• Explore the red-brick buildings and monuments of Boston
  • Hike, bike, or relax in the mountains of New Hampshire, Vermont and Massachusetts
  • Visit Newport, the summer retreat of America's first millionaires
  • Taste freshly-caught lobster in picturesque Cape Cod and along the dramatic Maine coastline
  • Stay in boutique, characterful hotels and inns

Breathtaking in autumn, picture-perfect in spring and beautiful in summer, New England is one of our favourite destinations for a scenic self-drive holiday. From Boston to Cape Cod, this luxury holiday sees you calling into quaint villages, historic sites and charming boutique hotels as you explore some of the region's prettiest roadways. Go whale-watching in Maine, visit the vast Acadia National Park, and hike among waterfalls in the White Mountains of New Hampshire. See the homes of millionaires along the water at Newport, Rhode Island, and sample fresher-than-fresh seafood in Cape Cod. It's all explored at your own pace, with plenty of time to enjoy the great outdoors and some warm New England hospitality.

Days 1 – 2

UK to Boston

Relax at the airport with included lounge access before your flight to Boston. On arrival, you'll check into your city-centre hotel, just around the corner from the manicured parklands of Boston Common. Before retiring to your room, perhaps dine at the hotel, where signature restaurant 'Mooo....' offers a classic steakhouse menu by award-winning Chef Jamie Mammano. Over the next two days, immerse yourself in Boston's red brick-lined, cobblestone streets. Explore the leafy Harvard campus, the winding lines of Beacon Hill and the world-famous Fenway Park. Delve into the city's history with a visit to the Bunker Hill Monument, the State House or the USS Constitution – the oldest commissioned warship in the world. Then, finish your sightseeing off with a drink at the bar from Cheers

Stay: XV Beacon Hotel (Deluxe)

Acorn Street, Boston

Acorn Street, Boston

Skyline of Boston at sunset

Boston skyline

Day 3

Kennebunkport, Maine

Today you'll collect your hire car and drive north along the cragged New Hampshire coast to Maine. Perhaps pause to explore the 17th and 18th-century houses and quaint riverside gardens of Portsmouth before continuing on to the charming coastal town of Kennebunkport. Commonly known as the summer home of former president George H. W. Bush, it's one of Maine's prettiest seaside towns, dotted with grand mansions and home to the postcard-perfect 1833 Goat Island Lighthouse. Feel the sand beneath your toes on Goose Rocks Beach or Arundel Beach, discover a huge collection of classic streetcars at the Seashore Trolley Museum and shop for souvenirs in the boutiques at Dock Square. You can even take a boat trip out to spot whales, or try your hand at lobster fishing with the locals.

Stay: White Barn Inn (Superior)



Days 4 – 5

Camden, Maine

This morning you'll continue on to Camden, on the Penobscot Bay. This picturesque part of mid-coast Maine offers pristine beaches for swimming and a wealth of beautiful hiking trails in the adjacent Camden Hills State Park – ascend the slopes for views across Camden Harbour and the bay. You'll easily spot Curtis Island, which houses another classic New England lighthouse, just outside the harbour. Depending on when you visit, Camden hosts plenty of fascinating festivals – the US Toboggan Championships, the Windjammer Weekend and the Summer HarborArts Arts & Craft Show to name a few. Don't miss the chance to sample the local seafood; you're well-placed to enjoy coastal fishing trips and watch the lobster boats in action. You're also within easy reach of the Acadia National Park – 47,000 acres of lush woodland, soaring granite peaks and rocky coastline.

Stay: 16 Bay View (Superior) 

Bass Harbor Lighthouse at sunset Acadia National Park, Maine USA

Bass Harbor Lighthouse, Maine

Aerial view of Camden, Maine


Days 6 – 7

White Mountains, New Hampshire

Drive inland through dense forests, winding past crystalline rivers and mirrored lakes to the White Mountains of New Hampshire. Explore the White Mountains Trail, a scenic byway that links panoramic viewpoints with caves, gorges and rushing waterfalls, and head to the top of Mount Washington for spectacular views up to the Presidential Mountain Range and the Great Gulf Wilderness. From your elegant hotel, surrounded by forested hills, you'll have all of Mt. Washington's highlights at your fingertips including some of the region's finest hiking and biking trails.

