Southern New England &
The Hamptons of New York Fly Drive

Boston • Stockbridge • Hartford • Bridgeport • The Hamptons • Newport

Begin your holiday enjoying Boston’s lively neighbourhoods, discovering some of the city’s great restaurants and exploring Boston’s noted sites, architectural wonders, bustling waterfront, and magnificent museums.

Depart this bustling cosmopolitan city for quintessential New England and Connecticut villages steeped in the beauty of their surrounding mountains.

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 on-screen 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. 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.

There’s just time to visit Newport and along Ocean Drive and Millionaire’s Row to see the magnificent mansions of the Gilded Age and enjoy lunch along the waterfront before returning to Boston to finish the trip.

From €2957pp

What's Included

  • Return flights from Dublin to Boston
  • 11 NIGHTS hotel accommodation in selected fly drive hotels
  • Car Rental for full duration with fully inclusive insurance
  • Based on 2 adults sharing
  • 2018 Departure dates: April - Oct
  • Quote Ref 1532257

Staff Tips

Boston-For under $3, the Swan Boats driver paddles passengers around the Public Garden Lagoon for a 15 minute peaceful cruise.

Linda Collins

Travel Expert

We will arrange a flight to your destination where you pick up a rental car on arrival and tour at you own pace through your favourite destination. We can arrange all of your accommodation or you can ‘freelance’. Freelancing is not recommended during the park summer or autumn periods.

Kristin Skinner

Travel Expert

Your Adventure...

Boston Arrival
Boston
Boston – Williamstown – Lenox – Stockbridge
Stockbridge - Hancock - Stockbridge
Stockbridge - Litchfield County - Colebrook
Colebrook – Hartford – Colebrook
Colebrook – Bridgeport/Port Jefferson Ferry – Southampton
The Hamptons
Southampton – Orient Point/New London Ferry – Newport
Newport
Newport – Plymouth – Boston
  • Day 1 Boston Arrival

    Arrive Boston and transfer to your hotel. Evening on own to stroll Boston’s lively neighbourhoods 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

    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 Theatre 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

    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

    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. Its 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

    Enjoy the amenities of the inn, go antiquing or do some sightseeing 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 centre on social justice.

  • Day 7 Colebrook – Bridgeport/Port Jefferson Ferry – Southampton

    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 on-screen 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.

  • Day 8-10 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 Southampton – Orient Point/New London Ferry – Newport

    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 harbourfront.

  • 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

    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 Plymoth 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.

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