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Fly Drive USA

New England Charms

Begins in and ends in Boston, Massachusetts

  • 15 Days / 14 Nights
  • All year round

Concentrating on the southern New England states of Massachusetts, Rhode Island and Connecticut, this itinerary allows for longer in each location, so you have ample opportunity to discover the whole region. You’ll experience the charms of Boston, The Berkshires, Mystic Seaport, Danbury, New Haven, Newport and Providence. This itinerary includes:

  • Round-trip scheduled flights from London Heathrow to Boston, Massachusetts
  • Intermediate 4-door car hire including insurance
  • Accommodations as stated

Pricing Information

With airlines and hotels regularly introducing special offers, we’ve elected to not display pricing on our website. In order to ensure that we give you the most competitive price for the itinerary you’re interested in we’ll apply the best rates, promotions and offers that are available when we receive your enquiry. Please contact us via email, telephone or our websites ‘make an enquiry’, and we’ll endeavour to provide you with a tailor-made quotation within one working day.

Day 1

Arrive Boston

Depart the UK on your chosen scheduled flight to Boston. Upon arrival proceed to your hotel, the Fairmont Copley Plaza, your base for the first three nights. Located in the Copley area, a wide range of restaurants are close by where you can enjoy your first night in the city.

Fairmont Copley Plaza, Boston
Day 2, 3


Boston is a city rich in history and culture, so head out and explore. Take time to visit the waterfront, where seafood restaurants overlook the bustling harbour bringing the freshest ingredients to the table. From here you can take a whale watch boat tour or perhaps a catamaran trip out to the islands, and you can also find the city’s Aquarium. Follow the Freedom Trail, a walking route that starts at Copley Park and traces many historical attractions. Your hotel is located a few steps from the great shopping of Copley Place Mall and the eateries of Newbury Street.

Sightseeing in Boston

Fairmont Copley Plaza, Boston
Day 4


100mi / 161km

Today you collect your rental car and leave the big city behind. You’ll be heading for the pretty town of Deerfield, an authentic 18th-century New England village in the Connecticut River Valley. During your time here we recommend touring the beautifully restored museum houses with period architecture and furnishings. A visit to Deerfield is not complete unless you have explored the great outdoors and perhap partake in one of the activities available. The Channing Blake Footpath offers visitors the opportunity to discover Deerfield’s landscape or perhaps a trip to The Cooks’ Garden, a beautiful space that features plants that would have been used during colonial times.

The Deerfield Inn, Deerfield
Day 5, 6

Williamstown (The Berkshires)

45mi / 72km

After a hearty breakfast, today you will head for the picturesque town of Williamstown which will provide your base for the next two nights. Located in the Berkshires region of Massachusetts, Williamstown is a historic town where great art is housed in intimate settings. Hiking and biking trails abound in the Berkshires, which are famous for their gorgeous autumns. Summers in the Berkshires are just as enjoyable, though, as mild air and lush green hills provide a perfect pastoral backdrop to any outdoor excursion.

The Williams Inn, Williamstown
Day 7


126mi / 203km

This morning you have the choice of two routes down to Connecticut, you can take the beautiful scenic drive through the New England countryside, or perhaps take a slightly quicker way through New York State and then into Connecticut. Your base will be the town of Danbury where there is much to see and do. You could take to the water and enjoy swimming, boating or fishing at Candlewood Lake before taking in a Broadway performance at one of the many theatres in the evening. The downtown area of Danbury boasts luxury day spas and boutique shops should you need a little pamper or a spot of retail therapy. 

Ethan Allen Hotel, Danbury
Day 8

New Haven

35mi / 56km

Your next stop on this incredible journey is the port town of New Haven, home to famous Yale University, where the history of the campus oozes through every corner. During your time here be sure to stroll through the Chapel Historic District for an array of shopping options, art galleries, and live entertainment. For all history buffs, a visit to the Knights of Columbus Museum to see Catholic-focused exhibitions or perhaps the New Haven Museum for a deep look at this area’s rich history should be on your agenda.

Hotel Marcel, Tapestry Collection by Hilton, New Haven
Day 9, 10


55mi / 89km

Today you will make the short journey to the quintessential New England village of Mystic, a destination dominated by nautical landmarks and attractions. We have set aside two nights in this incredible area as it’s overflowing with must-see attractions to experience. Take time to explore the historic downtown and its quaint shops. Have your camera ready as the impressive Mystic River Bascule Bridge is raised. Eat, drink, and shop at the small stores in Olde Mistick Village. Spend some time exploring the hiking trails, exhibits, nature, and wildlife at the Denison Pequotsepos Nature Centre. Oh, and before you leave, be sure to get a picture at the cool wooden anchor in Liberty Pole Square. 

Sightseeing in Mystic

The Whaler's Inn, Mystic
Day 11, 12


46mi / 74km

It’s time to make your final border crossing into the small, but perfectly formed, state of Rhode Island. Your first stop is the stunning seaside town of Newport, where you will spend the next two nights of your adventure. Here you can explore miles of diverse shorelines, from exciting surf to lapping waves, lay on the beach, and soak up the sun or partake in many of the water sports activities including jet skiing, parasailing, windsurfing, scuba diving, or kite surfing. However, this town offers more than just water, with miles of paths and trails including the famed Cliff Walk with its prestigous mansions, the East Bay Bike Path, the Bay Walk, and more, seeing Newport on foot or on a bike is an eye-opening wonder.

Sightseeing in Newport

Newport Marriott, Newport
Day 13, 14


34mi / 55km

Today you will make the journey to your final destination. It’s just a 34-mile drive to Rhode Island’s capital city of Providence, where you will spend two nights. Scenically set upon three rivers, the downtown area of Providence offers a walkable riverfront in a bustling cityscape. A walk along Memorial Boulevard provides an opportunity to chart the city’s interesting architecture. If you’re travelling with family, be sure to spend a few hours at Roger Williams Park Zoo, a great family attraction with its waterways walks, botanical centre and Carousel Village. For something a little different, why not tantalize your taste buds on “The Hill,” a historic area that boasts many award-winning restaurants, or for a different perspective of Providence, take a romantic river cruise on an authentic Venetian gondola?

Sightseeing in Providence

Graduate Hotel, Providence
Day 15

Journey Home

53mi / 85km

This morning you may have time for some last-minute sightseeing or shopping for those all-important souvenirs, before making the 53 mile journey back to Boston International Airport to return your car and check-in for your flight to the UK. 

Get in Touch

Our team of travel professionals focus on providing you with the very best advice when it comes to planning your holiday to the USA and Canada. They have experienced the destinations, hotels, tours and excursions for themselves, so if its expert advice and guidance backed by faultless customer service that you are looking for, you couldn’t’ be in safer hands. We will listen to your wish list of ideas as well as add our own personal recommendations to create a unique itinerary, personalised just for you.

For a quotation based on your preferred travel date and to check availability please contact one of our team of professional consultants who will be happy to assist you.

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