New England Explorer

  • Connecticut + 4 more
  • Self Drive Ideas
  • 8 Days
from  £659pp
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New England is interesting and fascinating. Enjoy the mountain and lake scenery, the wonderful hiking and biking trails, the crisp air and delicious food.

A Free Personalised Road Book is included as standard with our Self Drive itineraries. 


Please note: – This is a suggested itinerary only and is intended to give an overview of what is possible. All of our holiday itineraries are fully customisable and can be tailor-made to suit your own individual requirements.  If you would like to start in a different destination, use specific hotel accommodation, include an extra night here, a side-trip there and/or include tickets to an event please let your Discover North America travel specialist know. They’ll also book you the best value flights to ensure a seamless holiday experience.


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Day 1 Boston

Arrive at Logan International Airport. Pick up your rental car and proceed to your hotel. Enjoy your evening at leisure.

Day 2 Boston

A full day free to explore Boston, the cradle of American liberty. The Revolutionary era comes to life along the Freedom Trail walking route. Visit the haunts of the patriots who stoked the fires of democracy throughout the Colonies.

Day 3 Boston – Coastal Maine (115mi/185km)

Along the route north of Boston lies almost four centuries of history, as well as some of the coast’s fi nest 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. Pass through Kennebunkport, summer home to Presidents, and enjoy exploring Portland, Maine’s largest city.

Day 4 Coastal Maine – White Mountains (115mi/185km)

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 5 White Mountains – Stowe (130mi/210km)

Today, traverse the White Mountains that divide the New England states of New Hampshire and Vermont. The mountains are home to bears, moose, wild turkey, and deer. This 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. See picture-perfect villages and some of Vermont’s famous covered bridges.

Day 6 Stowe – Green Mountains – Connecticut River Valley (180mi/285km)

Your drive today takes you alongside the Green Mountains of Vermont, part of the Appalachian Mountain range that stretches from Quebec in the north to Alabama in the south, and through the Connecticut River Valley. Step into Old Sturbridge Village and find yourself transported back in time. In historic households and shops, at water-powered mills and on working farms, explore the everyday tasks and seasonal celebrations of early 19th-century New England.

Day 7 Connecticut Valley River – Cape Cod (188mi/300km)

Journey south towards the Massachusetts coast. Many of America’s most prominent families – from the Astors to the Vanderbilts – have summered in Newport. Many of their homes are now preserved and open for tours. Continue along the coast on your way to the Cape. 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 vacation spot for visitors and natives alike. Stop in Plymouth, a living panorama of Pilgrim and Colonial times and see the Mayflower II.

Day 8 Cape Cod – Boston (75mi/120km)

This morning drive back to Boston and return your car in time for your departure flight.