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Nantucket, Massachusetts, New England, USA

Self-Drive Journey in New England



12 Days

Prices Start from

£4,600pp (ex. flights)

Suitable for

Couples Adventure Traveller Solo Traveller Photographers Families

Explore the quaint countryside towns, coastal beauty and US revolutionary history of New England, discovering its variety of stunning scenery from white sand beaches to granite coastlines.

Key Highlights of this Itinerary

Bridge in Vermont, New England, USA 1

Drive New England

Hit the road to travel through the rolling colourful expanses of New Hampshire and Vermont.

Harbour, Boston, Massachusetts, New England, USA 2

Live Coastal Life

Visit authentic coastal towns and sample traditional local dishes while sipping sundowners.

Humpback Whale, New England, USA 3

Search for Marine Life

Scan the marine-life-rich waters from the coast or a sailboat for signs of seals, whales and sharks.

Classic Houses on the Water, Nantucket, New England, USA 4

On To Nantucket

Travel to quaint Nantucket, the tiny and isolated island off of Cape Cod.

Why we like it

This scenic self-drive journey through New England takes in the historic city of Boston, the small coastal town of Kennebunkport and the lush inland White Mountain National Forest. The route unveils vast expanses of colourful rolling hills, historic wooden bridges and quaint villages, and routes to the Gilded Age mansions of the elite nautical town of Newport. With just enough time to indulge in a traditional clam bake, relax on white sandy beaches and discover marine wildlife, this in-depth exploration moves through the classic landscapes of New England and changes with the seasons.

Explore our suggested itinerary

  • Days 1-2
  • Day 3
    Boston - Kennebunkport
  • Day 4
    Kennebunkport - White Mountain National Forest
  • Day 5
    White Mountain National Forest
  • Day 6
    White Mountain National Forest - Woodstock
  • Day 7
  • Day 8
    Woodstock - Newport
  • Day 9
  • Day 10
    Newport - Chatham
  • Day 11
  • Day 12
    Chatham - Boston

Now for the details

Acorn Street, Boston, New England, USA
Acorn Street, Boston, New England, USA
Boston, Massachusetts, New England, USA
Boston, Massachusetts, New England, USA

Walk the Freedom Trail

Take a walk on the Freedom Trail to experience what life might have been like during the American Revolution, visiting monuments such as the Paul Reveres House and the former Patriots meeting place of Faneuil Hall. Boston locals are amongst the most passionate and animated sports fans in the country, so a trip to the area would be incomplete without attending a game. The local baseball team, the Boston Red Sox, still play in their original stadium that first opened in 1912. Visit the prestigious Harvard University and learn about its role in the American Revolution and visit the homes of early American literary greats.

Acadia National Park, Maine, New England, USA
Acadia National Park, Maine, New England, USA
Autumn in New England, USA
Autumn in New England, USA

Acadia & Kennebunkport

On the approach to Kennebunkport, pass by old Captain’s houses, artisan galleries, fishing ports and lobster shacks where you can sample the state’s chowders and fried clams. Embark on stunning coastal drives or hop aboard a local boat to explore the seacoast from the water. The neighbouring fishing village of Cape Porpoise is a classic example of a traditional Maine township, and from here visitors can take in stunning views of Goat Island Lighthouse or visit Goose Rocks Beach, one of the country’s most remarkable beaches. A three-hour drive away, but well worth the detour, you might like to visit the stunning Acadia National Park.

Railway Track, White Mountains Nat Park, New Hampshire, New England, USA
Railway Track, White Mountains Nat Park, New Hampshire, New England, USA
Cog Railway to Mount Washington, White Mountains, New England, USA
Cog Railway to Mount Washington, White Mountains, New England, USA

Train Ride to Mount Washington

Visitors to the National Park can hike a small segment of the world-renowned Appalachian National Scenic Trail to catch a glimpse of the surrounding lofty alpine mountaintops and hardwood forests, stopping along the way to admire the clear mountain lakes and streams. We highly recommend the three-hour round trip train ride to the summit of Mount Washington, as well as zip-lining over the eroding hillsides and tubing on the Saco River.

Newport, Rhode Island, New England, USA
Newport, Rhode Island, New England, USA
Lighthouse, Newport, Rhode Island, New England, USA
Lighthouse, Newport, Rhode Island, New England, USA

Cookies in Woodstock & Strolling in Newport

Year-round staples of a jaunt to Woodstock include sampling local craft beers next to an outdoor firepit, browsing for local artwork at one of the galleries, tucking in to warm fresh baked cookies from the bakery or ambling around the farmers’ market. In the lively city of Newport, balance an abundance of high-quality seafood restaurants with strolls past opulent seafront mansions. Known for its variety of art, culinary and music festivals, including the Newport Folk Festival and Newport Jazz Festival, the city is a cultural hot spot and one of the nation’s best kept secrets.

