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Explore Boston’s Seaport on foot and view the Boston Lighthouse which holds a headlight visible for sixteen miles “as a reminder of the inextinguishable American spirit.” To take a closer look, there are several guided harbor tours to get you there. Travel north to the rocky shores of Gloucester and Rockport where you may photograph the iconic red fishing shack: “Motif Number One,” symbolic of New England maritime life.
Continue your trip along mid-Coastal Maine to the picturesque fishing village of Cape Porpoise Harbor and view of the Goat Island Lighthouse. Continue to Portland, Maine’s largest city, originally a colonial seaport. Stroll cobblestone streets, visit eclectic art galleries and perhaps enjoy a bowl of piping hot New England clam “chow-dah” alongside Casco Bay. Enjoy a stroll at peaceful Rockland Harbor and walk along the breakwater path to see Rockland Breakwater Lighthouse.
Next up is Bar Harbor, on Mt. Desert Island, home to Acadia National Park. Dotting the island’s entrance, traditional lobster pounds with huge outdoor boiling cauldrons cook crustaceans to perfection. Locals say that in Acadia National Park you can “catch fish with one hand while picking wild blueberries with the other.”
Drive along the spectacular Bay of Fundy, currently in the running to be one of the earth’s new seven natural wonders. The Bay hosts the highest tides in the world as the 12-hour tidal period can see changes to the height of a five story building. The Bay of Fundy is also home to many species of rare and endangered whales.
The Exciting Parts
- Long Island Gold Coast Mansion Tour
- Experience the summer getaway for New York City elite in the elegant Hamptons
- Leisurely lunch in historic and picturesque Mystic, Connecticut
- Mansion tours of Newport, Rhode Island
- Visit the affluent seaside retreat of Hyannis on Cape Code
- Experience the sights and sounds of historic Boston
*Admission fees not included
Boston - Gloucester - York/Kennebunkport
York/Kennebunkport - Portland - Rockland - Rockport/Camden
Rockport/Camden - Bar Harbor
Bar Harbor - Acadia National Park - Bar Harbor
Bar Harbor - Bay of Fundy - St Andrews, Canada
St Andrews, Canada - Bangor
Bangor - Kittery - Portsmouth
Portsmouth - Cape Cod
Cape Cod - Boston Departure
Day 1 Boston Arrival
Explore Boston's Seaport on foot and view the Boston Lighthouse which holds a head light visible for sixteen miles "as a reminder of the inextinguishable American spirit." To take a closer look, there are several guided harbor tours (optional, fees apply) to get you there. Tonight, enjoy dinner at Boston's world famous waterfront. Weather permitting, may we suggest a harborside evening stroll to see the moonlight dancing on the water.
Day 2 Boston - Gloucester - York/Kennebunkport
Today travel north to the rocky shores of Gloucester, originally settled shortly after Plymouth Colony, and made famous as the movie setting for the blockbuster "The Perfect Storm" starring George Clooney. Take a stroll on Rocky Neck's Historic Art Trail, relive the legends of artists and authors of the 19th and 20th centuries. Next is Rockport where you may photograph the iconic red fishing shack: "Motif Number One," symbolic of New England maritime life. Here, may we suggest a picnic lunch on Long Beach while gazing upon Thacher Island's Twin Lighthouses made famous by artist Winslow Homer, the only surviving multiple lights of the U.S. Coast. After lunch, cross to York where you can see Maine's southernmost light, Cape Neddick Lighthouse, and gaze at Boon Island Lighthouse just offshore. Your destination today is Kennebunkport, summer home for many U.S. Presidents.
Day 3 York/Kennebunkport - Portland - Rockland - Rockport/Camden
Today your journey continues along mid-Coastal Maine. A short drive along Main Street brings you to the picturesque fishing village of Cape Porpoise Harbor and view of the Goat Island Lighthouse. Next, Old Orchard Beach awaits. Although its amusement park and famous pier have drawn visitors for centuries, it is best known for its long stretches of soft golden sand. Here, you may wish to pick up a box of locally made sweet salt-water taffy, dip your toes in the cool Atlantic waters, try your luck at a game of chance or take a walk along the boardwalk. Continue to Portland, Maine's largest city, originally a colonial seaport. Stroll cobblestone streets, visit eclectic art galleries and perhaps enjoy a bowl of piping hot New England clam "chow-dah" alongside Casco Bay. Finish your exploration by visiting the Portland Head Lighthouse. To the north, you'll pass through the town of Thomaston and by the aging penitentiary which inspired for the movie "Shawshank Redemption" starring Morgan Freeman. Your drive continues today to the "Lobster Capital of the World," Rockland, Maine. Here you may view Maine landscape paintings made famous by Andrew Wyeth at the Farnsworth Art Museum (optional, fees apply). Enjoy a stroll at peaceful Rockland Harbor and walk along the breakwater path to see Rockland Breakwater Lighthouse. Just north of Rockland, the towns of Rockport and Camden offer some of the best views in the state.
