This was one of the highlights of our trip to Boston! The crew was incredible to watch as they worked the sails. The deckhands were full of energy, especially Alex--you could tell he truly loves being out on the water. He also took the time to point out and explain the landmarks we passed while sailing around the harbor. I can't recommend this experience highly enough! read more

It was fun and enjoyable the crew was great. It was a very windy day. It was our very first time going on a sail boat. And it will not be our last. Again great experience. The crew was Michael, Alex and we didn't travel the third name but, it was 2 guys and a girl. read more

The crew, Captain Mike, Alex and Charlie were fabulous. We motored out a bit and then set sail. The quiet that came when the engines turned off and we were sailing with the wind at sundown was an indescribable experience. The crew could not have been more knowledgeable, experienced, attentive and receptive to us. This is an experience that I have done twice with this company and Captain and hope to do many more times. I highly recommend it. My out of town guest was blown away by the sites of the city from the water, with the vessel and the crew! read more

I found the tour to be beautiful and was excited that it was 3 women on deck including the captain. The 2 women in green (deckhands) were nice and informative. However, the captain didn't speak to us at all even after we said thank you, she couldn't even make eye contact. I did notice her speaking and being polite to the white passengers. read more

Classic Harbor Line Boston - Captain of sailboat - Tours Near Me - Boston, Massachusetts

Amazing views, loved how the captain was talking to us about some history. Great conversation and great company! read more

Classic Harbor Line Boston - Tours Near Me - Boston, Massachusetts

The day sail was awesome! Kira and Alex were so nice and really knew what they were doing. The service was quick and exceptional. I would definitely come back on this boat! They made the ride fun :) read more

We had a perfect sail around the Boston harbor! They actually sailed without the motor! The captain and the crew were amazing and the boat had the perfect amount of guests. I would do it again when I'm back in Boston! read more

Classic Harbor Line Boston - We had a blast sailing - Tours Near Me - Boston, Massachusetts

We had a fantastic time!! The tour was organized and on time, the crew was Fantastic. We opted for the oyster tour, which was a lot of fun. When booking, there was a 21+ note (we have a 12yo who loves oysters and can absolutely behave with adults). I called and it was confirmed for all-ages (just no alcohol for those under 21) and was able to take my booking over the phone. The weather wasn't great - some rain, but the captain and crew were prepared with ponchos for those who wanted them - and even better kept the drinks flowing and the laughter and fun never stopped. Would absolutely do another event with the Classic Harbor Line. read more

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Enjoyed the 2 hour tour of the bay with brunch. Definitely worth booking. The boat was clean and the staff was great.

Very professional team allows us to relax and enjoy the cruise. Clean ship and very informative read more

My ride on the Adirondack Day Sail was beautiful, stunning, and memorable fun: the best part of my 4th of July weekend, and one of the most delightful 1.5 hours in Boston, ever. The captain and crew were gracious. The crew offered hospitality and information about the sights in Boston Harbor -- all while managing impressive, large sails -- and the captain had an expert way of finding fabulous waves and delightful wind to make our ride at once relaxing and refreshing, but also exhilarating. I highly recommend this special adventure: the price is right, and the experience priceless. read more

Had an excellent and safe cruise on Sail Boston 250. Got nice views of the tall ships. read more

Classic Harbor Line Boston - Tours Near Me - Boston, Massachusetts

Friend and I went on the oyster sail and had a great time! Everyone was so nice and helpful! I would highly recommend for a fun boat ride and would go again! read more

Classic Harbor Line Boston - Adirondack II - Tours Near Me - Boston, Massachusetts

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Excellent cruise on last morning of Boston Tall ships..great narration of the remaining ships and excellent weather as well. Highly recommend,Mike Kelliher read more

Classic Harbor Line Boston - Tours Near Me - Boston, Massachusetts

Charlie, Hannah and Eric were amazing. Great fun, great service and lots of fun. This is worth your time in Boston!

I had such a great experience on the Adirondack day sail. I don't know much about sailing so I didn't know if the weather conditions were going to be suitable for actually using the sail but apparently they were! Besides pulling in and out of the dock, our sail was up the whole time! I was also impressed that the crew gets up and walks around to take drink orders and bring them to you, I wasn't expecting that kind of service. I got rosé and it was good! Overall so fun, now I want to go back and try the sunset experience! read more

Classic Harbor Line Boston - Tours Near Me - Boston, Massachusetts

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At first it seemed kind of expensive, but it is so worth the price. The Schooner is beautiful and comfortable boat. It was a beautiful day and when the sails were up an the engine was off, it was quiet and so lovely. The oysters and shrimp were delicious. It is so much better than the motor cruise which stinks like diesel and is loud. Treat yourself to this one!!! read more

pretty chill~ could always see airplanes flying above us. Nice crew people who introduced the places we passed by.

We had a brunch boat trip this past Saturday on The Northern Lights and it was perfection. The food was varied and delicious. The boat gleams and the staff were so wonderful! It was a fantastic experience! We can't wait to go again next month for our 50th Wedding Anniversary celebration! read more

Classic Harbor Line Boston - Lovely centerpieces you can use for your event. - Tours Near Me - Boston, Massachusetts

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Went out on the Adirondack III the last day of Sail Boston. It was a very pleasurable cruise with an exceptional crew. Crew provided a high level of service and was knowledgeable, providing the right mix of quiet and tour knowledge. Boat was clean, service top notch. Boat was full, but did not fill overcrowded. read more

