9 nights – Bespoke Itinerary

Days 1 to 3 – Your adventure begins in Boston.
Enjoy a day exploring this historical city. Visit the beautiful parks, walk along the Freedom Trail’, enjoy lunch at th4e artistic area of Faneuil hall and don’t forget to try the New England speciality Clam Chowder.
3 nights Boston

Day 4 – Boston to Kennebunkport.
Collect your car from downtown Boston and head north. Maybe stop by the infamous town of Salem on the way. In the afternoon relax in the pretty coastal town of Kennebunkport. (approximately 3 hours driving). 
1 night Kennebunkport.

Day 5 – Kennebunkport – Rockland
Continue north along the Main coast to Rockland. Enjoy an afternoon exploring this lovely old port town, with its historic streets and lighthouse. Don’t forget to try to famous New England Lobster. (approximately 2 hours driving). 
1 night Rockland

Day 6 – Rockland to North Conway
Head east into New Hampshire for the real start of your ‘leaf peeping’ experience. Marvel at the incredible fall colours as you head further into the mountains. Stop overnight in North Conway at the base of the White Mountains. 
1 night Conway.

Day 7 – North Conway to Stow
Driver through the mountains to Stowe, Vermont, stopping along the way to enjoy the views and colours and some of the quaint little towns en route. (approximately 2 1/2 hours drive. 
1 night Stowe. 

Day 8 – Stowe to Woodstock
Head south to Woodstock, Vermont (careful there is also a Woodstock in New Hampshire). Approximately (1 ½ hour driving). 
1 night Woodstock or nearby town.

Day 9 – Woodstock to Boston
Head back towards Boston. (approximately 2 ½ or 3 hours depending on which route your take. 
1 night Cambridge or Boston.

More time? Why not continue your fly-drive and head south to Cape Cod.

All our bespoke itineraries and can be amended to your preferences. Group tours also available.


  • Transfers
  • Accommodations
  • Car hire


  • Flights – can be added
    Travel insurance
  • Visa
  • Personal expenses and meals not stated
  • Gratuities

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