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Inn side New England
DAY 1 Boston/The Fairmont Copley Plaza
Arrive Boston. Transfer to your hotel in downtown Boston for the overnight. This evening, explore Boston’s many restaurants, enjoy a show in Boston’s theater district or stroll through lively Quincy Marketplace.

DAY 2 Boston – Ogunquit – Scarborough/Black Point Inn (114mi/183km)
Pick up your rental car and depart for the Maine coast. Stop in Ogunquit. This quaint fishing hamlet is one of the most picturesque and enjoyed seaside resort villages in New England. Walk the mile-long Marginal Way over rocky ocean cliffs to Perkins Cove. Enjoy a mouth-watering lobster luncheon before continuing along the scenic coastal route through Kennebunkport dubbed “a magical place by the sea” into Scarborough. Located on a little peninsula and surrounded by water on three sides,this hotel boasts a stone fireplace and relaxed New England feel. Enjoy the Black Point for the next 2 nights.

DAY 3 Scarborough – Portland – Scarborough (15mi/24km)
This morning, take a short drive to Cape Elizabeth and visit the Portland Head Light & Museum, located along the spectacular shores of Fort Williams Park. The museum is located in the Keeper’s quarters. Then, it ’s on to Portland, an old seacoast town.Tour downtown’s Old Port historic district and some of the city’s historic homes. Portland is also a funky city filled with galleries, one-of-kind boutiques and shops, and incredible restaurants serving everything from New England clam chowder, lobster rolls and Maine seafood to nouveau cuisine.

DAY 4 Scarborough – Holderness, NH/Manor on Golden Pond (83mi/134km)
Head west through the Sebago Lakes Region to New Hampshire’s Squam Lake, best known from the movie “On Golden Pond” with Henry Fonda and Katherine Hepburn. Enjoy the next 3 nights at the Manor on Golden Pond. Reminiscent of its English heritage, the Manor’s fourteen-acre estate includes a host of recreational activities- tennis on clay court, croquet, badminton, and an over-sized swimming pool and pool cabana on top of Shepherd’s Hill overlooking Squam Lake.

DAY 5 Holderness – Franconia Notch – Mt. Washington – Holderness (71mi/114km)
Today, travel through Franconia Notch, which offers magnificent views and unique sites. Visit The Flume Gorge resplendent with the offerings of each season or take the aerial tram to the summit of Cannon Mountain. Continue further and board the Cog Railway to the summit of Mt. Washington. A ride up Mount Washington on the world’s first mountain climbing cog railway remains,as it has for well over a century, an exciting and unforgettable experience. 

DAY 6 Holderness 
Enjoy the Manor’s amenities. Down the terraced brick walkway and just across the road is their three acre sandy beach on the shores of Squam Lake where you can relax in the sun or have fun in one of the Manor’s canoes or paddleboats. If fishing is your sport, you’ll love the tranquility of this well-protected lake. You may choose to simply relax on one of those clear, spring, summer, or fall days in an Adirondack chair overlooking the lake and mountains. There are also wonderful areas in the Manor and fireplaces on chilly days where you can unwind with a good book or challenge your partner to a game of chess or backgammon. 

DAY 7 Holderness – Shrewsbury – Crisanver House (108mi/174km)
Scenic routes and covered bridges take you into Vermont. See Quechee Gorge, Vermont’s “Little Grand Canyon” before winding into Woodstock. A national magazine named Woodstock “The Prettiest Small Town in America” A lot of effort (and Rockefeller money) has gone into making sure the village keeps its pristine historic image. For instance, no utility wires appear overhead on downtown streets and the road you take to enter Woodstock will  either cross a covered bridge, pass a picturesque horse farm or country store, or wind along the Ottauquechee River. After enjoying lunch at one of its fine restaurants, head west across winding country roads, into Shrewsbury to enjoy 2 nights at the  Crisanver House.

DAY 8 Shrewsbury– Shelburne – Stowe – Shrewsbury (223mi/359lm)
Travel north along Vermont roads to visit the Shelburne Museum, one of the nation’s finest, most diverse, and unconventional museums of art and Americana. Over 150,000 works are exhibited in a remarkable setting of 39 exhibition buildings, 25 of which are historic and were relocated to the Museum grounds. Then, spend time in the charming village of Stowe, at the base of Mt. Mansfield. In  Waterbury, visit Ben & Jerry’s Ice Cream Factory for a tour and tasting before returning to Shrewsbury.

DAY 9 Shrewsbury– Williamstown – Deerfield, MA/ Deerfield Inn (117mi/188km)
Depart Shrewsbury and travel along Vermont’s scenic Route 7 toward Williamstown, MA, a quintessential New England village known for the beauty of its surrounding mountains, for Williams College, and for the cultural attractions of its Theater Festival and the Sterling and Francine Clark Art Institute. Choose to visit this museum and you will find an extraordinary collection of French Impressionist paintings,which take their place within a wider ensemble of masterworks that date from the Renaissance to the late 19th century and include an extensive collection of British and American silver. Continue into Stockbridge for the next 2 nights at the Red Lion Inn. This traditional inn, opened as a tavern in 1773, was rebuilt in 1897 after a fire destroyed the original structure. The Red Lion’s quintessential New England charm was immortalized by Norman Rockwell in his painting Stockbridge Main Street at Christmas.

DAY 10 Deerfield – Stockbridge – Deerfield (141mi/227km)
Take a morning trip through the Berkshires to Stockbridge, MA. Stroll this charming Dickensianstyle village and visit the Norman Rockwell Museum, housing the world’s largest and most significant collection of original Rockwell art. Highlights include enduring favorites from Rockwell’s Saturday Evening Post covers. Head back to Sturbridge and visit Old Sturbridge Village to relive 1830’s rural New England life at this living history museum.

DAY 11 Deerfield – Newport – Sandwich, MA/(207mi/333km)
Depart Deerfield for the coast of Rhode Island. Tour Newport’s Ocean Drive and Millionaire’s Row to see the magnificent mansions of the Gilded Age.Visit the Breakers, the largest of the Vanderbilt Family homes in Newport. Tour through the International Tennis Hall of Fame and enjoy lunch along the waterfront or at the historic Brick Marketplace. Before continuing to Cape Cod for the next two nights.

DAY 12 Cape Cod (117mi/188km) 
Today drive along the Cape Cod National Seashore to explore lighthouses, quaint coastal communities, and natural scenic beauty. Visit the lively artist colony of Provincetown, take a whale watch, or just lay on one of the Cape’s many sandy beaches. Don’t leave New England without feasting on Lobster, steamers, corn-on-the- cob and all the trimmings!

DAY 13 Sandwich – Plymouth – Boston (60mi/97km)
Depart Sandwich and head east to Plymouth, Massachusetts, “America’s hometown”. See Plymouth Rock, upon which the Pilgrims first stepped. Board a replica of the Mayflower, the ship which carried the Pilgrims to the New World and visit Plimoth Plantation, a recreated village of 1627, where “interpreters” bring history to life. After a leisurely lunch along the water, travel into Boston for your departure flight.
BostonFairmont Copley Plaza
Portland/ ScarboroughBlack Point Inn
HoldernessManor on Golden Pond
ShrewsburyCrisanver House
StockbridgeRed Lion Inn
Cape/SandwichBelfry Inne
Package includes 
  • Accommodations
  • Taxes
  • Fly-Drive Directions 
  • Information Packet at Hotel upon arrival