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Southern New England and the Hamptons of New York
DAY 1: Boston
Arrive Boston and transfer to your hotel. Evening on own to stroll Boston’s lively neighborhoods and discover some of the city’s great restaurants.

DAY 2: Boston
Explore Boston’s noted sites, architectural wonders, bustling waterfront, and magnificent museums. Choose to take a whale watch, walk around Harvard yard in Cambridge or join a day tour to the historic battlefields of Lexington and Concord.

DAY 3: Boston – Williamstown – Lenox – Stockbridge (202mi/325km)
Depart Boston for 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. In Lenox, see Tanglewood, the Boston Symphony’s summer home before ending the day in the charming Dickensian village of Stockbridge.

Day 4: Stockbridge – Hancock – Stockbridge (52mi/84km)
Today, visit the Norman Rockwell Museum in Stockbridge, which houses his paintings of America past. Highlights include paintings from Rockwell’s Saturday Evening Post covers. Then, tour Hancock Shaker Village, This beautifully restored village, set on 1,200 acres of farm, woodland and pasture, is home to the premier collection of Shaker buildings and artifacts.

Day 5: Stockbridge – Litchfield County – Colebrook, CT (39mi/63km)
Travel through the beautiful Litchfield Hills of Connecticut. This northwest corner of the state offers an extraordinary collection of antique shops, intriguing small museums and exceptional restaurants. It’s natural beauty lends itself to a wide variety of year-round recreational opportunities from skiing and canoeing to fly fishing and horseback riding. Overnight in one of the region’s incomparable inns.

Day 6: Colebrook – Hartford – Colebrook (62mi/100km)
Enjoy the amenities of the inn, go antiquing or do some siteseeing in nearby Hartford. Here, one can visit the Mark Twain House. Mark Twain and his family lived in this 19- room mansion from 1874-1891, or visit the Harriet Beecher Stowe Center. Stowe was the author of the anti-slavery novel Uncle Tom’s Cabin and tours are given of her home, gardens and center on social justice.

Day 7: Colebrook – Bridgeport/Port Jefferson Ferry – East Hampton, NY (135mi/217km)
Take the short drive to Bridgeport and drive onto the ferry to Port Jefferson on Long Island. One hour and 20 minutes later arrive Long Island and continue east into the Hamptons. The Hamptons are a popular seaside resort, making up the villages on the most eastern part of Long Island. It has some of the most expensive residential properties in the U.S. and it is frequently featured onscreen and mentioned in films and television. The Hamptons history, beautiful gardens, arts, culture, and its’ beautiful beaches draw the affluent from NYC and surrounding states.

Days 7 – 10: The Hamptons
Relax here for the next few days, taking in all this iconic destination has to offer. Visit the wineries, go horseback riding, stroll the charming villages filled with boutique shops and art galleries, have a picnic at an outdoor concert, tour the historic mansions, or just relax on the beach.

Day 10: East Hampton – Orient Point/New London Ferry – Newport (95mi/153km)
Drive aboard two shuttle ferries before arriving at Orient Point for the ferry to Connecticut. Upon arrival, transfer to Newport, famous as the crown jewel of the southern New England coastline and the home of Gilded Age mansions that once were the summer playground for socialite families with names like Astor and Vanderbilt. This afternoon visit some of the downtown and waterfront’s historic sites. Touro Synagogue- the first synagogue in the United States, and the Old Stone Mill – its origin unknown, there are several theories as to its historical use and significance. This evening, dine along Newport’s beautiful harborfront.

Day 11: Newport
Today, tour along 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.

Day 12: Newport – Plymouth – Boston (98mi/158km)
This morning, depart for 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.


XV Beacon


The Stockbridge Inn


Rock Hall


Southampton Inn


Vanderbilt Grace

Package includes:
  • Accommodation
  • Taxes
  • Passenger and vehicle fare for the Port Jefferson and Orient Point Ferries
  • Fly - Drive directions and information packet at hotel upon arrival