Though New England holidays are famous for the Fall colours, the region bursts into life in summer. This leisurely journey across southern New England takes you through coastal villages, arty towns and majestic ancient forests, stopping in the charismatic city of Boston along the way. Enjoy fabulous food and wine at the region's best restaurants, and sail along the coast for America's most beautiful sunsets.


  • Fine wine and dining in the Connecticut River Valley
  • Beautiful sunsets and seafood dinners on Martha's Vineyard and Cape Cod
  • Mooching around historic fishing villages and whaling stations
  • Exploring the individual, muscular city of Boston
per person

Price from

Destination Expert Mel Matthews


North America Specialist


  1. Arrive
  2. Day 1 - 2 Litchfield County, Connecticut

    The beautiful Litchfield Hills in Connecticut are driving distance from both New York and Boston, so you can choose where you fly into (although the journey from New York is easier). We will organise a rental car for you to make your own way. Winvian lies on a large estate and offers charming individual cottages, an excellent spa and five-star cuisine. The area is known for its prestigious mansions, walking trails and for the food and wine tasting on offer in the Connecticut River Valley.

    Overnight: Winvian, Connecticut

  3. Day 3 - 4 Newport, Rhode Island

    Heading north east will bring you into Rhode Island and the historic coastal city of Newport, which claims to be the yachting capital of the world. Naturally, chartering a yacht for the day is highly recommended. Or alternatively you can try your hand at ship building at the Newport Shipyard. The fly fishing and white-water rafting on the Housatonic River is very good, and we recommend getting back in time for a rum-making class with a Newport expert in time for a sunset cocktail.

    Overnight: The Vanderbilt Grace

  4. Day 5 - 6 Cape Cod

    Drive from Newport to Cape Cod, the claw-like peninsula south-east of Boston. Known as a long-standing holiday favourite, quaint Cape Cod is a place of simple pleasures - lazy days at the beach, saltwater taffy, seafood snacks from roadside shacks, and unpretentious people and places. It is a lovely place to spend time by the sea and enjoy delicious New England seafood staples washed down with local craft beer.

    Overnight: Chatham Bars Inn

  5. Day 7 - 9 Nantucket, Massachusetts

    Drop off your rental car in Hyannis and catch a short flight to Nantucket, 30 miles off the coast. After checking-in to your hotel, enjoy a cycle tour to see the old whaling captain's stately home before a cruise around the coast at sunset. You will be spoilt come dinner-time, as Nantucket has some fantastic seafood restaurants on the waterfront.

    Overnight: White Elephant Hotel

  6. Day 10 - 12 Martha's Vineyard

    Perennial summer favourite, Martha's Vineyard lies just a short flight from Nantucket, a haven of beaches and sleepy historic towns. Once on the island, we recommend hiring a car so you can get around easily, but today your guide will meet you on arrival and take you on a tour of Edgartown, Oak Bluffs, Chillmark and Tisbury. The peaceful fishing village of Menemsha has supposedly one of the most beautiful sunsets in America.

    Overnight: The Charlotte Inn, Edgartown

  7. Day 13 - 14 Boston

    Drop your car off and take a quick flight from 'The Vineyard' to Boston. After your time relaxing and rejuvenating by the coast, it's time to make the most of the city. Boston has a proud history and a unique character. Be sure to take a historian's tour around the sights, check out the nightlife and maybe head to a ball game; we can even organise a behind-the-scenes tour of Fenway, home to the Boston Red Sox.

    Overnight: Four Seasons, Boston

  8. Day 15 Fly home

    Bid New England farewell and head to the airport for your return flight.

  9. Depart


Low £ 4,500 $ 6,112
Mid £ 4,950 $ 6,723
High £ 5,600 $ 7,606


  • Based on two people sharing a twin/double room throughout.


  • All accommodation as detailed in the itinerary.
  • Daily breakfast.
  • Private transfers throughout.
  • All sightseeing, entrance fees and guide services as detailed in the itinerary.
  • Internal flights where detailed in the itinerary.


  • International flights.
  • Meals not indicated in the itinerary.
  • Items of a personal nature such as laundry, drinks, gratuities (discretionary).
  • Entrance fees and excursions not specifically mentioned as included.
  • Travel insurance or visa fees.

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