Best of New England - Fly Drive

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

Our suggested fly drive itinerary showcases the natural beauty and scenic vistas that only New England conjures. Start in Boston, the gateway to this region, steeped in history that effortlessly blends with modern city life. Then, take in the glorious Maine coastline for unforgettable views of the rugged cliffs and lighthouses that hug this state. Afterwards, drive inland for the breathtaking mountain ranges and scenic beauty of New Hampshire and Vermont. Next, is the lively arts scene of The Berkshires in Massachusetts before visiting Newport, the holiday retreat destination for American royalty. Your holiday finishes up in Cape Cod, the ideal place to unwind and soak up the ocean air and sweeping beaches, with many quaint coastal towns on hand to pick up mementos of your New England discovery.


Highlights

1. Take a walk along the historic Freedom Trail in Boston.
2. Drive along the scenic Route 1, hugging the Maine coastline for New England scenery at its best.
3. Explore the Mayflower II in Cape Cod, a reproduction of the ship that brought settlers to the US in 1620

Day 1: London to Boston

Arrive at Logan International Airport and collect your Alamo rental car before proceeding into Boston, the largest city in New England and one of the oldest in the United States. Your evening is at leisure, so why not head to the lively Back Bay area to discover local fine dining and entertainment options.

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Day 2: Boston

Steeped in history from the American Revolution, the best way to capture many of Boston’s iconic sights is with a walk along the Freedom Trail which starts at Boston Common and passes many of the city’s historic landmarks including the vibrant Faneuil Hall Marketplace, Paul Revere’s home (from which he made his famous ‘midnight ride’) and the USS Constitution (‘Old Ironsides’) in Boston Harbour, the oldest warship of the U.S. Navy. Then there’s the winding cobbled streets of Beacon Hill to explore and Quincy Market, pay a visit to the Boston Tea Party Museum or the John F/ Kennedy Library, and enjoy the city’s multicultural background, with a wander through Little Italy to sample the linguini or maybe taste Peking Duck in Chinatown?

Day 3 : Boston – Salem – Portsmouth – Kennebunkport (approx. 90 miles)

It’s time to hit the open road, as you travel north of Boston where almost four centuries of history lines the coastline, as well as some of the finest port towns and beaches. First stop is Salem, the location of the infamous witch trials. Continue along the coast to the charming harbour towns of Gloucester and Rockport. Enjoy the old-time seaport atmosphere of Portsmouth, New Hampshire and its wealth of historic buildings before crossing into Maine. Your destination today is the popular resort of Kennebunkport, a haven for writers and artists.

Day 4: Kennebunkport – Wiscasset – Bar Harbor (approx. 90 miles) 

After your evening in Kennebunkport, drive further north along the beautiful Maine Coast to Bar Harbor. Along the way you will pass through quaint fishing villages where fishermen mark their grounds with colourful buoys. Don’t miss the chance to try a lobster or cup of clam chowder, a quintessential New England dish. Arrive into Bar Harbor, the ideal base to explore the Acadia National Park. This pretty coastal town is one of Maine’s premier summer resorts and provides ample opportunity to get out on the water or sample the local lobster specialities, breweries or boutique shops dotted around town.

Day 5: Bar Harbor – Acadia National Park – Bar Harbor

Today, you have a full day to explore one of the oldest and most beautiful national parks in America. Discover over 50 square miles of soaring peaks, dramatic glacier-carved valleys, clear lakes, and the rugged shoreline with the only true fjord on the U.S. Atlantic coast. Witness the area’s natural wonders from Park Loop Road or drive to the summit of Cadillac Mountain, at 1,530 feet, the highest point on the U.S. Atlantic seaboard, and will guarantee to offer breathtaking views of the coastline.

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Day 6 - 7: Bar Harbor – White Mountains (approx. 230 miles)

After your outdoor adventure of the Acadia area, your drive today takes you inland to New Hampshire and the spectacular scenery of the White Mountains, a landscape dotted with historic villages and enchanting covered bridges. Your journey will take your through some outstanding landscapes past rugged mountain ranges and verdant green forests to arrive into the ‘rooftop of New England’. From vintage trains, tax free shopping and outdoor pursuits, the White Mountains offers it all. If time allows, take a drive up to the top of the Mount Washington Auto Road, where on a clear day you can look out to Boston and even the Atlantic!

Day 7: White Mountains – Vermont’s Northeast Kingdom – Stowe (approx. 120 miles)

Today, continue your drive through the White Mountains as it spreads through northern New Hampshire and into Vermont. The route takes you through some of New England’s most beautiful scenery. Drive by Lyndonville and see Willey’s General Store in Greensboro before continuing through Craftsbury, a Grandma Moses kind of village, to the ski resort of Stowe. This 200-year-old village is ideally situated between Mt. Mansfield and the peaks of the Green Mountains, making it the ideal mountain escape, so make sure to take a drive up the mountain or by gondola for impressive views over the area. 

Day 8: Stowe – Green Mountains – The Berkshires (approx. 160 miles) :

Continue south past Waterbury, home to the Ben & Jerry’s factory - if time allows, then why not book a tour? Then head for Route 100, one of the national scenic byways where you will take in the spectacular scenery of Vermont’s Green Mountains. With their dense forests, the mountains are home to bears, moose, wild turkey, and deer. Drive past picture-perfect villages, including and some of Vermont’s famous covered bridges before crossing into Massachusetts’ Berkshires, known for their rural beauty and cultural assets. 

Day 9: The Berkshires – Lenox – Newport (approx. 180 miles)

Your New England discovery will now take you from Massachusetts to Rhode Island, as you drive south and pass through a series of wonderful little towns, including Lenox, summer home for the Boston Symphony Orchestra. Be sure to see Hancock Shaker Village near Pittsfield before continuing to the storied little city of Newport, a once a prosperous colonial seaport of Rhode Island. 

Day 10: Newport – Cape Cod (approx. 180 miles) 

Spend time looking around Newport this morning, the holiday playground for where America’s most prominent industrialist families – from the Astors to the Vandebilts – summered back in the heyday of the 19th century. See how America’s royalty lived, with their palatial mansions now open for viewing. Then it’s on to the glorious Massachusetts coast, as you head for your final destination of Cape Cod, sitting pretty along a dramatic coastline shaped by the Atlantic Ocean

Day 11: Cape Cod

Today is completely at your leisure to explore magnificent Cape Cod with its high cliffs, rolling dunes, broad beaches, miles of walking trails, picturesque villages and delicious seafood. This peninsula is a beloved holiday spot for visitors and locals alike. Stop in Plymouth, a living panorama of Pilgrim and Colonial times and see the Mayflower II, or take a drive along the Cape Cod National Seashore, stretching 40 miles into a curl to the tip of Cape Cod’s tail where you can find the quirky and chic town of Provincetown. Perhaps book in a dune tour for a ride through the rolling sands and sweeping beaches, and get your fill of the nautical lighthouses and ocean vistas that surround the area and truly sum up the image of New England.

Day 12: Cape Cod – Boston – London

After your breathtaking journey around the coast, mountains and quaint port towns of New England, it’s time to drive back to Boston, where you will return your rental car at Logan International Airport before your departure flight.

We can tailor this or any tour to match your dream New England holiday so, complete the form or call our team now to discuss.