Rocky coastline in Maine, Massachusetts
Rocky coastline in Maine, Massachusetts
Portsmouth Waterfront & Portland Head Lighthouse
Portsmouth Waterfront & Portland Head Lighthouse
The White Mountains, New Hampshire
The White Mountains, New Hampshire
Stowe, The Green Mountains & Quechee, Vermont
Stowe, The Green Mountains & Quechee, Vermont
Cliff Walk in Rhode Island, and Cape Cod beachfront and waterfront
Cliff Walk in Rhode Island, and Cape Cod beachfront and waterfront

Self-Drive Inn-Side New England

12 nights from £2,089 per person Including Flights


This self-drive tour will take you from Boston to the charming coastal towns of Maine and inland to the spectacular New Hampshire Lakes region and the lush hills of Vermont, with its lovely covered bridges. Enjoy a bit of history, plenty of outdoor adventure, and even ice cream tasting on the famous Ben & Jerry’s Factory tour, before heading back to the coast and enjoying some of the best Cape Cod has to offer. (TMAP/TM)


  • View the famous Portland Head Light and take the scenic cliff walk, meandering along the Maine Atlantic
  • Ride the Cog Railway to the summit of Mount Washington and hike the scenic trails in White Mountain National Forest
  • Take the Ben & Jerry’s factory tour, visit the Norman Rockwell Museum and explore a former Shaker community for an authentic look at Shaker life
  • Tour the grand mansions of Newport, Rhode Island, visit the Tennis Hall of Fame and immerse yourself in beach life on Cape Cod
  • Hop aboard a whale watching boat from Provincetown and explore historic sites in Plymouth, including Plymouth Rock, the Mayflower and Plimouth Village, a living history museum

Itinerary Overview

Fly into Boston 1 night – Scarborough 2 nights – Jackson 3 nights – Shrewsbury 2 nights – Stockbridge 2 nights – Sandwich 2 nights – Fly home

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • ATOL protection
  • In resort assistance & 24 hour contact centre
Why Book with American Sky?
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  • Choice of airlines and the option to switch
  • A friendly, family run business with a wealth of experience.
  • Great deals on offer for multiple destinations
  • Low deposits
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Day 1

Boston, MA

Arrive into Boston and check into your hotel.

Overnight: Boston Park Plaza or simlar

Day 2 & 3

Scarborough, ME (129 miles)

As you make your way from Boston to Scarborough, take time to enjoy the charms of the small coastal towns along the way, stopping in historic Portsmouth, founded in 1623 as one of the nation’s oldest cities. Dine at one of the waterfront eateries, do some tax-free shopping or check out USS Albacore Museum, housed in a 1953 US Navy submarine. Stretch your legs in Ogunguit on Marginal Way, a scenic cliff walk that meanders along the ocean for more than a mile along the coast, ending in Perkins Cove, before reaching your final destination for the next two nights.

Enjoy Day 3 in Portland, just a short drive from Scarborough, where you can view the historic Portland Head Light, an iconic landmark that sits along the shores of Fort Williams Park. Enjoy stunning Atlantic views and explore the museum, contained within the former Keepers' Quarters, where lighthouse lenses, interpretative displays and a seasonal gift shop are located. Afterwards, visit Downtown Portland, known as the Old Port. This walkable neighbourhood is bursting with excellent restaurants and bars, contributing to Portland’s growing reputation as a foodie’s delight.

Overnight: Black Point Inn or similar

Day 4, 5 & 6

Jackson, NH (80 miles)

Next you’ll embark on a short but scenic drive, traversing along Sebago Lake, Maine’s deepest and largest lake, and the New Hampshire Lakes region, home to 273 lakes and ponds, before settling into Jackson for three nights. This picturesque village makes an ideal base for taking advantage of all the White Mountains have to offer.