Beach at Sunset, New England, USA
Beach at Sunset, New England, USA
Portland Head Lighthouse in Winter, New Enland, USA
Portland Head Lighthouse in Winter, New Enland, USA

Where All Paths Lead to the Ocean

Renowned for its miles of pristine white sand beaches, Chatham offers countless opportunities for water sports like boating, kayaking and paddle boarding. From the overlook at Chatham Fish Pier, watch as pods of seals follow the fishing fleet in hopes of seizing some of the daily catch. The town features a number of boutique shops and fresh seafood restaurants, the latter of which entice patrons from far and wide, as well as a number of pretty lighthouses and stunning mansions. In a town where almost every street leads to the ocean, Chatham is truly a breath of fresh air.


Below you can see some of the wonderful places we recommend you stay on your journey.

Fairmont Copley Plaza £££££

  • USA
  • City

This centrally located landmark hotel has been a mainstay in Boston’s history since 1912 and offers 383 beautifully decorated rooms and suites set over its five floors. Ideally located in Back Bay, sights such at Beacon Hill, the Boston Public Library and the Freedom Trail are all just a few minutes walk away. The OAK Long Bar & Kitchen provides a farm to table experience using locally sourced ingredients and there is also a rooftop health club.

View Property

Chatham Bars Inn £££££

  • USA
  • Beach and Island Escapes

Originally a private lodge from the early 20th century, the Chatham Bars Inn has been reworked as a luxury boutique hotel. Just a short walk from the town centre, the property is located on a white-sand beach in south-east Cape Cod and features 217 individually decorated rooms and suites, a wellness spa and a range of dining options.

View Property

The Vanderbilt £££££

  • USA
  • Beach and Island Escapes
  • Boutique

Located in the heart of Newport, this vintage mansion built by the Vanderbilt family in 1909 has been newly restored and converted to a luxury boutique hotel. Just a ten-minute drive from other prominent Newport mansions and a short walk from the waterfront America’s Cup Avenue, the location is ideal. Tucked away from the main streets, the property offers a quiet oasis with garden terraces and a roof-top bar that overlooks the harbour. The Vanderbilt has just 33 rooms and suites with a light, chic decor.

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Omni Mount Washington Resort £££££

  • USA
  • Wilderness
  • Wellness and Spa

The Omni Mount Washington Resort is a beautifully restored hotel set inside a historic building in the small town of Bretton Woods at the foot of Mount Washington in New Hampshire. This 200-room resort, built over 100 years ago, features a traditional interior design style and offers stunning views of the White Mountain National Forest. The resort’s sought-after alpine location offers guests the opportunity to embark on a number of outdoor activities from hiking Mount Washington to ziplining, golfing and mountain biking.

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Woodstock Inn & Resort £££££

  • USA
  • Boutique
  • Wellness and Spa

Based in the Green Mountains of Vermont, the Woodstock Inn & Resort is a historical building set in the heart of the pre-revolutionary town of Woodstock. The property features 142 rooms and suites adorned with wood-beam bed frames and luxurious linens. The town of Woodstock is a post-card worthy destination, adorned with historical buildings, a quintessential wood covered bridge and outstanding autumnal foliage. The property offers modern amenities including a spa, golf course and fitness facilities while maintaining its traditional values through handmade furnishing by local artisans.

View Property

Let’s chat

Speak to our experts

Our team is waiting to help you tailor a trip that will leave you with stories for a lifetime. Call us on

01285 601 784

Send us an enquiry

Complete our enquiry form and start your next journey.


All the way through the process - from us explaining what we wanted through to the programme that Roxy created - everything was excellent. Roxy understood our requirements perfectly and created a trip that exactly fitted the bill.

Destination: USA
Travel Expert: Roxy

From my first conversation with Roxy, it was clear that her knowledge was very good indeed. She listened to our ideas and created a fantastic bespoke holiday for us, and the pre-trip information was first class.

Destination: USA
Travel Expert: Roxy

A note on price

Prices will vary depending on the time of year you are travelling. Prices do not include international flights. Please ask one of our Travel Experts for an accurate quote. Flights purchased through Steppes Travel departing from the UK are ATOL protected.

This Itinerary
From £4,600 Per person

When to travel

USA in July

Being one of the hottest months of the year, with temperatures regularly reaching 28°C in the big cities, July remains a peak time to visit the US.

Holiday Inspiration

Our experts have created and curated these tailor-made holiday ideas to get you started. Take the time to search through them and find something that is the spark for your unique adventure.

Why Choose Steppes?

Our knowledge and expertise sets us apart. So too our curiosity. A curiosity of the world and of you, and your passions. It is this that drives us to create a journey that is really bespoke to you, all the while ensuring we travel and operate sustainably.

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