Classic New England Fly-Drive

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 Fly-Drive

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.

Boston, USA
    DAY 01



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

    Back Bay, Boston
      DAY 02



      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.

      Accommodation Options

      kennebunkport,  maine
        DAY 03

        Mid-Coast Maine (90 miles)

        Maine Coast (Maine)

        Collect your rental vehicle from the Boston downtown depot and drive north to Maine, stop off in Kittery to go outlet shopping or in Portland to see the Old Port Exchange and enjoy a lunch of lobster or other local seafood specialties. 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.
        acadia national park maine
          DAY 04

          Bar Harbor, Maine (190 miles)

          Maine Coast (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.
          bar harbor maine
            DAY 05

            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.
            White Mountains, New Hampshire
              DAY 06

              White Mountains, New Hampshire (250 miles)

              White Mountains (New Hampshire)

              Travelling from Bar Harbor to the White Mountains, you’ll pass forests, fields, lakes, rivers and beautiful scenery. Accommodation Options

              white mountains new hampshire
                DAY 07

                White Mountains, New Hampshire

                White Mountains (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. Accommodation Options

                kancamagus highway usa
                  DAY 08

                  Woodstock, Vermont (130 miles)

                  Stowe & Woodstock (Vermont)

                  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. Accommodation Options

                    DAY 09

                    Woodstock, Vermont

                    Stowe & 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. Accommodation Options

                      DAY 10

                      Stockbridge, Massachusetts (174 miles)

                      Lenox & The Berkshires (Massachusetts)

                      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 Options

                        DAY 11

                        Newport, Rhode Island (127 miles)

                        Newport & Providence (Rhode Island)

                        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. Accommodation Options

                          DAY 12

                          Newport, Rhode Island

                          Newport & Providence (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). Accommodation Options

                            DAY 13

                            Cape Cod, Massachusetts (75 miles)

                            Cape Cod & The Islands (Massachusetts)

                            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). Accommodation Options

                              DAY 14

                              Cape Cod, Massachusetts

                              Cape Cod & The Islands (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. Accommodation Options

                              plimoth plantation
                                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.
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