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    Classic Harbor Line Boston

    4.7 (156 reviews)
    Closed 10:00 am - 9:00 pm

    Services - Classic Harbor Line Boston

    Boat charters

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    Oysters and Shrimp
    Michelle B.

    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.

    Brooke C.

    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!

    Ashley C.

    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.

    Bridges at sunset, taken from cruise

    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!!!!!!

    Adirondack III sailing boat
    Dawn C.

    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.

    The INCREDIBLE live band.
    Preston C.

    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!!!!!!!!!

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    6 months ago

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    Caleb P.

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    16 hours ago

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    Caleb P.

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    3 days ago

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

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    10 months ago

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    11 months ago

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    8 months ago

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    10 months ago

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

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    10 months ago

    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!

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    2 years ago

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    9 months ago

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    9 months ago

    This was an awesome, relaxing and quiet trip. The crew was super friendly and helpful. We enjoyed every minute.

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    9 months ago

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    10 months ago

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    9 months ago

    Great brunch cruise! Great boat, food & gorgeous views. Very relaxing & nice clientele & staff. Would do it again!!!

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    1 year ago

    Fantastic crew - very personable and attentive. The weather wasn't great but the guys still kept everything upbeat and enjoyable.

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    Page 1 of 4

    Ask the Community - Classic Harbor Line Boston

    Review Highlights - Classic Harbor Line Boston

    Decided to book a sailing with the Adirondack III as a way to celebrate the beautiful weather we were having.

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    Boston Duck Tours - The Captain giving his speech

    Boston Duck Tours

    (1.2k reviews)

    Back Bay

    Coming from California, I had thought we were going to go duck watching. Another thought we were…read morepaddling around in a kind of swan boat. Turns out the Duck Tours were tours in semi-aquatic buses that mix history, jokes, and sightseeing. We also got to go into the water and folks took turns driving the duck boat. What was delightful about our tour was our captain who entertained us with magic tricks, punny jokes, dad jokes, and history. We quacked at passerbys, other duck tours, recent graduates, kids in hi-vis vests. He pointed out the marines organized in a park with the Osprey and other planes. I left my knowledge of American history in elementary school, so everything was super fascinating to me. I thought my honey would enjoy this being a historian and all but he didn't care for the jokes, which I thought were the best part. Oh well. Worth a tour when you're in the Boston area!

    We enjoyed our Boston Duck Tour earlier this month and the tour itself was amazing. Our narrator…read more(The detective?) and the driver were fantastic and our whole family was laughing the entire time. When I took my kids on the tour in 2019, I was so impressed with the professionalism of the attendants who help out beforehand. They were all wearing khakis, had their shirts tucked in, and there were no phones in sight. I remember one lovely young man who was wearing a Vineyard Vines belt and my son was obsessed with it, and he graciously told me what the print was called and I was able to purchase it for him for Christmas that year. This time around, it was shocking to me how opposite our experience was pre-tour. I recall in 2019 receiving a warm welcome walking up to the boarding location, but not this time. They were all huddled in a pile by the umbrella, and no one greeted us. I approached an employee who identified himself as a driver and instead pointed me to an attendant who could "better assist". When I asked which boat to board, we were rudely told to "Just wait here until we announce it", which felt like a big departure from the friendliness of a few years ago. The attendants themselves just looked messy, and it seems the standards went down significantly. We had so much fun on the tour itself, but the end to end of an experience is really what makes or breaks it, and the bad customer service before boarding left a sour taste in our mouths.

    Mobsters And Lobsters - At the final designation, eating "LABSTAHS"

    Mobsters And Lobsters

    (35 reviews)

    Downtown

    The party bus!!! So fun. One of the best birthday experiences I have had. You can book the bus for…read morea minimum of four hours and as many stops as you would like. our bus driver was great and incredibly helpful. He knew of extra bars to stop by that do not include covers and free shots for the birthday person. He also stopped for hotdogs at one point. it is byob and your own playlist. There is truly no experience quite like it where you can jam to music and drink, while driving around Boston. Would recommend for any occasion.

    Holy shit, what a gas... As part of our social engagement…read morefor work. We were designated to go on a bus tour of the Boston scene. Not necessarily the usual Boston, the underground Boston. Mobsters and Lobsters is a mafia story laden trip that ends up at the south shore popular lobster eatery. Although Mother Nature and the traffic in downtown Boston decided yo play games with us the owner who's name actually is Tom Collins, started off with a quick quip yo get the folks settled and the first round of beverages were begun. Tom brings us around to the spectacular locations and spots where specific mobsters from the years past were doing their cunning and not so cunning work. Tom's knowledge for this thoroughly interesting topic is unmatched. His serious knowledge of the history of other significant historical places and events speckled with his dry "Bastan" humor. Made this trip extremely worthwhile. The duration was four hours long which also included a Lobster dinner at a local eatery on the south Boston harbor. I haven't laughed this hard in a long while. If you are in beantown for a spell. I highly recommend you and you motley crew join Tom for an interesting alcohol added trip back in time. I am positive your jaws and cheeks will be sore from laughing so hard. Be aware this is an "R" rated trip! But very worth it. Thanks Tom for making this a great memorable evening.

    Boston's Politically Incorrect North End Food Tour - The best Sfogliatella I ever had!!

