Factory before heading to Burlington, on the banks of Lake Champlain.

Head for Woodstock, a quintessential New England village with traditional shops and covered bridges. Visit Shelburne Museum’s collections of Americana, gardens and the side- wheeler, SS Ticonderoga.


2 nights Northern Vermont, VT

10: To Connecticut River Valley, MA (174 mi/278 km)


Travel to Rutland, once center of the Vermont marble industry. Manchester Village is a lovely stop on your way to the Berkshire Hills of Massachusetts. Visit the Francine Clarke Art Institute or the Hancock Shaker Village, a restored 19th century settlement. 

Continue to Lenox, summer home of the Boston Symphony and Stockbridge, once home to Norman Rockwell, one of America’s greatest artists. The Norman Rockwell Museum houses many of his works.


1 Night Connecticut River Valley, MA

11 & 12: To Newport, RI (127 mi/203 km)


Before heading to Newport, you may visit Old Sturbridge Village, a living 19th century museum, or Mystic, Connecticut, and Mystic Seaport Museum, America’s largest maritime museum. 

Continue to Newport, summer resort of America’s first millionaires. Spend the day on a spectacular beach; tour the Cliff Walk and Ten Mile Drive with its extravagant summer mansions. Newport’s restored waterfront features many shops and restaurants.


2 nights Newport, RI

13 & 14: To Cape Cod, MA (75 mi/120 km)


Travel to Cape Cod, a fabulous summer resort with white sandy beaches and abundant attractions. Plan a whale watch cruise; visit historic Chatham or colorful, artistic Provincetown. Take a day trip to Martha’s Vineyard or Nantucket.2 nights Cape Cod, MA

15: To Boston, MA (75 miles/120 km)


Boston’s Logan Airport is approximately 1.5 hours drive from Cape Cod and en-route you’ll have time to visit picturesque Sandwich, the Cape’s oldest town and at Plymouth the Plimoth Plantation, a living museum of 1627 life.


Time for lunch before driving to the airport.

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.

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