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Classic Sail Boston

Boston, MA, USA
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About Classic Sail Boston
We offer private sail charters and tours of Boston Harbor and Boston Outer Harbor Islands aboard a classic wooden Chesapeake Skipjack sailboat. 2,4, and 8 hour private charter cruises are available. Pick-up/Drop-off locations available throughout Boston Harbor: Charlestown, East Boston, Seaport District/Downtown Boston. BYOB or let us Cater.
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Hours Today: 9:00 AM - 9:00 PM
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Anup G wrote a review Jul 7
Birmingham, Alabama1 contribution
Was a great day on the water. Showed us the sights in and around Boston and was very informative. Even had one member of our group help out with getting the sail up and down which was so cool !! Highly recommend !
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Date of experience: July 2020
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Kristin Z wrote a review Jun 2020
Wellesley, Massachusetts2 contributions
I booked this trip as a special Father’s Day outing for our family and it was amazing. We’ve lived in Boston for 6 months and this has been our favorite way to see the city. Dave was an excellent guide and made it fun for all of us. From letting my husband hoist the sail,
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Date of experience: June 2020
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Response from David P, Owner at Classic Sail Boston
Responded 2 weeks ago
Kristin, thank you so much for your kind words. Families like yours and evenings like that are why we do what we do. Look forward to seeing you all again!
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Lisa S wrote a review Jun 2020
2 contributions
Perfect Day. We were celebrating Father's Day with our adult children. The weather was beautiful and we had some wind. David is a perfect host. He will give you what you want. We are interested in all things. We had four hours. He can provided you everything you want to
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Date of experience: June 2020
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Response from David P, Owner at Classic Sail Boston
Responded 2 weeks ago
Thank you so much Lisa! It was my pleasure having you and your family for such a pleasant sail. Enjoy the rest of your summer and hope to see you again!
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Michael M wrote a review Aug 2019
Atlanta, Georgia14 contributions2 helpful votes
Thank you David and Classic Sail Boston for providing us with the perfect day for my wife's birthday. An amazing experience. David was at the meeting spot ready for us, he took us on an amazing 4 hour sale to the harbor islands and then to the inner harbor. He entertained us
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Date of experience: August 2019
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Response from David P, Owner at Classic Sail Boston
Responded Aug 28, 2019
Micheal, Thank you so much for taking the time to leave such a nice review. It's my honor to be entrusted with your special occasion and having you and your wife aboard for such a beautiful sail was my pleasure. Fair Winds,
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TXnave wrote a review Aug 2019
Fort Worth, Texas19 contributions1 helpful vote
+1
Captain David was very knowledgeable and friendly during our family sunset sail. Most memorable experience in New England by far!
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Date of experience: August 2019
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