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    Classic Harbor Line Boston

    4.7 (174 reviews)
    Open 10:00 am - 9:00 pm

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    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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    19 days ago

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    1 month ago

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    1 month 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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    1 year ago

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    2 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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    3 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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    4 months ago

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    2 months ago

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    2 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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    2 months ago

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    4 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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    3 months ago

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    9 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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    1 year ago

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

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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

    (467 reviews)

    Waterfront

    They offer a few different packages for this cruise. My family chose the 90-minute historic cruise…read morethat passed by many landmarks. I recommend getting there at least 20-30 minutes early to get in line so you can get a good seat. It's first come first serve. They had a bar inside serving basic drinks like beer, seltzers, sodas, etc. This experience was awesome! We got to see and learn a lot about Boston history. The sights were beautiful. It's definitely a fun activity to do if you're visiting.

    City Experience, I…read moream writing to provide feedback regarding our recent dining cruise experience. I attended the cruise with another church member who was considering booking a future event, but unfortunately, several operational issues negatively impacted our evening. First, the seating arrangement was poorly organized. Our table was placed too close to the exit, creating a bottleneck as guests went outside to take photos, despite ample open space on the other side of the room. We ultimately had to relocate the table ourselves. Second, there was a 20- to 30-minute delay in opening the buffet because the DJ failed to make the announcement. As a result, the food was cold by the time we served ourselves, despite being first in line. When we brought this to the manager's attention, she explained that the air conditioning cooled the food down. This explanation is concerning, as properly functioning warming pans should keep the food hot. Because of this, I lost my appetite, and my colleague was discouraged from planning her event on this vessel. Additionally, we believe the cruise should separate adult and family dining areas. Children were running around the buffet space, which posed a safety hazard given the potential for accidental burns from hot food equipment. Based on these factors, we rate the food a 1 out of 10 and the DJ a 6 out of 10. Despite these significant issues, the service we received from two of your staff members was exceptional. Our waitress, Ms. Fiona, demonstrated outstanding professionalism, compassion, and initiative. She frequently checked on us, apologized for the issues, and even brought us a well-done steak and dessert to ensure we had something to eat. Similarly, Ms. Dee went above and beyond her duties with her kindness and helpfulness to ensure we still enjoyed our evening. Both Ms.Fiona and Ms.Dee deserve a 10+ rating for their exemplary service. I hope this feedback helps improve future cruise operations. Best regards,

    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,

    City Cruises Boston Rowes Wharf

    City Cruises Boston Rowes Wharf

    (240 reviews)

    $$$$

    Waterfront

    Went on my first dinner cruise with my husband to celebrate our upcoming wedding anniversary and it…read morewas wonderful! Our server Jane was very nice and made sure we had everything we needed as our set meal choices were brought to us. The presentation of the food from the appetizers, entrees and desserts were well presented. We had the opportunity to explore the open view area of the ship to get some great pictures of the skyline and photos of us too. The staff around us were all friendly and had smiles too. As we left the two hour cruise they offered a treat to leave with (a cookie) but we were both full from everything we had already served us. I would definitely do this again.

    I did the whale watching excursion with city cruises and I had a great time. I went to the dock 15…read moremin before the board time and there was a very large line waiting to get on the boat. The boat itself was very big and had three levels. The inside of the boat felt a little on the older side, but I don't think that mattered much since I was outside looking at the water most of the trip. I found the people onboard incredible knowledgeable about the different species of whales and locating the whales. I was able to see multiple whales or see them jump out of the water multiple times. It was really exciting each time a whale was spotted and there was always a rush from one side of the boat to another when one was spotted. I didn't try any of the food onboard, but they had the typical snack foods.

    Classic Harbor Line Boston - tours - Updated September 2026

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