Chesapeake Windsail Cruises

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4160 Mears Ave Slp 15
Chesapeake Beach, MD 20732
Chesapeake Windsail Cruises is a beautiful way to enjoy all the splendors of the waters of the Chesapeake Bay, the Cliffs of Calvert or the beautiful environment of the region, all during a wonderful 2 ½ hour cruise on the Chesapeake Bay. . Chesapeake Windsail Cruises sails out of the beautiful Chesapeake Beach Resort & Spa located in the bay-side town of Chesapeake Beach, Maryland.

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5.05 reviews
Photo of Claire L.
Claire L.
8/30/2025

Stunning boat and great crew! We had a great time on the SV Eternal Hope with Captain Derek and first mate (and local expert) Nate. Highly recommend!!!

Bradley G.
9/5/2019

Outstanding experience on one of the cleanest and most beautiful sailboat I've ever been on. Top notch crew and service from start to finish. I highly recommend this group. My family had a great...

Tom A.
6/8/2018

First time my friend and I have ever sailed and we both loved it. I have some issues with mobility and the crew was very helpful in getting me on and off the boat. They we're very hospitable,...

Regina C.
5/15/2018

Excellent anniversary trip sailing with Capt Robert and Nate. Fun two hour trip with them laughing, eatinh snacks and enjoying the incredible weather. It was fun learning the sailing jargon and...

Jaclyn Y.
5/27/2018

Great sailing experience. We did the 3pm sail and it was beautiful. Perfect weather and we thoroughly enjoyed the people we were with. Highly recommend.

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