The Adirondack II was gorgeous, the masts alone were more beautiful than most hardwood furniture, and the prices from tickets to refreshments were reasonable. Most importantly, the captain and crew were extremely friendly, wonderful to talk to, and make one want to visit again!
If I had to find a complaint, it would only be that they don’t sell merch, because the crew had some pretty slick hats and vests, which I’d certainly have bought, were they available! 10/10 will sail again.
June 2026
We had a great time making with Classic Harbor Line on one of their Adirondack Schooners. Captain Eric K. and the crew, Claire and Kira, were all lovely and very welcoming. Special shout-out to Kira who was literally as nice and friendly as a person could possibly be, and spent time getting to know everyone on board. We spent about an hour and a half sailing around Boston's inner harbor, got some excellent views of the skyline and planes landing at Logan airport (often almost right overhead!) and in general relaxing and enjoying being on the water. It was my favorite activity that we did in Boston this trip.
My family really enjoyed our sail with Classic Harbor Line. Kira and Claire were fantastic. Their knowledge of the area was amazing and watching their skill with sailing was very impressive. Everyone was very nice and helpful.
The Adirondack II was gorgeous, the masts alone were more beautiful than most hardwood furniture, and the prices from tickets to refreshments were reasonable. Most importantly, the captain and crew were extremely friendly, wonderful to talk to, and make one want to visit again! If I had to find a complaint, it would only be that they don’t sell merch, because the crew had some pretty slick hats and vests, which I’d certainly have bought, were they available! 10/10 will sail again.
We had a great time making with Classic Harbor Line on one of their Adirondack Schooners. Captain Eric K. and the crew, Claire and Kira, were all lovely and very welcoming. Special shout-out to Kira who was literally as nice and friendly as a person could possibly be, and spent time getting to know everyone on board. We spent about an hour and a half sailing around Boston's inner harbor, got some excellent views of the skyline and planes landing at Logan airport (often almost right overhead!) and in general relaxing and enjoying being on the water. It was my favorite activity that we did in Boston this trip.
Our original booking got cancelled... read full review
My family really enjoyed our sail with Classic Harbor Line. Kira and Claire were fantastic. Their knowledge of the area was amazing and watching their skill with sailing was very impressive. Everyone was very nice and helpful.