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Classic New England

Take a classic journey through this tiny, timeless region

Classic New England

14 Nights From €1599 (Per Person)

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United States 3 Fly Drive Holidays

Massachusetts|| Maine|| New Hampshire|| Vermont|| Rhode Island

Photograph of Classic New England

Take a classic journey through this tiny, timeless region

Classic New England

Boston (Massachusetts) - Kennebunkpoort (Maine) - Bar Harbor (Maine) - Arcadia NP(Maine) - White Mountains (New Hampshire) - Green Mountains (Vermont) - Berkshires(Massachusetts)- Newport (Rhode Island) - Cape Cod(Massachusetts) - Boston (Massachusetts)

It’s small and compact – no bigger than the state of Georgia.  And you could almost visit all six states on a great Sunday drive.  Yet, New Englanders have been packing an incredible amount of authentic heritage and culture into their picture perfect villages for nearly 400 years.  Pretty classic New England towns filled with intriguing museums and attractions, quaint restaurants, and timeless antiques punctuate a landscape of meandering scenic byways, hardwood forests and clear, sparkling streams.  By contrast, Boston and Providence are sophisticated seats of culture, and the region is home to America’s most prestigious universities.  Mount Washington and Mount Mansfield, the highest peaks in the northeast, loom majestically over quaint landscapes with church spires and red covered bridges.  We’ve worked hard to enable you to experience the true essence of New England, which banded together as a tightly knit and fiercely independent region in 1649.  Why New England?  John Smith of the Virginia Company named it that in 1620.  

Your tour starts in Boston, the birthplace of American Independence and a quintessential historic city with narrow streets and winding lanes.  The driving route we’ve planned is classically New England, without too many one night stops.  You’ll have time to savor the beautiful Maine coast, the elegant “summer cottages” of the rich and famous in Rhode Island, and the world-famous beaches and towns of Cape Cod.  You’ll soon discover the dramatic contrast between the coastline and the stunning White and Green Mountains.  If you don’t have time to travel in fall when the foliage is ablaze, this tour is very much for all seasons.  The coastlines of New England are great places in summer.  Spring spouts a bevy of blooming flowers and budding trees.  In winter, many areas take on a new appearance, blanketed with winter-wonderland snow.  No matter what time of year you travel, we are supremely confident that this trip will provide you with memories to last a lifetime!


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Classic New England


Day 1: Arrive Boston

Boston is the very seat of American history. Only Virginia is older than the Massachusetts Colony. The first Thanksgiving was celebrated at Plymouth Rock. The first calls for independence rang out from Boston and the first shots of the American Revolution were fired at Lexington and Concord. The two and one half miles of the Freedom Trail in downtown Boston are likely the most historic blocks in the United States. You can see the Old North Church, Paul Revere’s home and Faneuil Hall, the revolutionaries meeting place that is now filled with restaurants and shops. Walk the trail to get the best perspective of this important piece of Americania. 
Day 2: Explore Boston
The list of other most visited places in Boston includes the Boston Common, a public meeting place since 1630, the Boston Museum of Science, Cheers, of television fame, and the Boston Museum of Arts with its world-renowned collection of 450,000 items. The New England Aquarium offers special whale watching trips until October. Also consider visiting the John F. Kennedy Presidential Library or take the City View Trolley Tour to get an overview of all the historic parts of the city.

Day 3: Kennebunkport
There are many options and routes between Boston and Kennebunkport, but for maximum history coupled with scenic beauty, take the route through the Essex Heritage Area.  Along the way, visit the Saugus Ironworks, established in 1646 and the old sailing ports of Gloucester and Marblehead. Salem was the site of the witch trials of 1694 and now also hosts the Peabody Museum, one of the best in the US.  Other locations along the Essex Heritage Area Scenic Byway celebrate the early history of Massachusetts. When you reach the Kennebunks, stop in the National Register Historic District Village, where the walking tour begins at the Brick Store Museum.

Day 4: Bar Harbor
You’ll be lulled by the constant sound of waves crashing on the rugged Maine coast, the timeless backdrop to “Down East.” This region is home to true culture of “May-nuhs;” seafarers, tradesmen, fishermen and shipbuilders who settled the area.  You’ll discover the best of the “Down East” lifestyle, historic villages, and lighthouses as you meander up the Maine Coast. Or, you can take the inland route and arrive in Bar Harbor more quickly. .

Day 5: Bar Harbor/Acadia National Park
Make sure to explore both parts of Acadia National Park: Mount Desert Island and the Schoodic Peninsula. You can take a bus from place to place or do the scenic drives along the coast of both yourself. Three mainland visitor’s centers complement the one on Little Cranberry Island reached only by ferry. You can also explore the serene carriage roads that John D. Rockefeller built for the wealthy out of towners who lived in the area until most of their homes were destroyed by fire.

