The Green Mountains, Vermont
The Green Mountains, Vermont
Scenery in Boston, Massachusetts
Scenery in Boston, Massachusetts
Portlant, Portsmouth & Kennebunkport
Portlant, Portsmouth & Kennebunkport
The Green Mountains & Kancamagus
The Green Mountains & Kancamagus
Hyannis & Cape Cod
Hyannis & Cape Cod

Self-Drive New England Back Roads

7 nights from €989 per person Including Flights


This unforgettable driving tour will take you on a journey through Boston’s most historic sites, along the wild and rugged Maine coast, through the heart of New England most jaw-dropping mountain scenery to Cape Cod’s glorious white sand beaches and picturesque lighthouses, capturing the very best this region has to offer. (TMAP/TM)


  • Enjoy exploring Boston’s most iconic sights
  • Dine on lobster at Kennebunkport, Maine’s famous Dock Square
  • Hop on the aerial tramway at Franconia Notch State Park to take in jaw-dropping views from the summit of Cannon Mountain
  • Visit famous New England museums and the Hancock Shaker Village for a close-up look at a fascinating utopian society
  • Learn about history from “Pilgrims” on the Mayflower, stroll beautiful Cape Cod beaches and watch humpback whales leap from the Atlantic waters

Itinerary Overview

Fly into Boston 1 night – South Portland 1 night – North Conway 1 night – Killington 1 night – Lenox 1 night – Hyannis 2 nights – Fly home

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • CAR licensed & bonded
  • In resort assistance & 24 hour contact centre
Why Book with American Sky?
  • Hassle-free - book direct quickly and easily
  • 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
  • No amendment fees
  • Low deposits
Why American Sky?
Your money is safe We safeguard your money with ATOL protection and have membership to codes of best conduct.
Why American Sky?
Award Winning
We answer quickly On average, calls are answered within three rings. We also respond within hours to emails.
Why American Sky?
Award Winning
We offer expert advice and great service Our luxury tailor-made holidays are created with impeccable service from start to finish.

Day 1

Boston, MA

New England’s largest city is highly navigable, clean and home to a rather astounding number of historical sites along with plenty of modern delights that make it an ideal destination for all types of travellers. Whether you’re a history buff, a museum lover, avid shopper, food enthusiast, or all of the above, Boston is sure to intrigue and enchant. Taking a stroll along the 2.5-mile redbrick Freedom Trail from Boston Common to Bunker Hill is a must. You’ll travel through the city’s most historic neighbourhoods, with 16 important sites pertaining to the Revolutionary War to experience along the way, including the Old North Church, the very spot where Paul Revered warned that the British were coming in 1775, sparking the American Revolution. Visit the Old State Museum where you can explore impressive memorabilia like the vial of tea that was salvaged from the original Tea Party crowd, and when you’re in need of a break from all that history, do some shopping at Faneuil Hall Marketplace. Grab a bite beneath the Quincy Market canopies when hunger hits, and then take in a street performance or two before returning to the trail. Some of the other highlights to consider include a visit to the Institute of Contemporary Art or the Museum of Science, cheering along with Red Sox fans at Fenway Park, touring Sam Adams Brewery and people watching along the Charles River Esplanade.

Standard Hotel: Midtown Hotel
Superior Hotel: Courtyard Tremont

Day 2

South Portland, ME (95 miles)

Travel from Boston to South Portland, Maine, stopping in Portsmouth, New Hampshire to enjoy tax-free shopping, historic sites, museums and eateries with waterfront views before taking the coastal road to York and Ogunquit, stretching your legs on the Marginal Way walking trail that stretches 1.25-miles from Perkins Cove, taking in some of New England’s most iconic scenery. Continue to Kennebunkport, stopping for legendary lobster at Dock Square before moving on to your final destination for the night, South Portland.

