Best of New England Road Trip  

You’re in the driving seat

Go sightseeing in Boston, then hit the road on an unforgettable journey

Driving through New England is spellbindingly beautiful. See wind-beaten coastlines peppered with sailing boats, dotted with lighthouses, and swathed in dunes. Visit cities with history and heritage proudly displayed in architecture, museums, and monuments. And explore rugged wilderness so enchanting it inspired great writers like Emerson and Thoreau.

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Boston, White Mountains, Portland, Cape Cod

Ideal for
Taking your time to explore the beauty of New England.

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Best of New England Road Trip

From £2,575 per person

  • tick10 nights
  • tickBoard Basis - Room Only
  • tickFly with Virgin Atlantic from London Heathrow
  • tick3-4* accommodation for 3 nights Boston
  • tick2 nights White Mountains - NH
  • tick2 nights Portland - ME
  • tick3 nights Cape Cod - MA
  • tick7 days intermediate car rental
  • tickBased on selected October 2024 departures

Recommended itinerary


Fly to the East Coast

Boston's key sights are an obvious draw for those keen to know the USA’s history better. But you’ll also encounter an impressive foodie scene, friendly culture, and the chance to experience the atmosphere when the Red Sox play a home game.

What to do in Boston

Take a tour

The best way to get to know Boston is on foot. Following the well-marked Freedom Trail helps understand Boston’s place in history, but a food tour of North End reveals the neighbourhood’s Italian connections. You can find the time to do both on a day-long tour.

USS Constitution

Where to stay in Boston

Outstanding hotels

For a real sense of place, experience an arty take on Boston’s history at The Revolution in the SoWa area. However, if you fancy somewhere more classically elegant, look no further than Fairmont Copley Plaza.

White Mountains

Pick up your car

From Boston, your road trip begins. You’ll head north on a 150-mile journey into the White Mountains National Forest. While the White Mountains are dusted white in the winter, they're richly green in the spring and summer, and in autumn, they wear a blanket of dazzlingly fiery hues. There's no bad season to experience this heavenly enclave of New Hampshire – each brings its own roster of happenings, whether you're up for an active challenge or simply want the sights to come to you on gentle scenic drives or train rides.

What to do in the White Mountains

Explore outside

The scenery is beautiful in these parts. You’ll want to drive the Kancamagus Scenic Byway, a nature-hugged highway that weaves through the White Mountain National Forest, where falls, gorges, and mountain peaks will leave you in awe. You could also take the Mount Washington Cog Railway to the summit of the highest peak in the northeastern USA.

Where to stay in the White Mountains

A room at the inn?

Stay in a quintessential New England Inn – something like the Bretton Arms Inn will do nicely – it’s an oversized version with plenty of facilities. Otherwise, North Conway is another lovely small town with shops, bakeries, and plenty of outfitters to help you get outdoors.

Portland, Maine


Drive 65 miles southeast to the coastal city of Portland, set on a three-mile peninsula. Portland’s heyday could have been and gone back when its Old Port bustled with activity and ships (guided safely in by its iconic lighthouses) unloaded their cargo into the redbrick warehouses. But happily, it’s a place that’s kept pace with the world, with a burgeoning cultural scene that attracts a curious crowd – impressive for a city of comparatively diminutive proportions.

What to do in Portland

Wander through time

Spend your days strolling and spotting remnants from Portland’s past, whether the 18th-century architecture in the Old Port or grand old Victorian buildings in the elegant West End. Outdoor activities are always on the agenda here, but the city is equally proud of its excellent food served in world-class restaurants, street food vans, and lobster shacks.

Where to stay in Portland

A room with a view

Make the most of Portland’s waterfront location and stay somewhere with a beautiful ocean view. Hyatt Place Portland Old Port is in the city’s historic neighbourhood.

Cape Cod

A sun-splashed finale

The longest leg of your road trip is the 200-mile journey from the White Mountains to Cape Cod. Cape Cod epitomises the classic American seaside and has a storybook landscape of white-steepled churches and historical towns hemmed by sandy beaches and crisscrossed by smooth biking trails. Perhaps it’s no wonder that urban families make a beeline here come summer, searching out Cape Cod’s Americana charm and outdoorsy lifestyle.

What to do in Cape Cod

Lobsters and lighthouses

Provincetown’s main artery is chock full of colourful shops, art galleries, flower-filled gardens, and historic buildings. The water will beckon – perhaps you’ll take a ferry to glorious Martha’s Vineyard or nautically-minded Nantucket for a memorable day trip?

Where to stay in Cape Cod

Beach adventures

Finish your road trip with a beach break on Cape Cod’s sands. If you’re visiting as a family, the Cape Codder Resort has plenty to entertain little ones after days out exploring Cape Cod's towns, beaches, and restaurants.