DAY 1

Boston

Visitors can familiarize themselves with the some of the city’s neighborhoods, including architecturally significant Back Bay, bustling downtown with Faneuil Hall Marketplace, the North End with its historical sites, Italian restaurants and late-night cafes, and the new, vibrant Seaport District, alive with restaurants, night clubs, and local breweries – just to name a few.

DAY 2

Boston and Cambridge

Explore Boston’s highlights including the Freedom Trail, a 1.6-mile trail to the important historical sites from colonial and revolutionary times, the Back Bay where one can find architectural highlights such as Trinity Church, voted the most beautiful church building in the United States by the American Institute of Architects, and the Fenway which boasts the Museum of Fine Arts and the Isabella Stewart Gardner Museum. Along the waterfront one can join a harbor cruise or whale watch, or cross the Charles River to Cambridge and visit Harvard University.

DAY 3

Boston – Portsmouth – Kennebunkport, ME (84mi/134km)

Travel north, making a stop in Portsmouth, New Hampshire, a working port since colonial days and a treasure trove of historical offerings. Continue to Kennebunkport which boasts numerous, large seaside estates along Ocean Avenue, the one-of-a-kind Wedding Cake House and quaint shops at Dock Square.

DAY 4

Kennebunkport – Ogunquit – Kennebunkport (22mi/18km)

Take a short drive to Ogunquit, Maine. This beach community boasts a long, white sand beach, fine shops and galleries, and the Marginal Way, a magnificent mile-long footpath that follows the edge of the Atlantic atop rugged cliffs. Browse the galleries and enjoy fresh lobster rolls at Perkins Cove.

DAY 5

Kennebunkport – Portland – Whitefield, NH (154mi/246km)

Explore Portland’s historic buildings, Old Port Exchange and take a cruise to see famous light houses. Travel through Maine’s picturesque lakes region and into New Hampshire. Travel along the scenic Kancamagus Highway, well known as one of the best Fall Foliage viewing areas in the country and designated an American Scenic Byway.

DAY 6

Whitefield – Lincoln – Whitefield (50mi/80km)

Venture through Franconia Notch and see natural wonders such as Indian Head, hike into Flume Gorge, or take a tram to the summit of Cannon Mountain for breathtaking views.

DAY 7

Whitefield – Stowe, VT (80mi/128km)

Scenic routes and covered bridges wind into Vermont, the Green Mountain state. Experiences like Morse Farm to see how Maple Syrup is made and a tour at Ben & Jerry’s Ice Cream Factory can be done en route to the charming village of Stowe, at the base of Mt. Mansfield.

DAY 8

Stowe – Burlington – Stowe (72/115km)

From Stowe it’s an easy drive into Burlington, Vermont’s largest city, on the shores of Lake Champlain. One can take a cruise along the lake, stroll Church Street Marketplace or visit the Shelburne Museum just south of Burlington. The Shelburne Museum is one of the nation’s finest, most diverse and unconventional museums of art and Americana. Exhibits are situated in 39 buildings spread over magnificent grounds.

DAY 9

Stowe – Manchester – Williamstown, MA (158mi/253km)

Head south to Manchester, known as both Manchester Village and Manchester Center. One is known for its mansions, art center and Hildene, the former estate of Robert Todd Lincoln, Abraham Lincoln’s son and now a museum. The other is known for its renowned outlet stores. Picturesque Route 7 takes travelers into the Berkshires of Massachusetts.

DAY 10

Williamstown – Berkshires –Williamstown (44mi/70km)

Williamstown is home to Williams College and the summertime’s renowned Williamstown Theater Festival. Neighboring North Adams boasts the Massachusetts Museum of Contemporary Art. Tanglewood, the Boston Symphony’s summer home is in Lenox. Stockbridge is home to the Norman Rockwell Museum, famous for his Saturday Evening Post covers. In Hancock, Hancock Shaker Village, a beautifully restored village, set on 1,200 acres of farm, woodland and pasture, is home to a premier collection of Shaker buildings and artifacts.

DAY 11

Williamstown – Mystic, CT (155mi/248km)

Wind through country roads to Connecticut’s Northwest corner, better known as “antique country” with its quaint antique stores, museums and gardens. Continuing to the coast, Mystic, Connecticut is known for Mystic Seaport, the Museum of America and the Sea. Set on 17 acres, it depicts 19th c. seafaring life.

DAY 12

Mystic – Newport, RI (50mi/80km)

Traveling north into Rhode Island, Newport is where one will find the opulent summer homes of the Vanderbilts and the Astors, the church where John F. Kennedy married Jacqueline Bouvier, the waters where the Americas Cup Race sailing race has been held, Touro Synagogue, the first in the United States, and the Old Stone Mill, believed to be built by the Vikings around 1100AD.

DAY 13

Newport (10mi/16km)

Traveling along Ocean Drive and Millionaire’s row allows visitors to see the magnificent mansions of the Gilded Age and are open to the public under the stewardship of the Newport Preservation Society. Other sites of interest include the International Tennis Hall of Fame and the historic Brick Marketplace.

DAY 14

Newport – Falmouth, MA (69mi/110km)

Continue into Plymouth, “America’s hometown”. There one can see Plymouth Rock, tour the Mayflower II, an exact replica of the ship that carried the Pilgrims to the New World Village and Wampanoag site. Cross the Cape Cod Canal to a world of charm and beauty to spend the next 2 nights on Cape Cod.

DAY 15

Falmouth – Provincetown – Falmouth (160mi/256km)

A drive along the Cape Cod National Seashore allows one to explore lighthouses, quaint coastal communities, and natural scenic beauty. Visit the lively artist colony of Provincetown and take a whale watch. Boutiques and fine dining restaurants align Chatham’s Main Street.

DAY 16

Falmouth – Boston (75mi/120km)

Morning to relax on the Cape or enjoy more sightseeing in the village of Sandwich. Its Heritage Museum and Gardens and Sandwich Glass Museum are both worth a visit. Return to Boston for departure.