ultimate new england self drive

8-day fly drive holiday

You’re in the driver’s seat on this fiery New England road trip. From Boston, Massachusetts to the states of New England, it is truly endless beauty from start to finish.

Highlights:

Experience a Red Sox game in fabulous Boston.
Awe at the stunning White Mountains in New Hampshire.
Enjoy an array of outdoor adventures in Vermont.
Stroll the beaches and quaint seaside towns of Cape Cod.

Personalize your itinerary

Your Ultimate New England fly drive holiday can be tailored to suit your needs whether it be adding in extra nights, different accommodations or adding in different stops along the way. Let us know what you would like, and we will work around that.

Fly to the East Coast and collect your hire car from Boston International Airport. Upon arrival into Boston, you will quickly realise a city steep in American history with a delicious foodie scene and exciting attractions. Walk the well-trodden Freedom Trail for a journey through Boston’s history. Time it right and experience the atmosphere of a Red Sox baseball game. From lobster rolls to roast beef sandwiches, you won’t struggle to find a place to eat.

The road trip begins with heading North to Portland, Maine along the scenic Route 1 where you can guarantee pretty coastal views and charming towns to stop off. In Portland, you can visit the Old Port District for its historic buildings and cobblestone streets. Dine in one of the many waterfront restaurants – trying a famous Maine lobster roll is a must! You can then venture to Cape Elizabeth to explore the Portland Head Light, one of America’s most famous lighthouses.

Leave Portland and drive west to the White Mountains, New Hampshire via route 302. Snow-drenched mountains in winter, burning autumnal hues in fall and vibrant green in spring and summer, the drive is stunning no matter what time of year. Make a stop in North Conway for tax-free shopping and tasty local eateries. Continue the journey along the Kancamagus Highway to your accommodation. If you’re up for an adventure, hike Mt. Washington, the Northeast’s tallest peak or for a more laid-back style, take the Cog Railway.

Travel from the White Mountains to the enchanting town of Stowe, Vermont, through the Connecticut River Scenic Byway. One for the outdoorsy types, Stowe is nestled in the Green Mountains and offers a vast mix of outdoor adventures. Spend your day at the Trapp Family Lodge Outdoor Centre before unwinding in the town’s serene atmosphere whilst sampling its local brews.

Heading south on your road trip, take a slightly longer drive to the Berkshires, Massachusetts, a melting pot of cultural richness and enchanting landscapes. Get your camera at the ready as you drive along spectacular Route 7. History addicts, visit the Norman Rockwell Museum in Stockbridge and the historic town of Lenox. If timing permits, don’t miss a concert at Tanglewood, the summer home of the Boston Symphony Orchestra.

Depart from the Berkshires and travel towards Cape Cod, Massachusetts. Pristine white beaches, scenic trails and endless whale spotting - Cape Cod is the perfect finale for this incredible road trip. Check out Provincetown, with its thriving arts scene, historic Pilgrim Monument and whale watching expeditions. Keep an exploration in Sandwich on your radar too, where heritage museums and beautiful gardens blossom. Enjoy the best of seafood at a classy restaurant before catching a Cape Cod Baseball game.

After your two-night stay in Cape Cod, make the 2-hour drive back to Boston where you will head to the airport or onto your onward destination.

Experience the best of Boston and New England with this incredible road trip offering a taste of city life and off-the-beaten-track coastal towns all whilst showcasing New England’s breathtaking natural beauty. This is only a model itinerary of what can be an option, let us know your requirements and we will create an itinerary perfect for you.