Classic New England Self-Drive

14 nights from £3,695 per person

Best time to travel APR - OCT

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Itinerary Highlights

  • Board Lulu, a traditional lobster boat for a two-hour tour of Bar Harbor for a lobster fishing and seal watching experience
  • Take a scenic train ride to the summit of Mount Washington on the world's first mountain-climbing cog railway
  • Take a tour through Ben and Jerry's Ice Cream Factory in Waterberry, indulge in your favourite flavours and take a walk through the Flavor Graveyard to pay your respects to the flavours of past years
  • Wander through the grounds and rooms of Newport Mansions, former summer homes of the Astors and Vanderbilts

What's Included

  • Inspiring Travel Company - Accommodation Throughout Accommodation Throughout
  • Inspiring Travel Company - Car Hire Car Hire
  • Inspiring Travel Company - GPS Device GPS Device
  • Inspiring Travel Company - International Flights International Flights
14 nights from £3,695 per person
Best time to travel APR - OCT
All of our holidays are tailor-made to your requirements by an expert Travel Specialist
Enquire Now Video Consultation

Discover the rich history of the American Revolution on Boston's Freedom Trail. Feast on fresh Lobster and seafood in Maine. Scenic drives take you through the White Mountains and rural villages of the Berkshires. Visit the famous mansions of Newport and watch for whales at Cape Cod.

Classic New England is an all-encompassing suggested fly-drive holiday taking you to five of the states of New England. Starting and ending in Boston, enjoy the best of this area's coastline, beaches, mountain villages and cities. This itinerary ensures culture, history and scenic beauty are discovered in the five states.

Take the Freedom Trail walking tour in Boston for an insight in to the history of the American Revolution. Board Lu Lu's lobster boat in Bar Harbor, Maine for a lobster fishing and seal watching experience and explore the stunning Acadia National Park. Take the scenic drive through forests and pass lakes and rivers on the way to the White Mountains of New Hampshire where you take the world's first mountain-climbing cog railway to the summit of Mount Washington for scenic views of New Hampshire and on a clear day as far as Canada.

Next, indulge in Ben & Jerry's at their Ice Cream factory in Waterberry, Vermont before going back in time with a self-guided tour through the Hancock Shaker Village in Pittsfield, Massachusetts. Head to the yachting town of Newport on Rhode Island, where the Preservation Society has restored and protected many of the grand and gracious Newport Mansions which are now open to the public to enjoy. Your last stop is Cape Cod, where you can spend lazy days on the pristine beaches, visit the lighthouses and take a boat tour out on the ocean in search of migrating whales and other marine life.


Day 1  Boston
Begin your fly-drive holiday with a stay in Boston, a city with plenty of old world charm and history.
Day 2  Boston

Start your day with a walking tour along the Boston Freedom Trail, led by a knowledgeable 18th century costumed guide. The rest of the day is free for you to explore more of Boston such as the antique shops of Beacon Hill, the shops of Newbury Street and the fashionable area of Back Bay. Perhaps go on a trolley or duck tour of the city and visit some of the great museums, many of which are also great for families.

Day 3  Boston to Kennebunkport, Maine (90 miles)
Kennebunkport, Maine
Collect your rental vehicle from the Boston downtown depot and drive north to Maine, stop off in Kittery to go outlet shopping. Enjoy free time to explore the quaint coastal town of Kennebunkport with its gorgeous long sandy beaches, Seashore Trolley Museum and highly rated restaurants on Dock Square.
Day 4  Kennebunkport to Bar Harbor, Maine (203 miles)
Bar Harbor, Maine
Continue your drive north following the coast to Bar Harbor, the gateway to the mountains and cliffs Acadia National Park. Go hiking to the Cadillac Mountain and spend time following the village trails along the picturesque shore.
Day 5  Bar Harbor, Maine
Bar Harbor, Maine
Start your day with a two-hour Lulu Lobster Boat Ride where you will learn more about the local lobster fishing industry and watch seals basking on the rocks at low tide or swimming and playing in the surf at high tide. Board the Lulu Lobster Boat Tour and sail around the harbour gaining an insight in to the Lobster fishing industry and looking out for marine life.
Day 6  Bar Harbor, Maine to Mt Washington, New Hampshire (250 miles)
Mt Washington, New Hampshire
Travelling from Bar Harbor to Mt Washington, you’ll pass forests, fields, lakes, rivers and beautiful scenery.
Day 7  White Mountains, New Hampshire
Mt Washington, New Hampshire
Once in the White Mountains, take the world's first mountain-climbing cog railway to the summit of Mount Washington where you will be rewarded with panoramic views of New Hampshire and as far as Quebec, Canada.
Day 8  White Mountains, New Hampshire to Woodstock, Vermont (130 miles)
If you spent the previous nights in Jackson or North Conway, you can travel on the Kancamagus Highway, a scenic journey, to Lincoln. Arriving in Vermont, visit the Ben & Jerry’s Ice Cream Factory, see Lake Champlain from Burlington.
Day 9  Woodstock, Vermont
Visit a typical New England village (Stowe) and also if you wish, the Shelburne Museum with its side-wheeler, gardens and Americana feel.
Day 10  Woodstock, Vermont to Stockbridge, Massachusetts (174 miles)
Today you’ll travel to Rutland, once the centre of the Vermont marble industry and en route to The Berkshires, stop off at Manchester Village. You may also wish to visit the Francine Clark Art Institute or the Hancocker Shaker Village. In Lenox, you can enjoy a performance by the Boston Symphony (depending on the season) and in Stockbridge, the very interesting museum in honour of Norman Rockwell, the American illustrator. Accommodation: Red Lion Inn
Upgrade accommodation to  Wheatleigh
Day 11  Stockbridge, Massachusetts to Newport, Rhode Island (127 miles)
Before arriving at your next destination, visit the Old Sturbridge Village, a living 19th-century museum or the Mystic Seaport Museum in Mystic, Connecticut. Travel onwards to Newport where you’ll spend time in this charming yacht town.
Day 12  Newport, Rhode Island
The summer resort of America’s millionaires of the past, Newport is home to some beautiful summer mansions as well as stylish shops and restaurants (included in your holiday is admission to three mansions).
Day 13  Newport, Rhode Island to Cape Cod, Massachusetts (75 miles)
Your final destination of Cape Cod is a real treat; a time to relax on the white beaches, go on a whale watching cruise (from Hyannis and included in your holiday).
Day 14  Cape Cod, Massachusetts
Visit the pretty town of Chatham and alternative Provincetown also known as P-Town. You can also take ferries to the islands of Martha’s Vineyard and Nantucket if you wish.
Staying at  Chatham Bars Inn
Day 15  Boston (75 miles)
In the morning, drive to the Plimoth Plantation to learn about 16th century life in this living museum and then travel onwards to Boston for your flight home or extend your holiday further in Boston.
Classic New England Self-Drive
14 nights from £3,695 per person
All of our holidays are tailor-made to your requirements by an expert Travel Specialist
Enquire Now
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