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Discover the tastes of Massachusetts and New England on this self drive tour, this tour takes you through some of lesser known areas to experience the real craft beer industry combined with the natural beauty of the New England area. You’ll be exploring four of the New England states. From the beauty of Maine’s rocky coastline, to the mountains of New Hampshire and Vermont. Explore Hyannis, visit the John F Kennedy Hyannis Museum, or take the ferry to Nantucket.  Walk the historic streets of Boston, dine with the locals at Faneuil Hall Marketplace or even watch the Boston Red Sox at Fenway Park. This self drive will leaving you wanting to explore more of New England.


11 Days

Guide Price

£2,399 pp

Recommended For

City, Couples, Culture, Fly Drive, Self Drive, USA Road Trips


Private basis

a bridge over a body of water with a city in the background

Trip Highlights

  • Sample the local beers throughout your journey
  • Enjoy a concert in Tanglewood
  • Visit Sam Adams brewery for a tour and tasting
  • Enjoy the photo opportunities of covered bridges, white steeple churches and Mountains

Start your Journey

Day 1

Boston to Portsmouth

Room Only

After arriving into Boston and picking up your car hire. You'll head north to Portsmouth, a port city with cobblestoned streets, a downtown filled with charming shops and restaurants, significant examples of Colonial, Georgian, and Federal style houses, and brewers who continue New England’s rich beer-making history. 

  • Suggested Accommodation Sheraton Portsmouth or similar
Day 2 - 3

Portsmouth to Bar Harbor

Room Only

This morning before you start your drive along the coastal route from Portsmouth to Bar Harbor, to the Red Hook Brewing Company to find out about their local brews. Once your en-route to Bar Harbor stop in the largest city within Maine Portland, head to the Old Port to take a stroll through the bustling shops. Pick and chose which coastal towns you stop at as you continue your adventure.

The next day explore "Millionaires Row", sample the local craft beer at Atlantic Brewing Company and make sure you eat the local seafood caught fresh that day. 

  • Suggested Accommodation Atlantic Oceanside Resort or similar
Day 4

Bar Harbor to North Conway to Jackson

Room Only

Travel along the winding roads to North Conway which is located on the edge of the White Mountains. Maybe take the 13 kilometre Mount Washington Auto Road, which leads straight up to the mountain observatory or let someone else do the driving by hopping on the Conway Scenic Railroad and take a ride past the stunning bluffs, ravines and streams of Crawford Notch. When you arrive in Jackson you'll be welcomed by lots of photo opportunity of covered bridges, white steeple churches and stunning  mountains.

  • Suggested Accommodation Christmas Farm Inn or similar
Day 5 - 6

Jackson to Essex Junction

Room Only

Spend the morning exploring the White Mountains, this includes part of the part of the famous Appalachian Trail. As you head to Essex Junction stop and try sugar snow at Morse Farm , explore Shelburne Museum's art and american exhibits.

The following day stop by for a visit to the Rock Art Brewery and Magic Hat Brewing company to taste the local beer. Don't forget Ben and Jerry's Ice Cream Factory in Stowe.  

  • Suggested Accommodation Essex Vermont's Culinary Resort or similar
Day 7

Essex Junction to North Adams

Room Only

Drive the scenic route to the Berkshires, enjoy the sparkling lakes, lush woodlands and fresh mountain air, the Berkshires attracts artists of all types looking for inspiration and rejuvenation. Visit the Clark Art Institute to witness this for yourself. Check out a local concert in Tanglewood. Tanglewood is a music venue in the towns of Lenox and Stockbridge in the Berkshire Hills, the summer home of the Boston Symphony Orchestra, 

  • Suggested Accommodation Porches Inn at Mass Mo CA or Similar
Day 8

North Adams to Hyannis

Room Only

This morning explore MASS MoCA, housed on a restored 19th century factory campus, this is the largest centre for contemporary visual and performing arts in the country. Today your heading to the Cape, into Hyannis. Explore the Cape Cod Rail Trail, hire a bike and take a leisurely cycle past cranberry bogs and lakes. Stop for lunch and enjoy the fresh abundance of local sea food.

  • Suggested Accommodation Cape Codder Resort & Spa or similar
Day 9 - 11


Room Only

Today you leave Hyannis and head to Wood Hole to board a ferry for the day to Nantucket. Explore the cobbled streets and stately homes of this once prosperous whaling port. We recommend leaving your car at Woods Hole and exploring the dune fringed coastal trails and pathways by hiring a bike. Take the afternoon ferry back to collect your car, to make your way to Boston.

The next morning follow the Freedom Trail, the trail covers 2.5-mile route that takes you to 16 important sites during the American Revolutionary War. You can either start or end the walk at the Boston Common or at the USS Constitution and Bunker Hill. Along the walk, you will visit historic churches, meeting halls, cemeteries, and battlegrounds. Be sure to visit and take in the architecturally significant Back Bay, and bustling waterfront. Boston continues to be an important centre of commerce, technology, and the arts for both the region and the country. Be sure you book yourself a tour of the Sam Adams Brewery, before your self drive holiday comes to an end, 

  • Suggested Accommodation Wyndham Boston Beacon Hill or similar

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