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New England coast

Discover New England

16-day tailor-made self-drive from £2,575 pp incl. flights


Short description

Showcase the unique heritage and spectacular natural world of each of New England’s six states


  • Immerse yourself in revolutionary and colonial heritage
  • Take in the wild beauty of the White and Green mountains
  • End with the beaches and harbour towns of Cape Cod
  • From coastal sweeps to mountain passes, enjoy scenic drives throughout
  • Stay in curated hotels, including seaside retreats and historic getaways

In Brief

  • 2 Nights Boston
  • 1 Night Kennebunkport
  • 2 Nights Bar Harbor
  • 1 Night White Mountains
  • 1 Night Woodstock
  • 2 Nights Pittsfield
  • 1 Night Mystic
  • 2 Nights Newport
  • 2 Nights Cape Cod


Recommended for:
City | History & culture | Natural world | Self-drive | September holidays

New England is the birthplace of America – something remembered by Boston’s revolutionary sights, the grand manors of the Berkshires and the maritime heritage of Connecticut. But, spanning all six states, this curated road trip showcases so much more. Coastal drives and forest loops will see you between national-park islands, Maine lobster shacks and great forested mountains to end with beach-clad Cape Cod’s whales and fishing villages. It’s all brought together with stays in hand-picked hotels.

Day by day itinerary

Days 1-2

From the comfort of your included VIP airport lounge, you’ll board a day flight to Boston, where you’ll make your way to your hotel. While our Deluxe option is especially inviting for its early-20th-century good looks, both are centrally located, with all of the city’s delights on their doorstep. Wandering the cobblestone streets of the Massachusetts capital will bring you between historic sights that chart the American Revolution, from redbrick churches to timber tall ships. That’s without mentioning the leafy Harvard campus in Cambridge, the boutiques of Newbury Street and the pretty narrow lanes that wind through the townhouses of Beacon Hill.

Stay: Hilton Boston Park Plaza (Standard) Fairmont Copley Plaza (Deluxe)

Day 3

Collecting your hire car, you’ll travel north along the New Hampshire coast, passing cragged bays to arrive into Maine. Then, after perhaps pausing at Portsmouth’s tree-lined streets and 18th-century colonial buildings, you’ll arrive into Kennebunk. As one of Maine’s prettiest seaport villages, it’s a favourite among the East Coast elite – something evident across elegant sea-facing mansions. George HW Bush even has a home here, while its pretty beaches offer further reason to linger. Both of our hotel options here are perched idyllically on the water.

Stay: Nonantum Resort (Standard) or White Barn Inn, Kennebunkport (Superior)

Days 4-5
Bar Harbor

Continuing north, you’ll sweep along the coast to Mount Desert Island. Home to Acadia National Park, it’s a region of sparkling lakes and old-growth forests that form the backdrop to serene hikes and kayak trips. We also highly recommend the drive up to the top of Cadillac Mountain. As one of the highest points on the eastern seaboard, it offers some truly majestic views. Your base for your two nights here is Bar Harbor, where weatherboard houses sit side by side with cute cafés that spill out onto the streets. It’s all fronted by glistening Frenchman Bay – a view showcased by both of our traditional-hotel recommendations.

Stay: Best Western Acadia Park Inn, Bar Harbor (Standard & Superior)

Day 6
White Mountains

Heading inland today, you’ll plunge through forests, dart across rivers and trace lake outlines to arrive into New Hampshire’s White Mountains. Here, hikes and skiing trails make the most of these New-England icons, while scenic drives bring you atop Mt. Washington and along the White Mountains Trail. This scenic byway sees you between cave gorges, scenic overlooks and waterfall-troubled chasms. 

Stay: Christmas Farm Inn, Mt. Washington (Standard) Glen House, Gorham (Superior)

Day 7

Travelling along the Kancamagus Highway – a former Indian trail that cuts through the White Mountains National Forest – you’ll continue on through dense woodland, famed for its autumn foliage. You’ll first arrive at the idyllic Lakes District, its glassy waters and golden fields pointing towards Vermont. Your home for the night will be Woodstock, a pretty village set among rolling countryside. Here, grand houses, churches and an oval green remember its 18th-century roots as the dignified seat of Windsor County.

Stay: 506 on the River (Superior) or Woodstock Inn & Resort (Superior)

Days 8-9
The Berkshires

Today, we highly recommend a visit to next-door Quechee Village to take in its glacial ravine – a Grand Canyon in miniature. It’s then on to Massachusetts and the Berkshire Hills. Long a green lung for New York’s moneyed, there are plenty of opportunities for hikes and stops at farm-to-table restaurants. Hancock Shaker Village is a special highlight for its 18th-century heritage. Your base for it all is Pittsfield nearby the charming Lenox. Often termed the ‘cultural heart of the Berkshires’, Lenox impresses with grand houses and summer performances by the world-class Boston Symphony Orchestra. 

Stay: Hotel on North (Standard & Superior)

Day 10

Heading into Connecticut, you’ll arrive back at the coast with Mystic. From its humble, 17th-century beginnings it grew into one of the greatest shipbuilding ports of the East Coast, churning out clippers, gunboats and naval ships throughout the 1800s. It’s a storied history that lives on to this day in the superb Mystic Seaport Museum. As America’s leading maritime exhibition, it’s a true step back in time, complete with everything from historic villages to working shipyards. You’ll contrast it all with the contemporary sleek of your hotel.

Stay: Whaler's Inn, Mystic (Superior)

Days 11-12

Hopping south into Rhode Island, you’ll arrive into Newport – the summer resort of America’s first millionaires. Be sure to take a stroll along Ten Mile Drive to appreciate its stunning mansions, several of which are open for tours. Rough Point is a special favourite – a spectacular ocean estate of heiress and art collector, Doris Duke. Then, there’s the town’s colonial architecture, the pretty Cliff Walk and what’s believed to be America's oldest pub before you end the night in your cosy accommodation.

Stay: Admiral Fitzroy Inn (Standard) and Hotel Viking (Superior)

Days 13-14
Cape Cod

Your drive along Cape Cod is a true trip highlight, bringing you between sandy beaches and quaint seaside villages. With both of our hotel options found right on the coast, it all makes for ideal, end-of-trip relaxation and some truly superb seafood. Don’t miss out on the just-caught lobster. And, if you can tear yourself away from the dune-backed sands, further highlights range from whale-watching cruises to artsy Provincetown’s colourful charm.

Stay: Hyannis Harbor Hotel (Standard) Chatham Bars Inn (Superior)

Days 15-16

On your return drive to Boston, perhaps stop off at Plymouth where the Pilgrim Fathers first settled in 1620. Then, returning your hire car at the airport, board your overnight flight back to the UK.



Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

Accommodation rating: Standard Superior Deluxe

16-day tailor-made self-drive
from £2,575 pp incl. flights


Low Season

from £2,575 pp. incl. flights

High Season

from £3,860 pp. incl. flights


  • Complimentary UK airport lounge access
  • Return flights between the UK and Boston
  • 13 days Compact car hire including personalised road book
  • 14 nights accommodation in typically 3* (Standard) and 4* (Superior) hotels on a room only basis

High season: June-October

Terms & Conditions

Prices are per person based on two people sharing a twin/double room; prices are subject to availability and possible change; normal booking conditions apply.

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At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0636 to discuss how we can tailor your holiday.

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