Massachusetts
Day Trips

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Our most recommended Massachusetts Day Trips

Boston: Afternoon Sailing Trip Around Boston Harbor

1. Boston: Afternoon Sailing Trip Around Boston Harbor

Embark on a scenic sailing trip on board an authentic tall ship in Boston Harbor. Sailing offers a great family-friendly way to see Boston from a new viewpoint. Choose between a 1.5-hour sail on the Liberty Star or a 2-hour sail on the Liberty Clipper. Hop on board and be transported back to the time when the tall ships would come in from the Old World. You can help set the sails, take the wheel, or sit back and enjoy the passing scenery of the Boston Harbor and the surrounding islands with the city skyline as a backdrop. The Liberty Clipper is a 125-foot gaff-rigged schooner designed after early American privateers. There is a cash-only bar on the ship with beer, wine, mixed drinks, sodas, bottled water, and snacks available. The Liberty Star is another gaff-rigged schooner modeled after 19th-century vessels that were once known for their speed and agility. The vessel offers a similar taste of what it was like to sail the magnificent ships that were once a common sight in every port. 

Foxwoods, CT: 33-Story Building Zipline Flight Pass

2. Foxwoods, CT: 33-Story Building Zipline Flight Pass

Journey to the rooftop of Fox Tower at Foxwoods Resort Casino, 350 feet off the ground. Feel the cool, crisp, air under you as you soar over the treetops at nearly 60mph, arriving a mile away at the Mashantucket Pequot Museum and Research Center, with a smile from ear to ear! There is no other experience in Boston, New York or America quite like it! If you wish to visit the Pequot Museum after your flight, a $10 discounted entry ticket is available for purchase at the front desk. Once your flight is complete, a complementary shuttle will return you from the Musuem landing area back to the HighFlyer ticket counter. Souvenir photos and merchandise are available for purchase before and after your flight.  

Boston: Harbor Sunset Yacht Cruise

3. Boston: Harbor Sunset Yacht Cruise

Embark on a sunset yacht tour of Boston Harbor. Step aboard the classic Northern Lights yacht, a coast guard certified vessel with a captain and crew. The motor yacht Northern Lights is stylized after the classic New England 1920s-style steamships. Sit back and relax in a climate-controlled (with heating and air-conditioning) cabin, or enjoy the sea breeze on the open-top deck. Be sure to visit a fully stocked bar on the main deck to purchase refreshments by credit card, to sip refreshing drinks as you cruise along the harbor. The Northern Lights yacht is one of the most comfortable and versatile cruise vessels in Boston Harbor, at 115 feet in length it features six bathrooms and provides ample seating throughout the ship for up to 149 passengers. Built for taking groups of people on spectacular sightseeing adventures, she is the perfect vessel for taking groups of friends and family out to see the harbor.

Boston: Harbor Codzilla High Speed Thrill Boat

4. Boston: Harbor Codzilla High Speed Thrill Boat

Spark your adrenaline on a high-speed boat ride around Boston Harbor. Ride at break-neck speeds and enjoy the lively atmosphere on board with loud music and crew interaction. This is no ordinary boat ride. True to its name, Codzilla is monstrously fun, a thrill a minute as you scream across the water at up to 40 mph, with a few hairpin turns and 360-degree spins thrown in for evil measure. Take a cruise on the wild side as you scream for more after riding Codzilla. The wind roars, the music blares and the waves will splash during a wet and wild 40-minute ride at full blast. The ride features an original soundtrack and a show scripted by Hollywood screenwriters. Sit back and relax? Not on this cruise. The boat, Codzilla, is 70 feet of marine aluminium and bad attitude, prowling the ocean with 2 turbo-charged diesel engines, state-of-the-art water jets and 2,800 horsepower. Its unique hull design makes it capable of thrilling 360-degree turns and spinning on a dime. So be sure to secure all hats, scarves, eyewear and bad hairpieces. 

From Boston: Martha's Vineyard with Optional Island Tour

5. From Boston: Martha's Vineyard with Optional Island Tour

Start your day with pickup from your downtown Boston hotel in a mini-coach for the 1.5-hour journey to the ferry in Falmouth, Cape Cod. Enjoy complimentary snacks and bottled water while browsing the Martha’s Vineyard guidebook as you plan your 6 hours on the island. After a short ferry ride, prepare to discover the beautiful island. Choose from either joining a 3-hour guided tour or exploring it at your leisure. For both options, you will be provided with a discount card valid at some of the island's restaurants and attractions. Be sure to visit the amazing gingerbread cottages in the town of Oak Bluffs. See the town of Edgartown known for its whaling captains' homes and quaint downtown shops. Head to breathtaking Gay Head Cliffs and see the famous lighthouse in the town of Aquinnah. Bike and jeep rentals are available for purchase or use public transportation to see the island. After your day on Martha's Vineyard is complete and you return on the ferry, sit back and relax on your comfortable minibus ride back to Boston.