Day 6: New Hampshire’s White Mountains
On your way between Bar Harbor and the White Mountains, take some time to explore Maine’s Rangeley Lakes region, a Norman Rockwell picture postcard area still hailing from the era when well-to-do “flatlanders,” (as the locals call anyone from south of New Hampshire), arrived to establish “camps,” or elaborate summer houses in the region.  Today, there’s not so much as a stop light to slow you down. Smaller nearby Oquossoc (Native American for “landing place”) is for folks who really like the quiet.

Day 7: Explore the White Mountains Area
Likely the White Mountains will be what you expended in quintessential New England. Cold clear rushing streams reflect the bright green of summer or the blazing colors of the fall that set the hillsides on fire.  Towering granite cliffs and soaring mountains often hug both sides of the road. Discover the history of the White Mountain Trail and beauty of the Kancamagus Highway National Scenic Byway and of course, plan to travel to the summit of Mt. Washington, whether by car, cog railway or guided tour. Many charming villages along the way still look as they did when writer Nathaniel Hawthorne and painter Thomas Cole lived here in the 18th century. The pace of life in many places hasn’t changed much either.

Day 8: Vermont’s Green Mountains
It would be hard not to be on a scenic road as you travel from the White Mountains to the Green Mountains today. Even the Interstate highway between Franconia and St. Johnsbury is a scenic drive. Is you like roads less traveled, delightful routes with names like Smuggler’s Notch and Middlebury Gap are sprinkled all over Vermont. Montpelier had only 113 residents when it was designated Vermont’s capital,  due to its central location. It is still the smallest capital city in the nation. 

Day 9: Green Mountains
The lush foliage, white steepled churches, winding roads, and quaint New England towns of the Green Mountains can feel as old as time  Much of the countryside hasn’t changed a great deal since the Green Mountain Boys declared Vermont its own country 230 years ago. Nearly 75 years have passed since the von Trapp family settled in Stowe.  The “hills are still alive with the sound of music.” Mountains here have interesting names like Camels Hump and Crouching Lion.  Divided sharply into east and west sections by the lofty hills, early settlers chose their representatives to balance the government from both sides, a phenomenon now known as “mountain rule.” New England independence at its finest!

Day 10: The Berkshires
Traveling south to Massachusetts, you’ll find the Berkshires home to Normal Rockwell picture perfect scenery. The Sterling and Francine Clark Art Institute in Williamstown has an outstanding collection of French Impressionist paintings while the beautifully restored Hancock Shaker Village is the premier collection of Shaker buildings.  Artifacts, furniture, craft and household items are exhibited in 20 historic buildings. The Red Lion Inn in Stockbridge still looks like it did in Rockwell’s most famous painting. Make tine to take dinner there, for a true New England experience. 

Day 11: Newport, Rhode Island
You have several options traveling between The Berkshires and Newport. You can experience New England pioneer lifestyle up close and personal at Old Sturbridge Village. Mystic, Connecticut has an authentic 19th century seafaring village of more than 30 England trade shops and businesses moved from around New England. An alternate route through the Blackstone River Valley in Rhode Island takes you through the heritage of America’s first industrial area.  Water-powered spinning mills used new technology that was spirited from England in 1797. Samuel Slater’s original mill where the first new machines were installed has been impressively restored to pristine working condition.

Day 12: Explore Newport
Opulence reigned in Newport during the Gilded Age. Bellevue Avenue was home to the “summer cottages” of the rich and famous from New York and Philadelphia, the same Vanderbilt’s, Astor’s and other prominent families who spent part of their summers on Mt. Desert Island. You can pack your day in Newport as full as you would like. The Breakers and Rosecliff are spectacular mansions. Take the Cliffwalk which follows the coastline and the cliffs. A 10 mile scenic driving tour begins at The Elms. And, there’s great shopping and browsing and a Newport Winery.

Day 13: Cape Cod
Distances are short in New England, so the whole drive to Cape Cod today is only 80 miles. That should leave time to swing through Providence, Rhode Island where Benefit Street is considered to be the best preserved historic mile in America.  Fall River, Massachusetts was known during the Industrial Revolution as the “Textile Capital of the World,” while New Bedford was once the whaling capital of New England.  There should be time to visit all three along the way

Day 14: Explore Cape Cod
The scenic drive on fabulous Cape Cod stretches all the way from the beginning of peninsula to Provincetown at the very end. Beautiful white beaches line the Cape Cod National Seashore. Take a ferry to historic Nantucket or Martha’s Vineyard, or sign up for a whale watching cruise.

Day 15: Cape Cod to Boston
On the way back to Boston today, you can experience frontier New England at Plymouth Plantation, where a living history museum features life in 1627 – just seven years after the colonists landed at Plymouth Rock. 

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