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    Classic Harbor Line Boston

    4.7 (171 reviews)
    Closed 10:00 am - 9:00 pm

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    Reviews With Photos - Classic Harbor Line Boston

    We had a blast sailing
    Michelle P.

    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!

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

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

    Adirondack II

    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!

    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.

    Lovely centerpieces you can use for your event.

    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!

    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

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    1 year ago

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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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    A must do in Boston. So incredible and relaxing. I loved every minute of it. The crew was excellent.

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    7 years ago

    Gorgeous boat and perfect sail, but the cocktail carrot is predatory. Make sure you read the fine line. Otherwise, beautiful voyage.

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    Page 2 of 5

    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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    Classic Sail

    Classic Sail

    4.9
    (55 reviews)

    Captain Dave is the kind of guy that not only oozes knowledge of sailing, the route, and…read moresurroundings on your trip, but he also fit into to group seamlessly and doesn't feel like an outsider... and that makes it feel like you're on the water with a bunch of friends and one just happens to own a boat. First, we had to reschedule our trip from last year as I was hospitalized and unable to make the original trip. My wife contacted Dave and they refunded us initially without hesitation. These are not only professionals, but people with kind, large hearts. The policy could have easily taken our money but we were able to reschedule and not have to pay any additional fees or money given our extenuating circumstances. The boat is clean, well-kept, and the comms and instructions were passed along early and with plenty of detail to leave no room for misinterpretation. Payment and scheduling were easy (as my wife told me, at least) and expectations were set as to what was (and was not) provided in the cost. As far as the value and trip itself, it's money well spent. We've done dozens of chartered routes along the coasts as well as in the Caribbean when we travel. Captain Dave was easily in the top 3 in terms of overall experiences and how effortless the day felt. It wasn't too long or too short, and Dave made sure to capture plenty of moments and memories for us instead of all our photos missing one (or more) members of the group. We also got to stop at 2 of the islands and swim around for a bit at each of them before returning back to the docks. There were 6 people in our group and we had plenty of space for all of us, 3 backpack/YETI soft coolers, and about 4 bags of food/snacks. There is also a shaded area if you forget sunscreen and/or just need to get out of the wind or sun. If you're curious or wondering if you may enjoy an experience like this, my best advice to you is just book it and don't overthink it. It surpassed all my expectations and was a blast of a way to spent a hot, sunny Saturday in the summer. Given the other reviewers' experiences, it doesn't seem like anyone has had a bad experience with any of the captains either. If you have anywhere near the experience I did, you'd be okay with paying double what we did for the day... it's just that much fun. Thank you to everyone at Classic Sail for the kindness, understanding, and above all - the awesome product/experience. You've made a few new fans in the Boston area!!!

    What a great experience! We sailed with Captain David on a beautiful day in early May. Because my…read morepartner has such a strong desire to learn to sail, he asked a lot of questions to learn about the vessel and different verbiage. David enthusiastically answered every question, while also giving us lessons on different sights around the sail. Highly recommend - hope we can make it back another day!

    Boston Yacht Charters

    Boston Yacht Charters

    3.4
    (8 reviews)

    Planning a special event on the water? Don't look any further! Ann at Boston Yacht Charters was…read moreAMAZING in helping me plan a surprise private charter for my boyfriend's bday and our anniversary! Not only did she coordinate an amazing afternoon on the harbor with Captain Don on the Indiscretion, she became my Boston tour guide helping me plan the perfect trip and walked me step by step through transportation, restaurants, neighborhoods, live music venues, etc. She is a true Bostonian, LOVES her city and should be named Boston Ambassador Extraordinaire! Ann made sure we had our favorite snacks, champagne, glasses, etc. and Captain Don had a cooler full of beverages and even offered to cook on the grill for us while on our 3 hour trip around the harbor. We visited Boston over Halloween weekend 2021 which was late in the season to charter a yacht. Ann communicated with me almost daily leading up to the trip and worked with various captains to ensure I would be able to surprise my boyfriend with a special day on the water...we even worked together to move the timing of the charter during our trip ensure we had the best weather for our excursion. Ann met us at the dock, took photos and took care of all the details, making it a wonderful surprise, within our agreed budget and helpful in every way. Huge thanks to Ann for her OUTSTANDING customer service and genuine interest in helping me plan a day that my boyfriend (now fiance) and I will never forget, and a special trip that we will always cherish.

    Recently booked a company outing with Ann at Boston Yacht Charters and everything worked out great…read more We booked a 2.5 hour harbor cruise on the Timeless through Ann who coordinated everything for us and worked within our budget. All we had to do was show up at the dock. There was plenty of food and drink (both of which exceeded expectations) and the staff of the Timeless were extremely friendly and accommodating. This was our 3rd time working with BYC and i foresee us returning again.

    Boston Harbor City Cruises

    Boston Harbor City Cruises

    3.4
    (14 reviews)

    Took my husband on the Spirit of Boston the other day. It was his first time. The boat is huge,…read morethree levels! We arrived right before departure, they are very prompt so make sure you're on time. The buffet was good, lots of options! Certain dishes were bland, just need more seasonings. But overall I was stuffed! Desserts come after dinner is done. It has a full bar and live DJ for some dancing. We had a good time! It's definitely a Must-Do in Boston!! Parking tip - the closet garage is right across from the dock 155 Seaport Blvd.

    I recently took my visiting family on a Spirit of Boston Dining Cruise for Dine Out Boston, and the…read morespecial price of $55 per person was an absolute steal! The trip alone is worth more than $55, so the additional food was just a bonus. Based on the menu I saw online, I was expecting a 3-4 course meal, but I was pleasantly surprised to find that the dining experience was buffet style. This meant we got to sample a lot of the delicious food! My favorites were the salmon and the chicken, and for dessert, I really enjoyed the peach cobbler (not pictured) because I couldn't resist devouring it before snapping a photo. When the buffet first opens, people rush to the line and it gets a bit crowded. My tip: let the hungrier people go first to avoid the claustrophobia. We also purchased a margarita for two, which was so huge that the three of us couldn't finish it! We even got a margarita mug with the City Cruises logo as a souvenir. There was a DJ playing cool music while we ate, and the servers were fantastic, bringing us drinks and quickly removing empty plates. The best part was undoubtedly the nearly 3-hour cruise around Boston, where we got to see a lot of landmarks. My family loved it, and it will definitely become a tradition whenever they visit Boston.

    Classic Harbor Line Boston - tours - Updated August 2026

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