Autumnal road landscapes in New England
Autumnal road landscapes in New England
Boston, Kennebunkport & Portland scenery
Boston, Kennebunkport & Portland scenery
Arcadia National Park & The White Mountains in New Hampshire
Arcadia National Park & The White Mountains in New Hampshire
Stowe in the Autumn
Stowe in the Autumn
Cape Cod & Martha's Vineyard
Cape Cod & Martha's Vineyard

Experience New England Self-Drive

10 nights from €1,529 per person Including Flights


You will see all the highlights of New England on this self-drive itinerary for 10 nights. Enjoy the coastline of Maine and Cape Cod, feast on lobster and maybe go whale-watching. Head for the rolling hills of picture-perfect Vermont. Enjoy spectacular views from the summit of Mount Washington. You can make this holiday as relaxing or as active as you want – either simply admiring the stunning views, or hiking and biking through the lovely countryside. (TM)


  • Sample the local lobster in coastal Maine, and perhaps take a trip on a lobster boat
  • Drive to the top of the highest peak in North East USA – Mount Washington
  • Explore rural Vermont, and enjoy the charming towns and picturesque countryside
  • Spend time on the beautiful beaches of Cape Cod, visit the chic retreat of Martha’s Vineyard.

Itinerary Overview

Fly into Boston 1 night – Mid Coast Maine 2 nights – White Mountains 2 nights – Vermont 2 nights – The Berkshires 1 night – Cape Cod 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
  • Low deposits
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Day 1

Arrive Boston

Fly into Boston. For this itinerary, we have suggested you head straight into the heart of rural New England, but you may want a couple of nights in Boston to have chance to experience this great city with a fascinating history and charming neighbourhoods.

Day 2

Boston - Mid-coast Maine (110 miles)

Travel north up the coast into the New England state of Maine. There are several lovely resorts and towns to stay Mid Coast Maine, you can either  stay in quaint Kennebunkport, where you’ll find the quirky Seashore Trolley Museum with its huge collection of streetcars, plus historic churches and lighthouses. Or head for Portland, where you will find working fishing wharves and converted warehouses with restaurants and shops, and in the West End district  Victorian-era homes including the Victoria Mansion museum.

Day 3

Mid Coast Maine

Enjoy a day in this lovely coastal region. Stroll the beautiful beaches, taking in the stunning seascapes. Perhaps take a lobster boat tour, to learn all about this industry and of course taste the wonderful produce. You’ll be spoilt for choice with seafood restaurants, plus many other cafes and restaurants offering “Farm to Fork” food in this richly rural region.

Day 4

Mid Coast Maine - White Mountains (65 miles)

For this itinerary, we’ve planned for you to head inland and leave the coast behind. But if you have more time, you might like to journey further north along the coast into the Arcadia National Park, and the lovely coastal town of Arcadia. Just ask if you would like more details.

Leave Maine for the state of New Hampshire, driving through fields into forests and up into the White Mountains, which cover about a quarter of the State. Admire the  towering peaks and spectacular waterfalls. You’ll be spending two nights in this region, so keep your camera handy to take some memorable shots.

Day 5

White Mountains

Our suggestion for today is to drive up to the summit of Mount Washington – the highest peak in the North East at over 6,000 feet. The road to the top is usually open mid-May to Mid-October . There you will find a weather station and Extreme Mount Washington museum, housed inside the Mount Washington State Park Sherman Adams Visitor Center. Or you could take the Cog Railway to the top – a guided three hour adventure.

Day 6

White Mountains - Vermont (120 miles)

Time to head into perhaps the most well-known state of New England – Vermont. Famous for the colourful autumn foliage, this region is charming and picturesque at any time of year. Drive to the gorgeous town of Stowe in the very heart of Vermont. There are several accommodation options but we love the Trapp Family Lodge for the characterful comfort and the wide range of activities available. And of course, it is run by the real-life Von Trapp family, whos escape from Austria was immortalised in the film The Sound of Music.

Day 7


A day to explore the characterful shops and cafes of Stowe, or hire a bike and cycle the lovely  Stowe Recreation Path. Or take a trip to tour the Ben & Jerry’s Ice Cream factory nearby. There are masses of hiking trails in the area, so you can really experience rural New England at close quarters – beautiful forests, rolling hills and pretty villages with quaint churches.

Day 8

Vermont - The Berkshires (195 miles)

This morning head south out of Vermont and into The Berkshires - a rural region in the mountains of western Massachusetts dotted with pretty villages and towns. This area is well  known for outdoor activities and  farm-to-table food scene. A lovely place to stay over for a night or two to break the journey time to Cape Cod.

Day 9

Cape Cod

Now you’re on the final leg of your New England tour, driving to the peninsula of Cape Cod. The area is rightly popular in the summer, but out of season in the spring and autumn it is more peaceful and you have more space explore the white sand beaches and lovely resorts.

Day 10

Cape Cod

Either enjoy the beautiful white sand beaches on your doorstep or take a day drip to the island of Martha’s Vineyard or Nantucket. You could take a whale watching cruise or visit colourful, artistic Provincetown. There’s masses to do around here, so if you have a few more days to spare, then perhaps extend your holiday.

Day 11

Cape Cod to Boston Airport (70 miles)

After a relaxed start drive to Boston for your flight home.


  • International flights
  • Car hire with fully inclusive insurance
  • Hotels on a Room Only basis as described above (or similar)
  • Electronic roadbook

Recommended Hotels

Here are our hotel suggestions for this self-drive itinerary:

Mid Coast Maine

Classic - Nonantum Hotel & Resort, Kennebunkport

Family - Nonantum Hotel & Resort, Kennebunkport

Deluxe - Portland Harbor Hotel

Character - Kennebunkport Inn

White Mountains, New Hampshire

Classic - White Mountain Hotel & Resort

Family - White Mountain Hotel & Resort

Deluxe - Omni Mount Washington

Character - Merrill Farm Inn


Classic - Golden Eagle Resort, Stowe

Family - Trapp Family Lodge, Stowe

Deluxe - Stowe Mountain Lodge

Character - Trapp Family Lodge, Stowe

The Berkshires, Massachusetts

Classic - The Red Lion Inn Stockbridge

Family - Cranwell Spa & Golf Resort, Lennox

Deluxe- Cranwell Spa & Golf Resort, Lennox

Character - The Red Lion Inn Stockbridge

Cape Cod

Family - Cape Codder Resort

Character - Inn on the Square

Nonantum Hotel and Resort


Established in 1883, this enchanting Kennebunkport resort features elegantly appointed rooms, private baths, fine dining, heated pool, hot tub, recreational activities and service reminiscent of days gone by

White Mountain Hotel and Resort

North Conway

Tucked within the White Mountains on a gorgeous 254-acre estate, this spa resort is only minutes from historic North Conway Village and all the attractions it has to offer whilst offering plenty on onsite facilities to keep you occupied.

Golden Eagle Resort


Ideally located just on the outskirts of Stowe Village, Golden Eagle Resort is in walking distance to shops, restaurants and the Stowe Recreation Path. With a choice of bedrooms and suites, indoor & outdoor pools and lots of activities around the hotel, this is an excellent choice for both couples & families

Kevin Ryan
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