Standard Hotel: Best Western Merry Manor Inn
Superior Hotel: Harraseeket Inn, Freeport

Day 3

North Conway, NH (65 miles)

Start your morning by exploring the historic Old Port District, Portland’s shopping mecca, with its cobblestone streets lined with antique shops, chocolatiers, gourmet and souvenir shops, clothing and jewellry stores, and more. When you’ve had your fill, head to Jackson, with stops at Sebago Lake, Maine’s deepest and largest lake, and Moose Pond, famous for its striking scenic beauty at the base of the Shawnee Peak.

Standard Hotel: Green Granite Inn
Superior Hotel: Christmas Farm Inn (Jackson, NH)

Day 4

Killington, VT (134 miles)

The next 134-mile leg of the journey will take you to Killington, Vermont, including a scenic drive along Northern New Hampshire’s Kancamagus Highway, a 34.5-mile route that’s been designated an American Scenic Byway thanks to its spectacular beauty, rich history and culture. It boasts breathtaking views of the White Mountains, waterfalls and Rocky Gorge. Get ready for a photo-op just outside Lincoln, where you’ll pass through Franconia Notch, a mountain pass with soaring mountains that rise as high as 3,000 feet on each side. Flume Gorge is an ideal place to get re-energised as you walk through the natural gorge with walls of towering granite and lush greenery. Take the aerial tramway in Franconia Notch State Park to the top of Cannon Mountain for more awe-inspiring vistas from the 4,080-foot summit before reaching today’s final destination.

Standard Hotel: Killington Mountain Lodge
Superior Hotel: Trapp Family Lodge (Stowe, VT)

Day 5

Lenox, MA (130 miles)

Travelling through the heart of New England from Killington to Lenox, Massachusetts, you’ll pass through the picturesque Berkshire Hills, legendary for brilliant autumn foliage, before stopping in Williamstown, home to famous art museums, including Café 7, an art museum/research centre where you can also grab a bite for lunch.

Before coming to your final destination for the night, visit Hancock Shaker Village for a glimpse at the inner workings of a fascinating utopian society that existed before the industrial revolution, and the Norman Rockwell Museum in Stockbridge to view an impressive collection of Rockwell’s original works, his study and personal memorabilia.

Standard Hotel: Best Western Plus Berkshire Hills
Superior Hotel: Williams Inn (Williamstown, MA)

Day 6 & 7

Hyannis, MA (150 miles)

Today’s adventure will lead you to some of America’s most famous historic sites and some of New England’s most picturesque landscapes, culminating in Hyannis on Cape Cod. History truly comes alive at Old Sturbridge Village, where you’ll step back into life during the early 19th-century, exploring more than 40 historic buildings from a magnificent church, schoolhouse and pottery shop, to homes, stores, and more. Just before crossing the Sagamore Bridge onto Cape Cod, is the village of Plymouth, best known as the site of the landing of the Pilgrims who were fleeing religious persecution in Britain. View Plymouth Rock, which marks the spot of their landing, and then hop aboard the Mayflower, a full-scale replica of the original ship, to take a tour led by informative and entertaining costumed guides.

Upon awaking in Hyannis, you can look forward to a day of exploring the Cape, including the beautiful Cape Cod National Seashore which stretches for miles along the north end. Stroll across the high cliff dunes, join a guided walk or a kayak tour before visiting any one of the 16 lighthouses here, like the Highland Light, one of the oldest and tallest on the Cape. Enjoy some of America’s best antique shopping, as well as browsing boutiques and galleries, before embarking on a whale watching adventure in Provincetown, with humpback and fin whales regularly spotted, along with seals and dolphins.

Standard Hotel: Heritage House Hotel
Superior Hotel: Hyannis Harbor Hotel

Day 8

Boston, MA (70 miles)

Before returning to Boston, enjoy relaxing and preparing for your journey home – or the next leg of your adventure, wherever your travels might take you.

  • 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
  • Electronic roadbook

What's not included

  • Parking fees
  • Attractions and excursions

Rachel McAnaspie
Book today

Talk to our travel experts for more information and to book or tailor-make your holiday

01 6649900 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun

American Sky also recommends