Boston Harbor
Day Trips

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Our most recommended Boston Harbor 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. 

Boston: Harbor Sunset Yacht Cruise

2. 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

3. 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. 

Boston: Harbor Champagne Sunset Sail from Rowes Wharf

4. 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

5. 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

6. 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.

Boston: Cocktails, Rum, & City Lights Cruise

7. Boston: Cocktails, Rum, & City Lights Cruise

Join this tour for an after-hours boat cruise in Boston. Relive the tall tales and true stories of pirates and patriots who sailed Boston Harbor in the 1700s. Be transported back in time through sea stories, tavern jokes, and music of the revolutionary period when the American colonies fought for their freedom from the British. Unwind on a Saturday evening as the cruise brings the Caribbean to you. Marvel at Boston Harbor and its surrounding islands on the Liberty Clipper, a 125-foot gaff-rigged schooner designed after early American privateers. Enjoy the sparkling lights of the Boston skyline while listening to the shanties of old onboard a schooner. You can help the crew haul up the sails to a sea or just enjoy your drink and relax. Experience the sounds of times gone by as you sail on a grand tall ship. Once you are onboard, place your orders for the bar. Try the sailors’ favorite— a Dark ‘n’ Stormy, featuring Gosling’s dark rum, ginger beer, and a twist of lime. Or order from a menu of other cocktails, beer, wine, and non-alcoholic refreshments.

Amazing Scavenger Hunt Adventure: Boston Harbor

8. Amazing Scavenger Hunt Adventure: Boston Harbor

Looking for a way to turn Boston Harbor area into a giant game board?  Come experience an interactive scavenger hunt that combines the fun of the "Amazing Race" with a three-hour sightseeing tour of the Harbor area. Guided from any smart phone, make your way among well-known and overlooked gems of the city, solving clues and completing challenges while learning local history. Your Boston Harbor amazing scavenger hunt adventure will begin at a serene labyrinth on the Rose Fitzgerald Kennedy Greenway and take you to historic wharves and parks with outdoor art. You'll be introduced to a small herd of seals, and view scenic harbor vistas. The game route will have you strolling down the Greenway and exploring historic harbor sites including the location of the Boston Tea Party, as the game shows you some of the best sights and hidden gems of the city. Using a smartphone as “the guide” allows participants to start when they want and determine their own pace of play. Stop for lunch along the wharf or take a stroll on one of the shaded trails of the park… why not, it’s your schedule! Offered at a fixed price for a group vs. per person pricing, this city tour/game offers a great value to those on a budget.

Frequently asked questions about Boston Harbor Day Trips

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Other Sightseeing Options in Boston Harbor

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What people are saying about Boston Harbor

Overall rating

4.5 / 5

based on 701 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!

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

Fantastic experience! Crew was excellent! They were all friendly, informative and accommodating!

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