This is where old world charm, tales of the past and dramatic coastal backdrops meet. This 12-night self-drive ticks off New England’s not-to-be-missed highlights: Boston’s heritage, New Hampshire’s mountains, Maine’s ruggedly beautiful shoreline and Cape Cod’s blissful beaches and sun-bleached nautical style.
Suggested route & duration
12 nights from Boston
• Boston: 2 nights
• Jackson: 2 nights
• Portland: 1 night
• Bar Harbor: 2 nights
• Kennebunkport: 1 night
• Gloucester: 1 night
• Falmouth: 3 nights
About this independent tour
Why you’ll love this self-drive
• Follow the heritage-rich Freedom Trail, a 2½-mile walking route that takes in Boston’s numerous historic sites
• Stay in New England inns that are bursting with character
• Take the cog railway up to the peak of Mount Washington
• Soak in Acadia National Park’s awesome coastal views from sea level or the park’s mountain trails
• Visit Cape Cod’s beautiful beaches, iconic lighthouses and full-of-charm towns
• This itinerary can also be done in a motorhome.
Suggested self-drive details
Day 1 Boston Begin your holiday in Boston, a city full of Revolutionary heritage. Stay 2 nights at DoubleTree by Hilton Downtown.
Day 3 Jackson Head inland towards New Hampshire’s White Mountains, home to the North East’s highest mountain. Stay 2 nights at Christmas Farm Inn & Spa.
Day 5 Portland Cross into Maine and return to the coast for a night in up-and-coming Portland. Treat yourself to dinner at one of the waterfront seafood joints. Stay at Hyatt Place Portland Old Port.
Day 6 Bar Harbor Spend two nights on Mount Desert Island and explore Acadia National Park. Stay 2 nights at The Bluenose, a Bar Harbor Hotel.
Day 8 Kennebunkport Begin your journey back south, visiting a few of New England’s famous light houses on your way to Kennebunkport. Stay at The Nonantum Resort.
Day 9 Gloucester Step back in time in Gloucester, one of the region’s oldest cities and the inspiration for Rudyard Kipling’s book, Captain Courageous. Stay at Ocean House.
Day 10 Falmouth On your way to Cape Cod, visit Salem which is known for its 17th-Century witch trials, and Plymouth: the site of the first Pilgrim settlement. Spend the next couple of days exploring the Cape’s beaches and enchanting coastal towns. Stay 3 nights at the Inn on the Square.
The Freedom Trail
The best way to see Boston’s historic highlights is by following the red-bricked Freedom Trail
Take the steeply ascending cog railway to the peak of Mount Washington for far-reaching vistas
Acadia National Park
Explore miles of coastline, woodlands and lakes and scale magnificent granite mountains
Cape Cod is the sun-kissed vacation destination of choice for east coast city dwellers
Tailor your tour
Make it your own
We’ve crafted this self-drive based on our own experiences and customers’ feedback. It’s fully flexible, so talk to us and we can create your perfect trip.
Where to stay
The hotels featured on this self- drive really give you a sense of place. They are mostly boutique inns that are independently run; and while not ultra-luxurious, they have oodles of New England appeal. There are a handful of high-end hotels you can upgrade to such as the Chatham Bars Inn on Cape Cod and the Taj Boston.
There are plenty of amazing things you can do on this round trip from Boston. A few of our favourites include taking the cog railway to the peak of Mount Washington, driving Acadia’s Park Loop scenic road and heading over the water to the upmarket vacation spots of Martha’s Vineyard and Nantucket from Falmouth.
We suggest spending at least two nights in most of the places you visit on this road trip. We’ve included three nights in Falmouth to give you time to explore Cape Cod and the nearby islands but there’ll definitely be enough to do if you want to extend your time here. Another night or two in Bar Harbour is also recommended, especially if you like hiking.
There are so many other destinations you can add to this itinerary. These include the towns and cities of Connecticut and Rhode Island, Massachusetts’s beautiful Berkshires and even the iconic eastern USA cities of New York, Washington D.C. and Philadelphia.