This itinerary shows you most of New England’s main highlights. Stop off in the Berkshires, a popular holiday haunt for Boston’s and New York’s elite since the 1800s; discover glorious mountains in New Hampshire and green scenery in Vermont; and savour stunning sea views in Newport, Rhode Island.
Suggested route & duration
Suggested duration: 14 nights
• Boston, Massachusetts: 2 nights
• Kennebunkport, Maine: 1 night
• Bar Harbor, Maine: 2 nights
• Jackson, New Hampshire: 2 nights
• Vergennes, Vermont: 2 nights
• Stockbridge, Massachusetts: 1 night
• Newport, Rhode Island: 2 nights
• Falmouth: 2 nights
About this independent tour
Why you’ll love this self-drive
• Hop on the ferry to beautiful Martha’s Vineyard from Falmouth or hit Cape Cod’s beaches
• Follow the Ocean Drive or the Cliff Walk and visit the breathtaking mansions in Newport
• Relax by the waterfront in Bar Harbor on Maine’s Mount Desert Island, a gateway to the awe-inspiring Acadia National Park
• This itinerary can also be done in a motorhome.
Suggested self-drive details
Day 1: Boston Enjoy a couple of nights in this attractive and historic New England city. Stay 2 nights at DoubleTree by Hilton Boston - Downtown.
Day 3: Kennebunkport Unwind on lovely white-sand beaches in this coastal town in Maine. Stay at The Nonantum Resort.
Day 3: Bar Harbor Soak up views over Frenchman’s Bay from this picturesque coastal town on Mount Desert Island in Maine. Stay 2 nights at Bluenose Inn - a Bar Harbor Hotel.
Day 6: Jackson Admire the green landscapes in this small town tucked in New Hampshire’s White Mountains. Stay 2 nights at Christmas Farm Inn & Spa.
Day 8: Vergennes Visit the pretty Vergennes Fall Park during your two-night stay in Vermont. Stay 2 nights at Basin Harbor Club.
Day 10: Stockbridge This small town in the Berkshires has historic homes and a charming main street. Stay at The Red Lion Inn.
Day 11: Newport Lap up chic seaside vibes at the yacht-filled harbour in one of Rhode Island’s most well-known cities. Stay 2 nights at Newport Beach Hotel & Suites.
Day 11: Falmouth Browse friendly local cafés and head to Cape Cod’s superb beaches. Stay 2 nights at Inn on the Square.
Ben & Jerry’s
Take a tour of the much-loved ice cream brand’s factory near Stowe in Vermont
Vermont Route 100
Drive this scenic highway which stretches nearly the entire length of the state
Visit Massachusetts Museum of Contemporary Art (MASS MoCA), a creatively converted factory
‘Gilded Age’ Mansions
Visit The Breakers in Newport, an Italian Renaissance-style property built by the Vanderbilts
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
Good-value chain hotels are easy to find but we’ve selected some wonderful boutique places which give you a taste of New England. We love The Red Lion Inn at the heart of Stockbridge – it’s right on the main street and its elegant dining room serves food from local farms.
New England is full of fantastic things to do, with some especially cool spots in Newport. Taste the incredible seafood with a delicious hot lobster roll at the Lobster Bar, or cruise around the historic harbour on the Rum Runner II, built during the height of Prohibition in 1929.
This is a long itinerary but there’s plenty more to see. Spend an extra night in Boston to see the Red Sox’s Fenway Park; hike some of the Appalachian Trail in the Berkshires; or see the cobblestone streets and cute beach cottages of Nantucket with a day trip from Falmouth.
For great food head to Portland, Maine – it has been named the USA’s top foodie city. We also love Connecticut – there’s Yale University in New Haven or the captivating seaport town of Mystic, where The Mayflower II replica is being restored for the 400th anniversary of The Mayflower sailing.
Good to know
When to go
• Visit during autumn to see the beautiful fall foliage throughout New England
• Whales can be spotted off the coast from May to October – cruises depart from towns like Kennebunkport, Boston and Bar Harbor
• We recommend travelling to Cape Cod from April to June or early September, to escape the crowds during the busier summer and leaf-peeping months