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
  • Best time to travel May - October

What's Included

  • Accommodation Throughout
  • Car Hire
  • GPS Device
  • International Flights
14 nights from £5,499 per person


Travel Specialist

I'm here to tailor-make your perfect North America holiday. Give me a call and I'll use my expertise to create your personalised experience.

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 heading 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.


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

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.

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.
Bar Harbor, Maine
Continue your drive north following the coast to Bar Harbor, the gateway to the mountains of Acadia National Park. There are several attractions along the way such as Portland with its attractive waterfront of converted warehouses and working fishng wharves. Rockport and Camden are quaint seaside towns with attractive "Main Streets" and a selection of interesting boutiques and eateries, making this an ideal lunch stop before reaching Bar Harbor.
Bar Harbor, Maine
Take a full day to explore the 47,000-acre Acadia National Park. The park is an outdoor playground with miles of hiking and biking trails, wildlife viewing and fishing. You can join a guided tour or explore the park at your leisure by car or bike. Attractions include Cadillac Mountain where spectacular panoramic views will take your breath away. Take in the dramatic views andthe ocean waves creating a thunderous sound at Thunder Hole.
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.
Mt Washington, New Hampshire
Travelling from Bar Harbor to Mt Washington, you’ll pass forests, fields, lakes, rivers and beautiful scenery.
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.
Woodstock, Vermont
Depart Mount Washington and cross the border in to Vermont. For those that love ice cream, take a short diversion to Waterbury Village Historic District with its historically and architecturally distinctive structures. Waterbury is also the home of Ben & Jerry's Ice cream Factory where youenjoy a tour and even enjoy a private VIP experience of making ice cream with one of the flavour gurus.
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.
There are several routes from Woodstock to Newport you can take today. A scenic route along the border of Vermont and New Hampshire and on through the city of Worcester, Massachusetts or cut across country via New Hampshire's capital city, Concord and through Boston.
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. Several of Newport's Mansions are open to the public, such as The Breakers and Marble House, and can be visited on guided tours.
Your final destination of Cape Cod is a real treat; a time to relax on the white beaches, go on a whale watching cruise, or take a ferry across to discover the quaint and quintessential New England island of Nantucket.
Visit the pretty town of Chatham and alternative Provincetown also known as P-Town. You can also take ferries to the island of Martha’s Vineyard.
Staying at   Chatham Bars Inn
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.


Travel Specialist

Not sure where to stay in North America? I'm here to help. Give me a call and I'll share my first-hand insights to find your perfect spot.

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14 nights from £5,499 per person

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