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 Jpell64

September 18, 2026

Jpell64

Relaxing Afternoon

Noon cruise was lovely. Jennifer and Bob were excellent hosts and ship mates. Weather was beautiful. My friend and I even got to drive.

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Rated 5 by Chris L

September 08, 2026

Chris L

Beautiful day for sailing!

We took the 3pm Sailboat Cruise on Sunday September 6th. The weather was amazing for sailing and the Captain (Rob) and First Mate (Jennifer) were so professional, knowledgeable and fun. They said...

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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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TripAdvisor Traveller Rating

Rated  based on 39 reviews
based on 39 Reviews
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