Autumnal road landscapes in New England
Autumnal road landscapes in New England
Boston, Kennebunkport & Portland scenery
Boston, Kennebunkport & Portland scenery
Acadia National Park & The White Mountains in New Hampshire
Acadia 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 €2,449 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 Acadia National Park, and the lovely coastal town of Acadia. 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.


  • Return international flights
  • Fully inclusive car rental – upgrades available at a supplement (eg: SUV or convertible)
  • Hotel accommodation in 3* to 4* hotels  on a room only basis unless otherwise stated
  • Electronic maps & driving instructions

What’s not included

  • Resort fees
  • Parking charges
  • Meals, excursions & entrance fees
  • Fuel & road tolls

Hilton Boston Park Plaza


Located in the heart of historic Back Bay, The Hilton Boston Park Plaza Hotel is one of Boston’s most recognized and renowned landmarks. The hotel is a member of Historic Hotels of America and opened March 10, 1927 as part of the E.M. Statler Empire. In a great location, by the Public Garden & Theatre District.

Kennebunkport Inn


This charming hotel is situated on the south coast of Maine. Perfectly located by Dock Square, in the heart of this seaside village, it is just steps away from historic sights, galleries, and speciality shops.

North Conway Grand

North Conway

Situated adjacent to the Settlers Green Outlets in the Mountain Washington Valley, providing easy access to both summer and winter adventures as well as outstanding shopping.

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

The Red Lion Inn Stockbridge


The Red Lion Inn, located in Stockbridge, Massachusetts, is a historic and iconic hotel that has been welcoming guests since 1773. It is nestled in the charming Berkshires region, offering a picturesque and quintessential New England experience. The inn features colonial-style architecture, antique furnishings, and a warm, welcoming ambiance.

Dan'l Webster Inn

Cape Cod

The Dan'l Webster Inn, established in 1692, is one of the oldest continuously operating inns in the US. Located in Sandwich, Massachusetts, it offers classic New England hospitality with modern amenities. The inn features traditional decor, a renowned restaurant emphasizing regional and seasonal ingredients, and a tranquil setting in the scenic Cape Cod region.

The Lenox Hotel


The Lenox Hotel in Boston is a historic luxury hotel located in the vibrant Back Bay neighbourhood. Since 1900, it has been a symbol of elegance and sophistication in the city. The hotel offers beautifully appointed rooms and suites and fine dining option. Its central location provides easy access to Boston's attractions, shopping, and dining destinations, making it a favourite among travellers seeking a memorable stay in the heart of the city.

The Lodge on the Cove


The Lodge on the Cove in Kennebunkport, Maine, is a charming and contemporary boutique hotel. With its coastal location and modern amenities, The Lodge on the Cove offers a unique and welcoming family-friendly retreat in the picturesque town of Kennebunkport. Guests can enjoy amenities like an outdoor pool, complimentary bikes, and access to Goose Rocks Beach.

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.

Trapp Family Lodge


Situated on 2,500 acres in beautiful Stowe, Vermont, the Trapp Family Lodge is a unique luxury mountain resort featuring Austrian-inspired architecture and European-style rooms.

The Cape Codder Resort


Popular with families, this is a comfortable, traditional hotel with a great choice of amenities, facilities and activities. There is a great indoor wave pool, heated outdoor pool, spa & fitness room, two restaurants and an outdoor courtyard and gardens where you can enjoy movies in the evening.

Fairmont Copley Plaza


Located in historic Back Bay a symbol of Boston’s rich history and elegance recently renovated and restored to shine more brightly than ever before. Rich with heritage, The Fairmont Copley Plaza epitomizes the culture and traditions of Boston.

Portland Harbor Hotel

Portland Maine

The Portland Harbor Hotel is a charming accommodation located in Portland Downtown Old Port. Embracing a coastal theme, each room features sleek wood floors and cozy decor, providing a luxuriously quaint, nautical atmosphere. With its prime location in the heart of Portland, the hotel offers a convenient and delightful base for exploring the city and enjoying its maritime charm.

Omni Mount Washington Resort

White Mountains

A grand, historic resort in Bretton Woods, renowned for its luxurious décor, fine dining and live music, the Omni Mount Washington Resort offers a relaxing and indulgent stay.

The New Lodge at Spruce Peak


The Lodge at Spruce Peak (formerly Stowe Mountain Lodge) is located at the base of Mount Mansfield within Stowe Mountain Resort, this fabulous lodge is perfectly placed for myriad activities throughout the year, and a wonderful choice for all ages.

Katie Guy
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