Day 4 Rockport/Camden - Bar Harbor
Camden, the backdrop for the film "Peyton Place," is a quaint town by the sea. Here, you may wish to take a sightseeing cruise, go kayaking, or take a day sail around Camden Harbor (optional, fees apply) to see Curtis Island Lighthouse. Your destination today is Bar Harbor, on Mt. Desert Island, home to Acadia National Park. Dotting the island's entrance, traditional lobster pounds with huge outdoor boiling cauldrons cook crustaceans to perfection. This evening, may we suggest a stroll along the quaint streets of Bar Harbor, gazing at the small island for which the city was named, Bar Island, accessible by foot, at low tide only, across Frenchman Bay.
Day 5 Bar Harbor - Acadia National Park - Bar Harbor
Explore the oldest national park east of the Mississippi River. Locals say that in Acadia National Park you can "catch fish with one hand while picking wild blueberries with the other." During select periods of the year, Acadia runs a free shuttle service through the park to see the vast attractions without the hassles of parking. Cadillac Mountain, the highest point on the eastern seaboard north of Brazil, is a perfect spot for sunrises, sunsets and star gazing. Also along Park Loop Road, you may stop at Sand Beach. Proximal Thunder Hole is a small inlet carved out of the rocks where waves rush in and clap like thunder. Additionally worth noting is the Jordan Pond House, located on an original carriage trail. This is a favorite spot to enjoy tea and a world renowned Jordan Pond Popover. Time permitting you may wish to explore the Bass Harbor Lighthouse.
Day 6 Bar Harbor - Bay of Fundy - St Andrews, Canada
Today travel to West Quoddy Head where a striking red-and-white striped lighthouse marks the easternmost point in the United States. Drive along the Sunrise Coast, where the first morning light hits the USA and the coastal rim's stunning granite bedrock meets a restless sea. A short drive takes you across the Franklin D. Roosevelt Memorial International Bridge to Canada's Campobello Island, a favorite destination for the U.S.'s 32nd President. Today Campobello Provincial Park holds his expansive residence, estate gardens, walking trails, and provides a refreshing stop. Return to the U.S. for a drive along the spectacular Bay of Fundy, currently in the running to be one of the earth's new seven natural wonders. The Bay hosts the highest tides in the world as the 12-hour tidal period can see changes to the height of a five story building. The Bay of Fundy is also home to many species of rare and endangered whales. Crossing the international border again, you'll reach your final destination: St. Andrews-By-The-Sea, Canada's oldest seaside resort town.
Day 7 St Andrews, Canada - Bangor
Enjoy a leisurely morning in picturesque St. Andrews. You may wish to visit Kingsbrae Horticulture Garden (admission fee applies) or walk along the waterfront. Returning to the international border, you'll pass through the "Chocolate Capital of Canada," St. Stephen. Then, follow "the Airline" to Bangor. The route, formerly the fastest stagecoach trail from the Canadian border, passes through spruce forests and blueberry barrens. This route is one of the most scenic through Maine's inland timberland country. Arriving in Bangor, once the Lumber Capital of the World, a 31-foot-tall statue of lumberjack Paul Bunyan greets you. This afternoon you may visit Cole Land Transportation Museum (optional, fees apply), explore the picturesque 660-acre campus of the University of Maine or walk in the footsteps of novelist and movie writer Stephen King, a long-time Bangor resident, whose Victorian mansion home with wrought iron ghouls graces a nearby neighborhood. This evening you may wish to stroll the banks of the tranquil Kenduskeag.
Day 8 Bangor - Kittery - Portsmouth
Journey south through Maine's capital, Augusta, to Kittery. The area is known for its many shopping outlet stores; and for its seaport. From historic Fort Foster, enjoy a photo stop on the battery's grassy knoll overlooking Whaleback Lighthouse. Continue south to Portsmouth, New Hampshire, the seacoast's economic center rich with maritime history. Tonight you may wish to enjoy a classic seafood favorite in historic downtown on the banks of Portsmouth's Piscataqua River.
Day 9 Portsmouth - Cape Cod
Today, your journey takes you to Cape Cod to explore its rolling sand dunes, dramatic sea cliffs, and picturesque villages. You may also wish to take the ferry (optional, fee applies) to Martha's Vineyard and step back in time while visiting this Victorian era summer resort island. Alternately, you may wish to visit one of the many of the Cape's famous lighthouses such as the Sandy Neck Lighthouse or the Bass River Lighthouse.
Day 10 Cape Cod - Boston Departure
Today, drive back to Boston. You may wish to stop in Sandwich, formerly one of the largest U.S. producers of glass, and visit one of the numerous glass studios, art galleries, rare book stores and antique shops. Or en route you may visit Plymouth Plantation (admission fees apply), a living panorama of Pilgrim times and see the Mayflower II.