David K.
6/23/2025
This was probably one of the best days I can remember. If you are just contemplating doing this, do this! You will not regret it! And use this company, family owned and operated with someone who...
Classic Sail Boston
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(59)
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142 Seaport Blvd
Boston, MA 02210
Classic Sail Boston offers private sailing charters in Boston Harbor aboard a 45' Classic Wooden Sailboat. Guests can enjoy a 2-hour private charter exploring the inner harbor, passing by iconic landmarks such as Seaport, Southie, Castle Island, and more, while learning about the history of these locations or simply relaxing to music.
For those seeking a longer adventure, the company also provides 4-hour half-day private charters to Boston Harbor Islands or full-day private charters for a comprehensive exploration of both inner and outer harbor areas. Guests are encouraged to bring their own snacks, drinks, and enjoy activities like swimming, island hopping, and close-up views of lighthouses during the extended tours.
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Reviews
5.059 reviews
Amber B.
5/9/2025
What a great experience! We sailed with Captain David on a beautiful day in early May. Because my partner has such a strong desire to learn to sail, he asked a lot of questions to learn about the...
Mike T.
8/10/2025
Spent the morning and early afternoon with David on a private charter with my wife for my birthday. Though the wind was light the experience was full and informative. The Skip Jack is awesome and...
Greg W.
8/7/2022
Captain Dave is the kind of guy that not only oozes knowledge of sailing, the route, and surroundings on your trip, but he also fit into to group seamlessly and doesn't feel like an outsider......
Michael B.
8/10/2024
Not sure what to say but the boat ride was good enough, small and quaint the owner and deck crew were nice.
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