Best of New England - 12 Day Self Drive with flights


Boston | Kennebunkport | Bar Harbor | White Mountains | Stowe | The Berkshires | Newport | Cape Cod

This unforgettable New England self-drive adventure begins in Boston, where you can immerse yourself in the city's rich history and magnificent architecture. Visit the charming coastal towns of Kennebunkport and Bar Harbor, offering stunning beaches, delicious seafood, and picturesque views. Take a scenic drive through New Hampshire's White Mountains and explore the quaint villages of Stowe, Vermont, which are famous for skiing and hiking.

Explore cultural landmarks such as the Norman Rockwell Museum and Tanglewood Music Centre in the Berkshires of Western Massachusetts. Tour opulent mansions from the Gilded Age in Newport, Rhode Island, and enjoy a leisurely stroll along the cliff walk. Finally, explore the idyllic coastlines and charming villages of Cape Cod before concluding your adventure.

This Holiday Includes

  • Flights Return flights from the UK
  • Car Hire 12 Days Car Hire
  • Hotels 11 Nights Accommodation
  • Days 12 Days


Full Itinerary

  • Day 1

    Arrive Boston, Massachusetts

    Hotel: Boston Park Plaza Hotel 4*

    Upon arriving at Logan International Airport, retrieve your rental car and make your way to your hotel. With the rest of the evening at your leisure, take the opportunity to explore the city and enjoy its many attractions.

    Boston, founded in 1630 by Puritan colonists, is not only the largest city in New England but also one of the oldest in the United States. Its rich history from the American Revolution is a major draw for visitors. A must-see attraction is the 2.5 miles Freedom Trail, which starts at Boston Common and leads you on a journey through 16 historic landmarks. These include Faneuil Hall, a bustling marketplace, Paul Revere's home, where he famously embarked on his ‘midnight ride,’ the Old North Church, and the USS Constitution (affectionately known as "Old Ironsides"), the oldest warship in the U.S. Navy, anchored in Boston Harbour. It's an opportunity to explore the homes of the patriots who fought for freedom in this city.

  • Day 3

    Kennebunkport, Maine - 84 Miles

    Hotel: The Nonantum Resort 3*

    Travelling north from Boston you’ll witness almost four centuries of history, along with some of the finest beaches and seascapes along the coast. Begin your journey with a visit to Salem, known for the infamous witch trials. As you continue along the coast, take in the charming harbour towns of Gloucester and Rockport. Experience the old-time seaport ambiance of Portsmouth, New Hampshire, with its abundance of historic buildings before crossing into Maine. Your final stop for the day is the popular resort of Kennebunkport, a haven for writers and artists.

  • Day 4

    Bar Harbor, Maine - 180 Miles

    Hotel: Best Western Acadia Park Inn 3*

    Embark on a scenic drive along the stunning Maine Coast towards Bar Harbor, making your way through charming fishing villages where colourful buoys mark the fishermen's grounds. Don't miss out on the opportunity to savour a delicious lobster or cup of clam chowder while enjoying the beautiful views.

    The following day, you have a full day to discover one of the most ancient and stunning national parks in America, Acadia National Park. Marvel at the soaring peaks, dramatic valleys, crystal-clear lakes, and the rugged shoreline featuring the only true fjord on the U.S. Atlantic coast. You can witness these natural wonders by driving along Park Loop Road or journeying to the summit of Cadillac Mountain, which stands at a height of 1,530 feet (466 meters) and is the highest point on the U.S. Atlantic seaboard.

  • Day 6

    White Mountains, New Hampshire - 193 Miles

    Hotel: North Conway Grand 3*

    Today's journey will lead you inland towards the magnificent scenery of the White Mountains, also known as the ‘rooftop of New England.’ This stunning landscape is adorned with historic villages and charming covered bridges. Along the way, you will be treated to views of mountain ranges and unspoiled forests.

  • Day 7

    Stowe, Vermont - 120 Miles

    Hotel: Trapp Family Lodge 4*

    Today's itinerary involves traversing the White Mountains, which act as a natural divider between the New England states of New Hampshire and Vermont. As you journey through this area, you'll be surrounded by some of the most stunning scenery in New England. You'll pass by Lyndonville and see the iconic Willey's General Store in Greensboro before continuing through the quaint village of Craftsbury, which exudes a charming Grandma Moses vibe, and eventually reaching Stowe.

  • Day 8

    The Berkshires, Massachusetts - 179 Miles

    Hotel: Hilton Garden Inn Lenox Pittsfield 3*

    As you head south along Route 100, prepare to be mesmerized by the stunning views of Vermont's Green Mountains, which are home to an abundance of wildlife such as bears, moose, wild turkey, and deer. Along the way, you'll pass through picturesque villages and admire some of Vermont's famous covered bridges before crossing over into Massachusetts' Berkshires, renowned for their scenic countryside and cultural offerings. Your overnight stay will be in the charming college town of Williamstown.

  • Day 9

    Newport, Rhode Island - 162 Miles

    Hotel: Sonesta Select Newport Middletown 3*

    Traveling southward today will take you through a delightful sequence of charming towns, such as Lenox, which is frequented by the Boston Symphony Orchestra during the summer season. Prior to reaching Newport, Rhode Island, an illustrious historic seaport town, make sure to visit Hancock Shaker Village near Pittsfield.

  • Day 10

    Cape Cod, Massachusetts - 65 Miles

    Hotel: DoubleTree by Hilton Hotel Cape Cod - Hyannis 3*

    Newport has been a summer destination for America's most distinguished families, including the Astors and Vanderbilts. You can even visit some of their remarkable vacation homes. Once you've finished sightseeing, follow the coastline as you make your way to Cape Cod.

    Take an entire day to discover the beauty of Cape Cod, which boasts towering cliffs, undulating dunes, expansive beaches, numerous hiking trails, charming villages, and delectable seafood. As a cherished holiday destination for both tourists and locals, this peninsula promises an unforgettable experience. While you're there, make a stop in Plymouth to witness a living re-enactment of the Pilgrim and Colonial eras and visit the Mayflower II.

  • Day 12

    Depart Cape Cod, Massachusetts's

    Today, your New England journey comes to an end, depart from Cape Cod, and drive back to Boston. Return your car at the airport before catching your departing flight.

View full itinerary

Tailor your holiday

All of our self drive holidays can be tailored to suit your needs; add extra nights and destinations, upgrade your hotels, flights and car hire, or allow us to completely tailor an itinerary that's right for you!

Call today on 0207 749 9282 or enquire online to speak to a member of our expert team. We'll help you bring the art of escape to your American adventure.

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Guide Price: £2,259

Call today on 0207 749 9282 to speak to a member of our expert team.
We'll help you bring the art of escape to your American adventure.

Prices are per person, based on two people sharing a double or twin room and include flights from the UK, pre-booked accommodation, car hire with unlimited mileage. Note: Hotels specified are subject to availability and may be substituted by one of a similar standard. Prices based on travel in low season (November & December 2024). For travel outside of these dates, the itinerary and inclusions may vary to that shown above - please contact us for details.

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