New England: Boston, Maine and Connecticut | Out Of Office | Tailor-made luxury holidays inclusive of all
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Boston, Maine and Connecticut

New England: Boston, Maine and Connecticut

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New England is best known for its Colonial past, forested mountains and dramatic Atlantic coastline. Explore the history of Boston on the Freedom Trail which passes through critical historical sites in one of the oldest cities in the US. Having your own set of wheels means you can explore at your own pace and take in many of the stunning mountain ranges from the comfort of your seat.

time difference


5-8 hours behind the UK

flight time


7-11 hours direct from UK

Day 1


Collect the keys to your new set of wheels and your explorations can begin. 

Day 2


A full free day in Boston is the perfect opportunity to work out the lay of the land. Bring the Revolutionary era to life through the Freedom Trail walking route, an absolute must. Immerse yourself in history as you visit the haunts of patriots who stoked the fires of democracy throughout the Colonies.

Day 3

Boston - Coastal Maine

North of Boston you’ll find over four hundred years history, in addition to some of the coast’s finest beaches and seascapes. Your first stop is Salem which was the location of infamous witch trials. Second, the charming harbour towns of Gloucester and Rockport. Soak up the old-time seaport atmosphere of Portsmouth, New Hampshire and stroll around the variety of historic buildings. Next, you’ll cross into Maine and pass through Kennebunkport, summer home to Presidents. Spend your evening discovering Maine’s largest city, Portland.

Day 4

Coastal Maine - White Mountains

Today you’ll drive inland towards the White Mountains, the rooftop of New England. Stop off en route to take in the breathtaking views of mountain ranges and pristine forests. Experience spectacular scenery dotted with historic villages and enchanting covered bridges.

Day 5

White Mountains - Stowe

Today you will travel between the New England states of New Hampshire and Vermont along the White Mountains, home to bears, moose, wild turkey and deer.  Drive by Lyndonville and see Willey’s General Store in Greensboro before continuing through Craftsbury, a Grandma Moses kind of village, to Stowe. See some of Vermont’s famous covered bridges and picture-perfect villages.

Day 6

Stowe - Green Mountains - Connecticut River Valley

Today you’ll drive alongside the Green Mountains of Vermont. Part of the Appalachian Mountain range, the Green Mountains cut through the Connecticut River Valley, stretching from Quebec in the north all the way to Alabama in the south. Find yourself transported back in time as you step into Old Sturbridge Village. Learn about life of early 19th-century New England during your visits to historic households and shops, water-powered mills and working farms.

Day 7

Connecticut River Valley - Cape Cod

On your penultimate day, make your way south towards the Massachusetts coast. Many of America’s most prominent families have summered in Newport - from the Astors to the Vanderbilts. Several of their homes have been preserved and are open for tours. The peninsula in Cape Cod is popular with both natives and tourists as a great vacation spot, as well as the high cliffs, rolling dunes, broad beaches, miles of walking trails, picturesque villages and delicious seafood. Stop in Plymouth, a living panorama of Pilgrim and Colonial times and see the Mayflower II.

Day 8

As your explorations draw to a close, make your way to Boston airport.

Travel Info

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