The Captain and crew were excellent. Very accommodating and knowledgeable of all questions that were asked.





Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adirondack IV. Both sailboats are classically styled schooners and offer a smooth and gentle sailing experience as well as top-notch customer service by our captain and crew. Within minutes of leaving the dock, you'll forget the distractions of life on land, as you experience the ambiance of a sunset sailing cruise aboard a beautiful sailboat.
Sail around Boston's Seaport District and Harbor for 2 hours as you take in the sunset views of many newly constructed buildings along with some classic structures that originally comprised Boston's waterfront community.
Sail by Fan Pier and see the spanning Moakley Federal Courthouse, the World Trade Center and Harpoon Brewery.
Sail amongst the Inner Harbor Islands of Boston Harbor including Spectacle Island and Long Island with the Long Island Head Light House.
Sail by Castle Island, featuring Fort Independence and the Donald McKay Monument
The Captain and crew were excellent. Very accommodating and knowledgeable of all questions that were asked.
Sailing for the first time. I'm glad it was this company! Professional, and friendly! Thank you for best time amd experience!
I booked this at the last minute and was so glad I did. The crew was great, kind and knowledgeable. The weather was perfect and the view from the boat was extraordinary at sunset. It was so nice to be with a small group of people rather than a large boat.
Very organized and well planned sailing activity. All the crew was very attentive and nice. All my friends loved it
Beautiful weather and relaxing sailboat ride! Your view of the Boston skyline and the planes landing over the top of you at BOS is incredible!
This was such a. lovely sunset cruise in the harbor! Michael and his crew, Charlie and Kiara were very attentive and really seemed to love what they do. Highly recommend!
Absolute perfect sunset sail - crew was friendly and knowledgeable, made everything seem easy while still maintaining a strong sense of awareness and preparedness. The views were stunning and it was the Boston highlight of our family (of 7) trip.
Megan, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are elated to hear that the sunset sail was such a highlight of your family's Boston trip! It's wonderful to know you were well taken care of by the friendly crew, and we hope to have the pleasure of hosting you again soon! - Classic Harbor Line Boston
What a wonderful evening. Great views of the city. Fun experience with a great captain and crew. Very relaxing and enjoyable. We would do it again our next time to Boston. Couldn't recommend it more if you are looking for a fun beautiful way to spend an evening.
Must do if visiting Boston. One of the better ways to spend an evening on the water. I liked this better than the larger boats/ dinner cruises.
Nice and Quiet, drinks were on your honor at 6.00 a piece!! My husband got to have the wheel for a while (we are sailers). Very clean boat would definately go again