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    Classic Harbor Line Boston

    4.7 (180 reviews)
    Open • 10:00 am - 9:00 pm

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    Captain of sailboat
    Jos S.

    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.

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

    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!

    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.

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

    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!

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

    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!

    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!

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    1 month ago

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    Caleb P.

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    21 days ago

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    Caleb P.

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    24 days ago

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    22 days ago

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    13 days ago

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    2 months ago

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    1 year ago

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    2 months ago

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

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    Caleb P.

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    2 months ago

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    20 days ago

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    2 months ago

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    3 months ago

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    3 months ago

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    3 months ago

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

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    1 year ago

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    2 months ago

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    4 months ago

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

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    Caleb P.

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    5 months ago

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    Caleb P.

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    3 months ago

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    3 months ago

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    3 months ago

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

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    3 months ago

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    10 months ago

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    5 months 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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    4 months ago

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    1 year ago

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

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    1 year 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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    Page 1 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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    Boston Yacht Charters - Schooner LANNON...49 Guests, Gloucester MA ~

    Boston Yacht Charters

    (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 - Ticket area buy online and I waiting

    Boston Harbor City Cruises

    (473 reviews)

    Waterfront

    My boyfriend and I went on this whale-watching tour together, and it became one of the most…read moreextraordinary experiences we've ever shared. We learned so much about whales, their behavior, and the marine environment, which made every sighting feel even more meaningful. We were especially fortunate because the whales were unusually active that day, and we even witnessed some rare sightings. Watching these magnificent animals move through the ocean was breathtaking, the kind of experience that makes time stand still for a moment. Beyond the excitement, the tour gave us such a beautiful and romantic day together. Being out on the water, learning, laughing, and witnessing something so remarkable side by side felt truly magical. We'll cherish these memories forever.

    This was a very informative and enjoyable experience. We booked the tour while the Tall Ships were…read morein town, which made it an especially fun time to be out on the water. The booking process was straightforward, and I received an email with clear instructions for check-in. The lines were super long because of the event, but we had allotted plenty of time, so it wasn't an issue. Once we were on the boat, we found seats inside and opened a window so we could enjoy the views and watch the many boats visiting the area. The commentator spoke throughout the tour and shared a wealth of interesting details and information. It was a great way to learn more while taking in the sights from the water.

    Boston Harbor City Cruises - Yelp elite event !!

    Boston Harbor City Cruises

    (15 reviews)

    Waterfront, South Boston

    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.

    Spirit of Boston Company, REVIEW: August 7, 2026 dinning…read moreexperience. I am writing to provide feedback regarding my recent dining experience on the cruise this past Friday. First, the table layout requires attention. Tables should not be placed near the entrances or exits, as this positioning lacks privacy and allows passing guests to crowd those dining. We requested a table change, and the floor manager promised to move us once a table became available, but she never followed up with us. Second, the food quality was disappointing. The steak was tough, and all of the food, including the steak, was served at room temperature. Additionally, the dinner rolls were cold, making it difficult to spread the butter without tearing the bread. Third, the service was severely delayed. Our waiter took our order but did not return with our drinks until I reminded him 20 minutes later. We could see our drinks sitting at the bar during this time. Overall, I would rate the service a 6 out of 10, and the food a 7 out of 10. On a positive note, the DJ was outstanding. The music selection appealed to everyone and created a wonderful, inclusive atmosphere where all the guests enjoyed dancing together. The entertainment easily deserves a rating of 10+. I hope this feedback helps improve the dining experience for future guests. Best regards,

    Classic Harbor Line Boston - tours - Updated October 2026

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