Boston: Harbor Champagne Sunset Sail from Rowes Wharf

6. Boston: Harbor Champagne Sunset Sail from Rowes Wharf

Embark on a sightseeing sunset cruise on Boston harbor and soak up the views of the famous skyline. Admire city highlights, including the Inner Harbor Islands and the Boston Fish Pier.    Board an elegant sailing yacht, the ' Adirondack III.' Travel in style on a classic 80 foot pilot schooner that is comfortable and spacious. Glide smoothly over the water and have the option of purchasing a refreshing drink at the onboard bar. Admire views of the historic scenery of Boston Harbor as you pass by the Boston Fish Pier and the Moakley Federal Courthouse at Fan Pier. Capture pictures of Castle Island and the Donald McKay monument. Cruise through the Inner Harbor Islands. Step back in time as you cruise by the historic Charleston Navy Yard. Go by the lush greenery of the Waterfront Park and take in the modern architecture of buildings like the New England Aquarium. Take a selfie in front of the Boston skyline. Have your questions about the sights and history of Boston Harbor and its surrounding areas answered by the attentive crew. Hear facinating facts and old-time legends about the maritime world of Boston. Return to your meeting point at the end of the tour.

Boston: Downtown Harbor Sailing Cruise

7. Boston: Downtown Harbor Sailing Cruise

Experience Boston like never before onboard the 80-foot pilot schooner Adirondack III. Enjoy a round-trip of smooth sailing, with some invigorating speed to boot. Within minutes of leaving dock, you’ll forget the distractions of life on land as you experience the joy of a sailing adventure. Cruise past landmark attractions, such as the Boston Fish Pier, Moakley Federal Courthouse at Fan Pier, and Castle Island. Drift past the Inner Harbor Islands and see the historic Charleston Navy Yard. Look out for the green oasis of Waterfront Park and the home to hundreds of marine critters, including sharks and sea turtles, at New England Aquarium. Your knowledgeable captain and crew will be on hand to answer questions about the sights and history of Boston Harbor and its surrounds, from interesting facts to old-time legends. Wines and local micro beers are available to purchase onboard, while complimentary soda and water will keep you hydrated along the way.

Boston and the Freedom Trail from New York: Day Trip

8. Boston and the Freedom Trail from New York: Day Trip

Depart New York along the Eastern Coast through Connecticut to Massachusetts and to its capital, Boston. Your first stop is the city of Cambridge where will find one of the most famous and most prestigious universities in the world: Harvard. The tour starts with a walk in Harvard Yard; the oldest academic ground in America. See Widener library, then rub the shoe of John Harvard for good luck. Continue to a panoramic tour passing by City Hall, MIT and Cambridge College. Then cross the Charles River and arrive in the center of the intellectual capital of the country. Visit Copley Square, home to beautiful Trinity church. Next up is a walk along the Freedom Trail through Boston Common Park. Break for lunch at Quincy Market, and try the world famous Clam Chowder or a lobster roll. After lunch, visit the site of the famous Tea Party and the navy ship Constitution. In the late afternoon, depart southwest for an evening arrival in New York.

From New York City: Boston in One Day Tour

9. From New York City: Boston in One Day Tour

Come discover beautiful Boston. Have your transportation and itinerary taken care of your while your only job is to sit back and enjoy this stunning city. Explore the best Boston has to offer including: Fenway Park stadium, home to the Boston Red SoxHarvard University Main campus: Harvard Yard, Old Yard, John Harvard Statue, Johnston Gate, Harvard souvenir store.Copley Square: Trinity church, Fairmont Copley Hotel, Boston Public Library, John Hancock Tower, “End line” to Boston MarathonBoston Common and the public gardens  Freedom trail: Massachusetts State house, Old state House, Granary Burying ground, Kings chapel, Faneuil hallQuincy MarketStart your day in New York City where your tour guide will share stories of different places on your journey to Boston. Once in Boston, begin your tour at Copley Square, have lunch at Quincy Market and end the day.

Boston: Fall Foliage Tour

10. Boston: Fall Foliage Tour

Your day will start with pickup from your hotel in greater Boston. From here, you will make the 2-hour ride north into New Hampshire surrounded by the beautiful fall colors as you drive higher into the mountains. You'll make a short stop half-way along for coffee or cider. Once on the Kancamagus Byway, you will make several stops for pictures of the mountains and fall foliage colors. Your knowledgable guide will share details about the region. You'll also enjoy 2 short excursions on easy to hike trails to view historic waterfalls. Then, enjoy a 1.5-hour lunch and shopping break in the mountain town of North Conway. This is a quaint town surrounded by snow-capped mountains and rugged cliffs. After lunch, you'll head further into the White Mountains. The last stop will be near the spectacular Omni Mount Washington Hotel. Many have called this "the highlight of the tour" as this beautiful location neighbors New Hampshire's tallest and most extravagant mountain range. Finally, your guide will point out a few more interesting sights before the 2-hour journey back to your hotel in Boston.

Frequently asked questions about Massachusetts Day Trips

What are other things to do than Day Trips that are worth visiting in Massachusetts?

The other unmissable things to do in Massachusetts are:

Other Sightseeing Options in Massachusetts

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What people are saying about Massachusetts

Overall rating

4.4 / 5

based on 882 reviews

Our cruise was fabulous! The boat exceeded our expectations- no metal benches!- the interior was gorgeous!! Even though it was rainy, we had a lovely time. Service and atmosphere were spectacular! 10/10 recommend!

It was a pleasant experience, the staff was very helpful, and made it very easy when boarding the yacht. I would definitely book one again and recommend it to my friends!

Incredible!!! The view from the top was stunning. You really do “fly” down to the bottom. Def an experience for the books!

It was absolutely lovely. Very chilled out. Lots of space on upper deck. Great bar. Lovely vibe. LOVED EVERY MOMENT.

Staff are fabulous. Some rude passengers but that can't be helped.