Driving in New Hampshire
Driving in New Hampshire
Cobblestone streets in Boston, Massachusetts
Cobblestone streets in Boston, Massachusetts
Salem Harbour, New Hampshire & Kennebunkport
Salem Harbour, New Hampshire & Kennebunkport
Acadia National Park & Bar Harbour
Acadia National Park & Bar Harbour
New Hampshire in the Fall
New Hampshire in the Fall
Newport & Cape Cod scenery
Newport & Cape Cod scenery

Self-Drive Best of New England

11 nights from £1,779 per person Including Flights


A picture perfect self-drive itinerary of New England. You will experience the majestic mountains of Vermont and New Hampshire, explore the beautiful coastal regions of Maine and Cape Cod and admire the glamorous mansions of Newport. This trip will be a feast for the senses with wonderful food from the farms of rural New England to the seafood of the coast and awe-inspiring sights along the way. (ATI)


  • Enjoy time in fabulous Boston, where you can walk the Freedom Trail and see the historic battleship the USS Constitution
  • Explore the stunning Acadia National Park on the north east coast
  • Admire the White Mountains of New Hampshire and the charming countryside of Vermont
  • Experience the beautiful beaches and picturesque seaside resorts of Cape Cod
  • Discover the mansions of the "Guilded Age" in Newport on beautiful Rhode Island

Itinerary Overview

Fly to Boston: 2 nights - Kennebunkport 1 night - Bar Harbor 2 nights - White Mountains 1 night - Stowe 1 night - The Berkshires 1 night - Newport 1 night - Cape Cod 2 nights - Return flight from Boston

Daily departures available between April - October

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • ATOL protection
  • In resort assistance & 24 hour contact centre
Why Book with American Sky?
  • Hassle-free - book direct quickly and easily
  • Choice of airlines and the option to switch
  • A friendly, family run business with a wealth of experience.
  • Great deals on offer for multiple destinations
  • Low deposits
Why American Sky?
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Your money is safe We safeguard your money with ATOL protection and have membership to codes of best conduct.
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Why American Sky?
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We offer expert advice and great service Our luxury tailor-made holidays are created with impeccable service from start to finish.

Day 1

Fly to Boston

Arrive at Logan International Airport. Pick up your rental car and proceed to your hotel where you will be staying for the first two nights. Enjoy your evening at leisure, exploring the city.

Day 2


The day is free to explore Boston, the cradle of American liberty. Steeped with history from the American Revolution, here you can explore any portion of the 4 mile Freedom Trail walking route which starts at Boston Common and passes 16 of the City's historic landmarks including Faneuil Hall, Paul Revere's home, the Old North Church and the USS Constitution in Boston Harbour, the oldest warship of the American navy.

Day 3

Boston – Salem – Portsmouth – Kennebunkport (90 Miles)

Along the route north of Boston lies almost four centuries of history, as well as some of the coast’s finest beaches and seascapes. First stop is Salem, the location of the infamous witch trials. Then drive along the coast to the charming harbour towns of Gloucester and Rockport. Enjoy the old-time seaport atmosphere of Portsmouth, New Hampshire and its wealth of historic buildings before crossing into Maine. Your destination today is the popular resort of Kennebunkport/Portland area, a haven for writers and artists.

Day 4

Kennebunkport – Wiscasset – Bar Harbor (210 Miles)

Today continue along Maine’s fantastically varied coastline from Brunswick to Wiscasset, which claims to be the “prettiest village in Maine.” Stop in Rockland, where several schooners offer cruises from the harbor. Then drive along a jagged peninsula to Castine and learn about the history of the 200-year struggle between four countries to possess this strategic town. Your destination today is fashionable Bar Harbor, gateway to Acadia National Park on Mt. Desert Island, and you'll be staying here for two nights.

Day 5

Bar Harbor - Acadia National Park - Bar Harbor

A full day to explore one of the oldest and most beautiful national parks in America. Discover soaring peaks, dramatic glacier-carved valleys, clear lakes, and the rugged shoreline with the only true fjord on the US Atlantic coast. Witness the area’s natural wonders from Park Loop Road or drive to the summit of Cadillac Mountain, at 1,530 feet (466 meters), the highest point on the US Atlantic seaboard.

Day 6

Bar Harbor – White Mountains/New Hampshire (230 Miles)

Your drive today takes you inland towards the spectacular scenery of the White Mountains, the “rooftop of New England,” a landscape dotted with historic villages and enchanting covered bridges. En route, experience breathtaking views of mountain ranges and pristine forests.

Day 7

White Mountains, New Hampshire – Stowe (120 Miles)

Today, traverse the White and Green Mountain ranges that divide the New England states of New Hampshire and Vermont. The route takes you through some of New England’s most beautiful scenery. Drive by Lyndonville and see Willey’s General Store in Greensboro before continuing through Craftsbury, a Grandma Moses kind of village, to Stowe.

Day 8

Stowe – Green Mountains – The Berkshires / Massachusetts (160 Miles)

Continue south along Route 100, where you will take in some of the most spectacular scenery in Vermont’s Green Mountains. With their dense forests, the mountains are home to bears, moose, wild turkey, and deer. See picture-perfect villages and some of Vermont’s famous covered bridges before crossing into Massachusetts’ Berkshires, known for their rural beauty and cultural assets. Overnight in the college town of Williamstown.

Day 9

The Berkshires – Lenox – Newport/Rhode Island (180 Miles)

Drive south and pass through a series of wonderful little towns, including Lenox, summer home for the Boston Symphony Orchestra. See Hancock Shaker Village near Pittsfield before continuing to the storied little city of Newport Rhode Island, once a prosperous colonial seaport.

Day 10

Newport – Cape Cod (100 Miles)

America’s most prominent families – from the Astors to the Vanderbilts – have summered in Newport. Some of their spectacular holiday homes are open for viewing. After sightseeing, continue along the coast on your way to Cape Cod. You'll be staying here for two nights, allowing you to explore this beautiful part of the world

Day 11

Cape Cod

A full day to explore magnificent Cape Cod with its high cliffs, rolling dunes, broad beaches, miles of walking trails, picturesque villages and delicious seafood. This peninsula is a beloved holiday spot for visitors and natives alike. Stop in Plymouth, a living panorama of Pilgrim and Colonial times and see the Mayflower II.

Day 12

Cape Cod – Boston Departure (80 Miles)

Today, leave Cape Cod and drive back to Boston. Return your car at the airport before your departure flight.

  • Return international flights
  • Fully inclusive car rental – upgrades available at a supplement (eg: SUV or convertible)
  • Hotel accommodation in 3* to 4* hotels  on a room only basis unless otherwise stated.
  • Electronic maps & driving instructions

What’s not included

  • Resort fees
  • Parking charges
  • Meals, excursions & entrance fees
  • Fuel & road tolls

Brendan White
Book today

Talk to our travel experts for more information and to book or tailor-make your holiday

01342 331798 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun

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