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Best of New England Road Trip
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.
Itinerary overview
Boston
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’...
White Mountains
The great outdoors
From Boston, your road trip begins. You’ll head north on a 150-mile journey into the White Mounta...
Portland, Maine
Coast-bound
Drive 65 miles southeast to the coastal city of Portland, set on a three-mile peninsula. Portland...
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. C...
Boston
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. 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.
White Mountains
The great outdoors
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. 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.
Portland, Maine
Coast-bound
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. 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.
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. 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?
Other Itineraries
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