Best of New England Fly Drive Holiday Itinerary
Arrive at Logan International Airport. Pick up your rental car and proceed to your hotel. Enjoy your evening at leisure, exploring the city.
Boston is the largest city in New England and one of the oldest in the United States, founded by Puritan colonists in 1630. Steeped with history from the American Revolution, here you can explore any portion of the 4 km (2.5 miles) Freedom Trail which starts at Boston Common and passes 16 of the city’s historic landmarks including: Faneuil Hall (a vibrant marketplace),
Paul Revere’s home (from which he made his famous “midnight ride”), the Old North Church, and the USS Constitution (“Old Ironsides”) in Boston Harbor, the oldest warship of the U.S. Navy. Visit the home of the patriots who claimed this city in the name of freedom fighters.
DAY 03: DRIVING DISTANCE: 90 MI / 150 KM
BOSTON – SALEM – PORTSMOUTH – KENNEBUNKPORT
Along the route north of Boston lies almost four centuries of history, as well as some of the coast’s finest beaches and seascapes. First stop is Salem, the location of the infamous witch trials. Then drive 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 04: DRIVING DISTANCE: 210 MI / 340 KM
KENNEBUNKPORT – WISCASSET – BAR HARBOR
Travel along the beautiful Maine Coast to Bar Harbor. Along the way you will pass through quaint fishing villages where fisherman mark their grounds with colourful buoys. Don’t miss the chance to try a lobster or cup of clam chowder.
BAR HARBOR – ACADIA NATIONAL PARK – BAR HARBOR
A full day to explore one of the oldest and most beautiful national parks in America. Discover 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 (466 meters), the highest point on the U.S. Atlantic seaboard.
DAY 06: DRIVING DISTANCE: 230 MI / 370 KM
BAR HARBOR – WHITE MOUNTAINS
Your drive today takes you inland towards the spectacular scenery of the White Mountains, the “rooftop of New England,” a landscape dotted with historic villages and enchanting covered bridges. En-route, experience breathtaking views of mountain ranges and pristine forests.
DAY 07: DRIVING DISTANCE: 120 MI / 200 KM
WHITE MOUNTAINS – VERMONT’S NORTHEAST KINGDOM – STOWE
Today, traverse the White Mountains that divide the New England states of New Hampshire and 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 Stowe.
DAY 08: DRIVING DISTANCE: 160 MI / 260 KM
STOWE – GREEN MOUNTAINS – THE BERKSHIRES
Continue south along Route 100, where you will take in some of the most spectacular scenery in Vermont’s Green Mountains. With their dense forests, the mountains are home to bears, moose, wild turkey, and deer. See picture-perfect villages and some of Vermont’s famous covered bridges before crossing into Massachusetts’ Berkshires, known for their rural beauty and cultural assets. Overnight in the college town of Williamstown.
DAY 09: DRIVING DISTANCE: 180 MI / 290 KM
THE BERKSHIRES – LENOX – NEWPORT
Drive south and pass through a series of wonderful little towns, including Lenox, summer home for the Boston Symphony Orchestra. See Hancock Shaker Village near Pittsfield before continuing to the storied little city of Newport, Rhode Island, once a prosperous colonial seaport.
DAY 10: DRIVING DISTANCE: 100 MI / 160 KM
NEWPORT – CAPE COD
America’s most prominent families – from the Astors to the Vanderbilts – have summered in Newport. Some of their spectacular vacation homes are open for viewing. After sightseeing, continue along the coast on your way to Cape Cod.
A full day 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 vacation spot for visitors and natives alike. Stop in Plymouth, a living panorama of Pilgrim and Colonial times and see the Mayflower II .
DAY 12: DRIVING DISTANCE: 80 MI / 130 KM
CAPE COD – BOSTON DEPARTURE
Today, leave Cape Cod and drive back to Boston. Return your car at the airport before your departure flight.