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Boston, Massachusetts

Best of Massachusetts & The Berkshires Self-Drive

9-day tailor-made self-drive from £2,220 pp


Short description

Discover the rich history and postcard-perfect interior of America’s Bay State

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  • Explore Boston's unique heritage, showcased in cobblestone streets and winding laneways
  • Taste your way through the city's acclaimed culinary scene
  • Hit the open road to take in the revolutionary history of the Lexington battlefields
  • End with the tranquil beauty of the Berkshires, home to some of America's grandest estates

In Brief

  • 3 Nights Boston
  • 1 Night Salem
  • 1 Night Amherst
  • 2 Nights The Berkshires


Recommended for:
City | History & culture | Off the beaten track | Self-drive

America owes much of her early history to Massachusetts. After uncovering its revolutionary past in Boston’s historic sights and Lexington’s battlefields, you’ll be treated to the same scenery that greeted the pilgrims some 400 years ago in the Berkshire Hills. Now the playground for the rich and famous, their verdant geography is home to pretty estates, idyllic walks and manicured golf clubs. In between, you’ll trace a more chequered past in Salem’s witch hunts after spending some time to familiarise yourself with the state capital’s art museums, world-beating universities and love of all things cultural.

Day by day itinerary

Day 1

Relax with included airport lounge access before a daytime flight brings you to the site of America’s modern foundations – Boston. On arrival, make your way to your luxury hotel. Positioned in the historic Back Bay district just steps from Beacon Hill and the esplanade, Fairmont Copley Plaza has played host to almost every past president since its 1912 opening. Rooms are lavish and the excellent fine dining restaurant is complemented by a cocktail bar and rooftop health club.

Stay: Fairmont Copley Plaza, Boston (Deluxe)

Days 2-3

Sometimes known as ‘the walking city’, it’s possible to quite literally follow in the footsteps of Boston's storied past. On the Freedom Trail, a two and a half mile route leads you to museums, two-hundred-year-old frigates, 19th-century state houses and meeting houses where the fate of the nation was decided. Elswhere, manicured green spaces abound while crossing over into nearby Cambridge brings you to its intellectual powerhouses. In Harvard, you’ll find a redbrick, leafy campus with excellent museums open to the public and, in MIT, there’s a university leading the way in scientific discovery. There’s also the superb New England Aquarium along with the Museum of Fine Arts where contemporary experiments rub shoulders with European classics.

Stay: Fairmont Copley Plaza, Boston (Deluxe)

Day 4

Today, after collecting your hire car, you’ll make the one-hour drive up the coast to Salem. Look past its infamous 17th century witch trials – immortalised in restored examination rooms and Halloween parades – and you’ll find a relaxed, seaside town still living off its maritime past. Once the centre of America’s clipper-ship trade with the Orient, you’ll find historic wharves lined with 19th century lighthouses and tall-ships best experienced in the Salem Maritime National Historic Site.

Stay: Salem Waterfront Hotel & Suites (Superior)

Day 5

Next, you’ll make the short drive along the brilliantly named Yankee Division Highway back inland to well-heeled Lexington in the countryside just outside of Boston. This is country club America at its finest with pretty Victorian neighbourhoods and giant lawn-ringed mansions. You’ll also find a revolutionary past, best seen in the Lexington Battle Green where the first shots of that country-defining event were fired. Cemeteries and colonial houses bear further witness to its significant past. This afternoon, continue on to the college town of Amherst where you'll spend the night.

Stay: Inn on Boltwood, Amherst (Superior)

Days 6-7
The Berkshires

On your sixth day you’ll strike into Massachusetts’ green interior on a two to three hour drive into the heart of the Berkshire Hills. Long the retreat for the elite of Boston and New York, grand estates dot its picturesque undulations of forests and meadows. You’ll stay in the small town of Lenox, at a grand country house host to cosy lounges, roaring fires, an indulgent spa and delicious farm-to-table food.

Stay: Kemble Inn, Lenox (Deluxe)

Day 8
Depart Boston

For your penultimate day, you’ll make the short drive back through the winding countryside to Boston’s international airport. Drop off your hire car and board your overnight flight home, arriving back in the UK on day 9.

Day 9
Arrive UK

Arrive back in the UK after your overnight flight and continue your onward journey home.



Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

Accommodation rating: Superior Deluxe

9-day tailor-made self-drive from £2,220 pp

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At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

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