Went here with friends on a cruise Sunday evening, where the weather forecast was windy and cool weather. Despite this, we still enjoyed the tour and really appreciated the fact that we were able to sit inside and still get a view and a seat. There were other lines we looked at that seem to be busier so we really enjoyed how uncrowded this tour was the boat takes you on a tour of the surrounding harbor and explains all of the sites and history. You even get to see a cannon launched. They have drinks and snacks for sale with a couple of differing options on the top of the boat. We were disappointed that they did not have more warm drinks such as hot chocolate. They hey also do not advertise that they have some different options above. Another thing I wish, was that the windows were larger from the inside of the boat, as it was extremely windy when going outside and frigid. read more

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One of the best short sightseeing cruises I have been on. Well managed, informative and fun. Of course because it viewed the Tall Ships it made it exceedingly special. 5 Stars! read more

My son and I took the Harbor Cruise on the Patriot yesterday to see the Tall Ships in Boston Harbor. The boat holds a maximum of 25 passengers, and therefore, is a very calm environment for the tour. It is also a comfortable boat. Eric, who was manning the wheeel, got us as close as possible to each ship and navigated safely in a busy harbor. The crew was great. Do yourself a favor and book a cruise with them! read more

We just came back from an exceptional sail on the Adirondack II to see the Tall Ships in Boston Harbor - the sunset cruise. It was so wonderful and just the very best experience! Our captain, Stitch, and crew of Hannah and Charlie were so helpful and knowledgeable. I highly recommend! read more

Really terrific experience! The logistics of getting to the offices for the ticket and then to the boat launch was so much easier than expected. We chatted with the crew and Classic Harbor Line team member (shout-out to Bob and Old Bob) for a while before boarding. They were so friendly and knowledgable about the boat and location. The captain filled us in on the local boats as well as some history about the local ship building) as we sailed past. The nicest part - turning the engine off and actually sailing (with the sails). Too many "sailing" excursions do not actually sail! This one did and it was great. read more

We took the patriot around the harbor to get a good look at the tall ships. The crew was great. The captain did an amazing job steering through the chaos of Boston harbor. read more

We took the Patriot and the crew was awesome. It was a small yet comfortable ride. Great night on the water in Boston Harbor.

Dante, Claire, Charlie, & Matt were a FABULOUS crew!! So willing to be helpful and incredible friendly. You can tell they really love what they do. Thanks so much for a memorable first sailing experience! read more

My family were on the Cocoa and Carols Holiday Cruise in Boston. Great atmosphere including music being played by live band. Cocoa station was a nice set up. Views of City were nice as well read more

Amazing crew. Beautiful sail. Captain let out 7 year old "take the helm" and the drinks were cheaper then on land! Well worth it

The wonderful sail was beautiful with the perfect sunset and amazing scenery. The crew were very nice and had patience with everyone answering all questions with a kind tone. The captain Dereck was willing to answer and share his experiences with the passengers. The crew told their stories of the tales on the ship and handed drinks out for everyone to enjoy. Alex was a very patient man who helped me answer questions, heather was kind sweet and very helpful with sails along the boat, and Claire told stories about the fort and the islanders sharing knowledge of what was filmed and experienced in the harbor. read more

We loved our afternoon sail aboard the Adirondack III. The crew was very accommodating and fun. It's a laid-back sail that's safe for everyone. We had a low-wind day with a full boat, which was very calm. It's magic to be on the water with just the sound of the lapping water and sails. This experience is accessible for all ability levels and is very family-friendly. It's an enjoyable ride for all members of your crew. read more

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Such a fun time everyone should do it once at sunset very informative and educational

We took a sunset sailing cruise with Classic Harbor Line Boston on August 26, and are so glad we selected them! Amazing experience! The crew was super friendly and attentive, and you aren't on a large ship crammed full of people. Another bonus: The Classic Harbor Line sunset sailing cruise lasts 1/2 hour longer than the one provided by the other "popular" cruise line in the area. We watched the other sunset cruises heading into port while we continued to relax and enjoy the pleasant evening and beautiful city lights from the harbor. I'd venture to say this cruise was the highlight of our Boston trip. Highly recommend!!!!!! read more

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We came on the Northern Lights ship because our other booking on the "floating ballroom" was canceled, and we are SO GLAD we went on this cruise. We found out later it is a family run business...and they get their beautiful boats which are made on the Hudson River in New York. Beautiful ship with gorgeous natural wood inside. The main indoor room has a nice bar, and a really nice setup of the tables, for groups big or small. The buffet brunch was REALLY good, with delicious home fries, quiche, delish croissants and danish (not boxed), salad, French toast, yoghurt parfaits, and so much more!! They have a coffee bar with very good coffee, and tons of cocktails and mocktails to choose from...along with lots of beer. The staff was really nice and helpful. I would totally do this again when we have visitors come into town. Well done and we'll certainly be back! read more

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Had a great time! Theresa was very knowledgeable in general, and it's cool to learn about her past in sailing. Great crew on board!

This was awesome!!! The service was so nice and fast, the band was AMAZING, and the skyline-oh, the skyline!-it could not be beat (See picture below). This is a must-see if you ever come to Boston! Thank you, Classic Harbor Line!!!!!!!!! read more

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Wonderful outing for our staff. The crew is knowledgeable, friendly and hard working. No better place to be on a sunny afternoon then out in Boston Harbor! read more

We did the 1:30pm sailing on the Adirondack II and it was wonderful. Terez was our captain and she was knowledgeable about the area and very friendly. The crew was amazing as well. I would definitely recommend. read more

My husband and I thoroughly enjoyed the Sunset cruise on Boston Harbour. Our arrival at the USS Constitution to watch the flag lowering and the gun firing (to signify sunset) was timed to perfection. The onboard commentary was fantastic and the crew were enthusiastic and helpful. Thank you for a wonderful experience. read more