Head to Franconia Notch in the heart of the White Mountain National Forest, a breathtaking mountain pass traversed by a unique parkway that extends from the Flume Gorge. Walk through the renowned Flume Gorge, a natural gorge with walls of Conway granite that soars to a height of up to 90 feet, and then ride the Cog Railway to the top of Mount Washington to take in the view from New England’s highest peak. On your last day in Jackson, you might want to relax at your hotel, but if you have energy to spare, hike one of the many spectacular trails in the White Mountain National Forest. You’ll find everything from short treks that, for minimal effort, can take you to a waterfall or an awe-inspiring view, as well as longer hikes to scenic outlooks, lakes and ponds and mountain summits.

Overnight: The Wentworth or similar

Day 7 & 8

Shrewsbury, VT (155 miles)

Today you’ll drive to Shrewsbury, Vermont, and make a couple of stops along the way. Visit Quechee Gorge, known as Vermont’s Little Grand Canyon and the state’s most impressive natural wonder. Marvel at the gorgeous views overlooking the Ottaquechee River and walk the trails along the mile-long chasm. By following the network of trails that parallels the river downstream, you’ll be able to see the magnificent cascading falls. Just a short drive away is Woodstock, an ideal destination for shopping and grabbing a bite to eat. This shire town exudes Americana charm as a quintessential New England village with a picturesque covered bridge, old country farms, pretty parks, restored Georgian, Federal and Greek Revival homes, a village green and a number of outstanding eateries and shops.

In the morning, it’s time to explore the area’s delights, including the Shelburne Museum of Art & Americana, one of the nation’s most diverse museums of folk art, paintings, quilts and textiles, as well as New England history and architecture. You’ll want to get your camera out frequently for the charming town of Stowe, a postcard-perfect village with covered bridges and church steeples set against the lush Green Mountains. Of course, you won’t want to miss your chance to enjoy any ice cream lover’s favourite: the famous Ben & Jerry’s Factory Tour where you’ll earn how this tasty treat is made, as well as enjoy plenty of delicious samples.

Overnight: Crisanver House or similar

Day 9 & 10

Stockbridge, MA (104 miles)

Stockbridge, Massachusetts is up next, but first is “the Clark,” The Sterling and Francine Clark Art Institute in Williamstown with an extensive collection that includes European and American paintings, sculpture, prints, drawings, photographs, and decorative arts from the 14th- to the early 20th century. At the nearby Hancock Shaker Village, a former Shaker community, you’ll get an authentic looks at Shaker life and find out why the villagers referred to it as the “City of Peace.” Your final destination for the next two nights is well-known as the birthplace of Norman Rockwell. Visit the Norman Rockwell Museum to view an impressive collection of Rockwell’s original works, his study and personal memorabilia. Take time to stroll through this quintessential New England town too, with its grand homes and beautiful gardens.

Overnight: Red Lion Inn or similar

Day 11 & 12

Sandwich, MA (176 miles)

Today’s journey will bring you to the hook-shaped peninsula known as Cape Cod. First, prepare to be wowed by the Newport Mansions in Rhode Island, the homes of the elite during the Gilded Age. There are 10 open for tours, including the Breakers, the grandest of them all with more than 65,000 square feet of indoor space and a perfectly manicured 13-acre lawn overlooking the Atlantic. Afterward, explore the International Tennis Hall of Fame, and then enjoy dining at one of the oceanfront restaurants that focus on the spoils of local fishermen and farms to create classic New England cuisine.

Continuing onto Cape Cod, you’ll be perfectly situated for exploring the Cape Cod National Seashore with its alluring dunes set at the edge of the Atlantic. Gaze out at the ocean and then get out on the water by visiting the artist colony of Provincetown to embark on a whale watching trip from the northern tip of the Cape.

Overnight: Belfry Inn or similar

Day 13

Sandwich, MA (60 miles)

There’s lots to look forward to on your final day too, with a stop in Plymouth, famous as the site of the landing of the Pilgrims, before returning to Boston. This is your chance to see the iconic Plymouth Rock that marks the spot of their landing, hop aboard a full-scale replica of the Mayflower and visit Plimouth Plantation, a living history museum, where you can experience this area just as it was back in the 17th century.

  • Return transatlantic flights
  • Economy size car hire retual including fully comprehensive insurance (upgrades available)
  • Hotel accommodation as described above or similar on a room only basis

What's not included

  • Parking fees
  • Attractions and excursions

Holly Reid
Book today

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