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New England

View On Map Travel Tips

This coastal cruise will take you through a string of quaint towns and big bustling cities of the USA’s eastern seaboard. As you drive from Boston, Massachusetts to Freeport, Maine, give yourself time to stroll along the sandy beaches, soak in fresh sea air, saunter through old sea captains’ and artists’ colonies, and enjoy plenty of fresh, delectable seafood!

The historic city of Boston is the starting point for this amazing drive. Visit the Skywalk Observatory for 360˚ panoramic views of landmarks like Fenway Park, and the Boston Common. Walk down Beacon Hill’s cobblestone Acorn Street, one of the most photographed streets in the USA.

Once in Salem, Massachusetts, climb the secret staircase in New England’s oldest surviving 17th century wooden mansion, The House of the Seven Gables, the inspiration for author Nathaniel Hawthorne’s novel of the same name. Nearby Marblehead is a picturesque sailing town famous for its original, 105-foot-tall cast-iron light tower.  Drive 45 minutes north to charming Newburyport, where delightful inns line the streets and restaurants like Brine serve fresh seafood caught from the local docks.

The next stop: Portsmouth, New Hampshire. Downtown, check out the landmark Music Hall, a Victorian theatre known for showcasing world-class entertainment for more than 135 years. In the neighbouring town of Rye, visit Wallis Sands State Park and take a dip in the Atlantic. Rye boasts the longest stretch of coastline in the state!

Travelling into Maine, Kittery is the state’s oldest town and an excellent spot for admiring charming cottages. Water activities reign supreme here, so take a sunset sailboat charter, embark on a deep-sea fishing expedition or even a little whale-watching cruise.

The pristine town of Kennebunk has all the nostalgia of old world New England.  The historic Colony Hotel is a picturesque getaway built in 1914, and is a perfect spot for a cool drink, sweeping ocean views and luxurious accommodation. Rent a bike and ride to Goose Rocks Beach. Then stroll around Dock Square, and meander through antique shops and art galleries. If you love architecture, stop at the Wedding Cake House—the most photographed house in Maine. Created by a local shipbuilder in the 1800s, it’s an ornate Gothic Revival structure with carved buttresses, spires and lacy spandrels.

Your last stop in Maine is Freeport. Here, take in the splendour of the majestic rocky shoreline peppered with lobster boats. Ten minutes from the hustle of Freeport’s busy shopping area, Wolfe’s Neck Woods State Park is spread over 200 acres and offers fantastic hiking, picnicking and wildlife watching. Don’t miss Freeport’s L.L. Bean flagship store, founded in 1911 by Leon Leonwood Bean and credited for the company’s iconic waterproof duck boot, still worn today.  “Maine Lobster Sunday” is a weekly tradition at the Harraseeket Inn’s Broad Arrow Tavern. Make sure to grab a reservation before you take a seat at this delicious restaurant.

What to bring: an appetite for fresh seafood, a camera to capture all the New England charm, and beachwear depending on the time of year.


View On Map

Basic Route Information

Route Distance 281 Kilometers
Route Time 4 Hours
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