    Boston's Politically Incorrect North End Food Tour

    (184 reviews)

    North End

    Tony is a true treasure. He loves his neighborhood and it shows. He will take you to places that…read morework to keep the North End a real neighborhood. The food is some of the best I have ever had and they aren't small portions. Come hungry for good food and great stories of what makes the North End a special place. It's a dynamite experience from a guy who is not only a local, but I am pretty convinced he's the unofficial mayor of the neighborhood based on the number of people who said hello (and other stuff unsuitable for small children or church) to him as we walked the narrow streets. You'll even learn some new curse words. Anthony, your tour guide, doesn't hold back what he thinks.

    I have a bone to pick with Politically Incorrect North End Food Tour.... It was so so good that it…read morehas ruined every other food tour for me.... Anthony has set the bar way too high. Now this tour may not be for everyone, as the title of the tour alludes to.. but if you don't mind the random swear word and aren't easily offended, you'll be like me... cracking up for 3 hours straight. And there was one thing I noticed about Anthony that he doesn't advertise, and may try to track me down for saying on here.... But beneath the gruff exterior was the sweetest guy that seemed genuinely interested in sharing his culture, stories, and amazing food with everyone! We started off at a pizza joint where we got a slice of pizza and an arancini ball. I expected the pizza to be good... and it was fantastic. But I am not a huge fan of arancini and this one had peas in it... also something I am not a huge fan.... But hey, I was on a food tour so I was going to try everything! Thank goodness I did, because this arancini was the stuff of dreams. How in the world could something be THAT much better than what high end Italian restaurants advertise? The last time I had an arancini ball was at a restaurant in Hawaii that won "best Italian food in Hawaii".... And it was only so-so. This arancini ball would make me fly 5,000 just to eat it again! Next up was a deli sub, a coffee shop, ravioli, a pastry shop and lastly an affogato (or gelato if you didn't want coffee that late in the day). Based on the food I received, before factoring in all the stories that Anthony shared, I feel the tour was really underpriced. I wish I hadn't done this the tour on my last day, I would have gone back for another round of everything we tried, as well as everything that was recommended. Heck I may have signed up for the tour again just to experience it all over again!

    Charles Riverboat - An intimate surprise engagement aboard Happy in Boston Harbor.
 @jasoncoreyphoto

    Charles Riverboat

    (151 reviews)

    East Cambridge

    My wife and I were married on the Henry Longfellow. It was an incredible evening. The family and…read morefriends that joined us, the amazing staff, and our first mate/onboard manager Allison made it a night we will truly never forget. Thank you again to everyone that made that night so perfect! We want to give a special shout out to our event coordinator, Kaitlin. We initially had two separate venues for our wedding. We planned to have just the reception on the Henry Longfellow, while the ceremony takes place in Boston. It was only a month out from our wedding day, when our ceremony venue fell through and we had to scramble to find an alternative solution. During that stressful time, Kaitlin did an amazing job working with us to combine our ceremony and reception on the Henry Longfellow. She was comforting, accommodating, and a joy to work with. We couldn't have planned our wedding without her! The absolute best!!! Sincerely, Brian & Katy

    We had a good experience with charles river cruise in our recent trip to Boston. The boat dock was…read morenext to a shopping mall with access to restroom, dining options and various shops. The receptionist was friendly. The tour guide was phenomenal. Bearing a great, easygoing and a bit sarcastic personality, she was engaging, knowledgeable, funny and honest about her delivery. I learned a few things about the city and the famous schools from her personal opinion. Very steady and peaceful ride. Clean and well-maintained boat with a bar. Be mindful it's hot inside the boat with the scorching sun in PM so bring water, sun screen and hat, dress lightly. It was our second day in town our bodies still adjusted humidity and heat, I felt I was about to get a heat stroke. It'd be nice if they consider AC operated boat in the future.

    Tipsy Chocolate Tours - Chocolate Guinness Pint

    Tipsy Chocolate Tours

    (8 reviews)

    Back Bay

    We really enjoyed this chocolate tour. Anne is a great tour guide and very knowledgeable about…read morechocolate and the history of Boston, we learned a lot. We went on the two hour Back Bay tour and sampled chocolates, wine, tea, and ended with the best chocolate martini I've ever had! I would highly recommend this tour for the chocolate lover!!

    So first off, I'd like to start with the positive. Our tour guide was fantastic. She was infectious…read morewith her smile and so personable, so let this rating be of no reflection to her. It's who ever hosts this tour and is making the bank on it, it's all sorts of upside down on the expectations vs reality. I had an expectation we would actually be trying lots of chocolates, instead we went to 3 diff places, and had parts of a broken chocolate bar and then had a chocolate martini at the end. Probably adding up to a max $20 total for the actual chocolate we ate. It was disappointing. For $73 I was expecting to actually try chocolates (similar time a wine tasting) and learn what brings out certain tones in chocolate. Instead they took us to 3 chocolate stores (one in a strip mall and one in a tiny liquor store) and basically tried to sell us chocolate from those stores with the incentive of 20% off. I wasn't looking for a coupon, I wanted a real tour that would be a great birthday feature for my friends who flew into town for this occasion. We felt ripped off and sold to, and instead of being a great occasion, it set a horrible tone for the weekend. :/ Totally regret. Don't expect chocolate on this tour, and deff don't expect "tipsy" unless 1 choc martini at the end gets you there.

    Classic Harbor Line Boston - tours - Updated May 2026

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