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.
Hours See website for hours.
Location
4160 Mears Ave, Dock A-Slip 15
Chesapeake Beach, MD
20732
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  • Group Tour Rates Offered
  • Group-Friendly
  • Student Group-Friendly
Rated 5 by Meredith W

July 16, 2026

Meredith W

Go sailing on the Bay with Derek and Jennifer!

I had a wonderful time sailing on the Bay just south of Deale. Derek the captain and Jennifer the mate were friendly, informative and attentive to safety. Jennifer educated me about the osprey we...

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Rated 5 by Clay E

June 29, 2026

Clay E

A wonderful cruise with wonderful people!

This was an excellent way to close out the month-long birthday celebration for my lovely wife. We were on this cruise with a couple celebrating their 1st anniversary, which made it even more...

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Rated 5 by TRACY F

July 04, 2024

TRACY F

Awesome Experience!

We had a great time sailing with Chesapeake Windsail. The crew was personable, considerate and friendly. First mate worked his butt off and he and the captain went out of their way to make it a...

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TripAdvisor Traveller Rating

Rated  based on 37 reviews
based on 37 Reviews
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