Chesapeake Windsail Cruises

This cruise sails out into the Chesapeake Bay, possible sightings dolphins, ospreys and other amazing habitats or cruise ships in the shipping canal. Enjoy the peaceful sound of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay.


See website for hours.


4160 Mears Ave, Dock A-Slip 15
Chesapeake Beach, MD
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  • Group Tour Rates Offered
  • Group-Friendly
  • Student Group-Friendly
Rated 5 by L7153PLaprilp

June 21, 2021


Best Day Cruise Ever

Captain Ken and his First Mate Dylan were the absolute best! They were very knowledgeable and friendly which made for a great experience. 10/10 I definitely would recommend!

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Rated 5 by caviw2021

June 17, 2021



Nate and Priscilla were very warm and welcoming. We felt safe the entire time. The ride was amazing, the day was perfect. Looking forward to a sunset cruise :) 2.5 hours were ample. Thank you 😎

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Rated 5 by dskaddan

June 03, 2021


Great sailing experience

The 2 1/2 hour charter departs from the Chesapeake Beach harbor. Parking readily available. ~40 foot sailboat, spotless clean and in great shape. First mate Nate is competent, friendly, attentive and...

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TripAdvisor Traveller Rating

Rated  based on 15 reviews
based on 15 Reviews
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