Stay: The Glen House, Mt. Washington (Superior)

White Mountains, New Hampshire

White Mountains, New Hampshire

White Mountain National Forest, New Hampshire

White Mountain National Forest, New Hampshire

Day 8

Green Mountains, Vermont

Today you'll continue through the White Mountains National Forest along the Kancamagus Highway, a former Indian trail among dense woodland renowned for its spectacular Autumn foliage. Pause among the mirrored waters and golden fields of the Lake District before stopping for the night in Woodstock, Vermont. Here, historic buildings surround a quaint central square, known as the Green, and a nearby dairy farm recreates 19th-century farm life. Hiking trails at the Marsh-Billings-Rockefeller National Historical Park reveal a Queen Anne–style mansion among the rolling countryside.

Stay: Woodstock Inn & Resort (Superior)



Days 9 – 10

The Berkshires, Massachusetts

This morning, a stop at Quechee Village is highly recommended – its glacial ravine is like a miniature version of the Grand Canyon. Then, continue on to the Berkshire Hills in Massachusetts, a set of three mountain ranges separated by the valleys of the Housatonic River in the south and the Hoosic River in the north. In charming Lenox nearby, you can take in performances by the likes of the Boston Symphony Orchestra, take a guided horseback ride through the forest, or simply amble through the Farmers’ Market for lunch. Visit the Hancock Shaker village and soak up its 18th-century heritage, or venture out into the wilderness for scenic hikes. Tour the Berkshire Museum or indulge with a spa treatment at the nearby Canyon Ranch.

Stay: Hotel on North, Pittsfield (Superior)

Quechee Gorge

Quechee Gorge

The Berkshires

The Berkshires

Days 11 – 12

Newport, Rhode Island

Today you'll head Southeast to Rhode Island into Newport – widely renowned as the summer retreat of the first millionaires of America. A walk along Ten Mile Drive reveals row upon row of sprawling mansions – some are open to tours – that make the most of the surrounding coastal scenery. Don't miss Rough Point, the vast oceanside estate belonging to heiress Doris Duke. In Newport itself, take in the town's colonial architecture, go for a sunset stroll along the Cliff Walk and have a drink in America's oldest pub before retiring for the night to your hotel atop Historic Hill.

Stay: Hotel Viking (Superior)

Newport, Castle Hill Lighthouse, Rhode Island

Castle Hill Lighthouse, Newport

Days 13 – 14

Cape Cod

Finish your journey in pristine Cape Cod, driving past windswept sandy beaches and tiny seaside villages. During your stay, depending on the season, there's everything from whale watching to walks among the dunes to enjoy, alongside some of the world's best seafood – be sure to sample some freshly-caught lobster. For something a little different, hop on the ferry to Nantucket, a tiny, isolated island of cobblestoned streets lined with restaurants and high-end boutiques. Alternatively, head to Martha’s Vineyard, known for its cliff-lined beaches and gingerbread cottages. Or, simply follow the Cape Cod Rail Trail along a converted railroad bed along the national seashore – it's an idyllic hiking and biking route. Come evening, return to your hotel for spa treatments and more delicious seafood.

Stay: Chatham Bars Inn (Superior)

Colony of seals at Cape Cod

Colony of seals at Cape Cod

Walkway leads to Brant Point lighthouse, a famous beacon on Nantucket Island in Massachusetts

Nantucket Island

Humpback whale calf breaching in Cape Cod, MA

Whale watching in Cape Cod

Days 15 – 16

Return to the UK

Return to Boston airport to drop off your hire car and board your flight to the UK, landing on day 15.

About the itinerary

"This itinerary is amazing in the Fall, but equally beautiful in Spring or Summer. As far as self-drives go, this is one of my favourites, easily tailored to include everything from whale watching in Maine to hiking in Acadia National Park. And, you can't miss the chance to try the seafood in this part of the world – it's unbelievably fresh and delicious."

Katrin Rummer

Destination Specialist

Pricing information

Guide price from £3,445 pp incl. flights

Low Season from: £3,445 pp
High Season from: £5,855 pp


  • Complimentary UK airport lounge access
  • Return flights between the UK and Boston
  • 11 days car hire (Intermediate car), road book & map
  • 13 nights accommodation in a mixture of 4* (Superior) and 5* (Deluxe) hotels