The Perfect Boston Day Trip for Travelers Who Hate Planning

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Surrounded by seaside towns, cool beaches and endless natural wonders, Boston is America’s oldest and most iconic city that continues to transform itself over the years.

Boston also happens to be a popular embarkation and disembarkation port for cruise itineraries, and is filled with fabulous places to visit on a day trip to Massachusetts.

If you are planning to go on a cruise from Boston, there is plenty to see and do before or after your voyage. Even though this destination gets booked up early year-round, there are plenty of day-trip options for those planning to travel at the last minute.

Newburyport, Massachusetts

Massachusetts, Newburyport, Historic coastal town with brick streets, waterfront views, and the lively Market Square district
Photo Credit: Deposit Photos.

For those looking for a quick quintessential New England seaside town getaway, Newburyport has to be right on top of the list.

Located north of Boston, with convenient rail connections, Newburyport is known for its spectacular waterfront and vibrant downtown area with access to the beach and the wildlife on Plum Island. It is one of many beautiful Massachusetts destinations worth exploring outside Boston.

Newburyport is itself very walkable and you can easily explore attractions like Oldies Marketplace, Custom House Maritime Museum and Cushing House in a day, before heading back to Boston.

Lexington

History buffs will remember that the first shot of the Revolutionary War was fired in 1775 in Lexington. Head out on a day trip, some 30 miles from Boston, to explore a wealth of interesting historical sites, including the Lexington Green battlefield and Buckman Tavern.

If you get tired of waiting, ride on the legendary Liberty Ride Trolley, which passes through all the above sights and some more like the erstwhile home of Ralph Waldo Emerson.

During the highly educational ride, a knowledgeable guide will share interesting tidbits and stories connected with Lexington on board.

Cape Cod

Cape Cod Provincetown beach Massachusetts USA

Around 90 miles from Boston, Cape Cod promises the ultimate respite for those planning to spend a day under the sun and on the beach on a warm summer day.

At Cape Cod National Seashore, you can hike or check out one of the famous American lighthouses or participate in a ranger-led program.

Besides the seashore, Cape Cod has art museums, seal watching boat trips and some excellent restaurants where you can enjoy top quality food. This is the perfect place for a spontaneous trip where you want to squeeze it all into one day.

Martha’s Vineyard

Carpenter Gothic Cottages with Victorian style, gingerbread trim on Lake Avenue, Oak Bluffs on Martha's Vineyard, Massachusetts, USA.
Photo Credit: Deposit Photos.

This is a must-explore town, but keep in mind that if you are going in summer you will find tons of traffic heading down the Cape.

Start your day with a visit to the beautiful town of Oak Bluffs to explore the pretty gingerbread houses. Next head to Edgartown and catch the ferry to Chappaquiddick Island and explore it on a rented bike.

Late in the afternoon, you can check out the stunning Aquinnah Cliffs and Mashup beach, followed by a sunset trip to the charming fishing village of Menemsha and Vineyard Haven. It is easy to see why Martha’s Vineyard ranks among the best islands in America.

While most of the above day trips from Boston can be done by car, several of them can be done by public transport as well, making it easy to explore some of the oldest places in America.

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Catherine, a seasoned travel writer, has lived in 4 different states and explored 36 states and 28 national parks. After spending two years embracing van life, she's now dedicated to sharing her vast knowledge of day trips across America. Catherine's other works has been referenced in major publications like MSN, Self, and TripSavvy.

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