15 Days/14 Nights – Gateway: Boston

1 & 2: Boston, MA (Old Town Trolley Tour)

Famous for everything from the Red Sox and Paul Revere to Cheers and clam “chowdah,” Boston is

a popular destination for so many reasons. Part history lesson, part modern metropolis, the Hub offers attractions to suit every taste and interest. Included is an Old Town Trolley Tour that weaves in and out of historic neighborhoods. Between landmarks, you can shop the fabulous stores on Newbury Street, have a delicious authentic Italian meal in the North End or browse the antique shops and distinctive red-brick buildings of Beacon Hill. The more culturally inclined will not want to miss the city’s world-class museums, theater and music venues. Family friendly to the core, Boston also boasts a renowned aquarium, children’s museum and science museum, making it a great getaway for all.

2 nights Boston, MA at the Taj Boston or Similar

3 & 4: Mid Coast Maine (Schooner Sailing Trip) (170 mi/272 km)

Travel to the coast, stopping in Kittery for great factory outlet shopping! Visit pretty Kennebunkport and see the oceanside summer home of former US President George Bush. Stop at historic Portland, and enjoy the charming Old Port Exchange before driving to lovely Boothbay Harbor. This colorful harbor town is a popular sailing destination and included is a delightful two hour sailing trip on a Maine schooner to see lighthouses, fishing lobstermen, wildlife and remote islands accessible only by boat.

2 nights Boothbay Harbor , ME at Greenleaf Inn

5 & 6: To White Mountains, NH (128 mi/205 km)

Journey through the Maine Lakes Region on your way to the White Mountains. Drive to North Conway,

a shoppers’ paradise with countless factory outlet stores offering top quality at rock bottom prices. Also in North Conway: the Conway Scenic Railroad; and Heritage New Hampshire museum. The Mt. Washington Toll Road takes you to the summit of one of the east’s highest mountains.

2 nights Jackson, NH at the Christmas Farm Inn or Similar

7: To Green Mountains, VT (213 mi/341 km)

Travel the Kancamagus Highway (an old Indian Trail) through some of the best scenery in the White Mountains National Forest to Lincoln. In Vermont visit Woodstock, a quintessential New England village with traditional shops and covered bridges. Your journey continues into the Green Mountains National Forest, stop in lovely Manchester Village where designer outlets frame the village green and high street.

1 night Arlington, VT at the Arlington Inn or Similar

8: To the Berkshires, MA (70 mi/112 km)

This morning cross the border into Massachusetts. Visit the Francine Clarke Art Institute or the Hancock Shaker Village, a restored 19th century settlement. Continue to Lenox, summer home of the Boston Symphony and Stockbridge, once home to Norman Rockwell, one of America’s greatest artists. The Norman Rockwell Museum houses many of his works.

1 night Bershires, MA at the Red Lion Inn or Similar

9 & 10: To Newport, RI (127 mi/203 km)

Before heading to Newport, you may visit Old Sturbridge Village, a living 19th century museum, or Mystic, Connecticut, and Mystic Seaport Museum, America’s largest maritime museum. Continue to Newport, summer resort of America’s first millionaires. Spend the day on a spectacular beach; tour the Cliff Walk and Ten Mile Drive with its extravagant summer mansions. Newport’s restored waterfront features many shops and restaurants.

2 nights Newport, RI at the Cleveland House or Similar

11 & 12: To Cape Cod, MA (Whale Watch Cruise) (95 mi/152 km)

Travel to Cape Cod, a fabulous summer resort with white sandy beaches and abundant attractions. Drive to Provincetown at the very end of Cape Cod. This colorful and fascinating little town has attracted a wide spectrum of people. Artists live side by side with traditional fisherman and during the summer Commercial Street is filled with the most cosmopolitan mix of people, exploring the art galleries, tiny seafood restaurants, shops, narrow streets and pretty gardens. Included is a whale watch cruise (weather permitting), an exciting adventure to view these majestic marine mammals, guided by an expert naturalist. Humpback whales are normally seen and you’ll never forget your first sighting of a whale blowing after a deep sea dive. Shop and stroll Main Street of historic Chatham, nearby there are sweeping views of the ocean and Chatham Lighthouse.

2 nights Cape Cod, MA at the Chatham Wayside Inn or Similar

13 & 14: Martha’s Vineyard, MA (67 mi/108 km)

Drive to Woods Hole and take the short ferry ride to the lovely island of Martha’s Vineyard (round-trip ferry tickets for you and your car are included). Two days to relax on the island, a Mecca for summer visitors, that has played host to the rich and famous, including film stars and American Presidents. Tour the Vineyard to see the gingerbread cottages of Oak Bluffs and Gay Head cliffs in scenic Aquinnah.

2 nights Martha’s Vineyard, MA at the Harbor View Hotel or Similar

15: To Boston (90 mi/144 km)

A last leisurely morning on the island and then drive to the ferry and on to Logan Airport, and your flight home.

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