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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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Classic Sail Boston
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markpR1200RK wrote a review May 2022
Rutland3 contributions3 helpful votes
The sailing trip was just perfect! Captain David is amiable and knowledgeable. I recommend Classic Sail Boston for anyone who wants a personalized experience.
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Date of experience: May 2022
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kimothy063 wrote a review Aug 2021
New York City, New York6 contributions9 helpful votes
My husband & I went with 2 other couples to celebrate our 8 year anniversary. Captain David & Hunter were fantastic. They were patient with us (a couple of our friends were late) and explained/answered all of our questions. The Captiva is a beautiful sailboat. I would absolutely recommend this trip. Next time we return, we're definitely doing a full day tour.
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Date of experience: July 2021
1 Helpful vote
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Tiffany K wrote a review Jun 2021
Boston, Massachusetts7 contributions5 helpful votes
+1
We had the best time today going out on Classic Sail Boston’s sailboat Captiva. I decided to book the charter for my husband and father-in-law for Father’s Day. As soon as we arrived on the boat, David immediately made us feel comfortable, gave us the history of the boat, and asked what we wanted to do during our charter. We had our 9 year old son with us. Dave included him in all aspects of manning the boat and answered his dozens of questions. Our son had the best time, and was super sad when our 4-hr charter ended. Overall, my entire family truly enjoyed the charter- truly a testament to Dave’s welcoming personality. We will definitely be booking again soon!
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Date of experience: June 2021
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Maya T wrote a review Jun 2021
6 contributions4 helpful votes
The sunset sail was incredible! Beautiful views of the Boston skyline and sailing around the harbor was perfect. Dave was a great captain and we all had a BLAST!
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Date of experience: June 2021
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LoveTravel213877 wrote a review Jun 2021
1 contribution1 helpful vote
private sunset sail 4daugther&5 friends-subsitute prom bc of COVID. David was amazing &they had a blast w/memorires 2last a life time.
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Date of experience: June 2021
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