We are a charter sailing business operating in the Annapolis, Md area out of the Magothy River. We offer sailing trips on our 26' trimaran, "Dragonfly". It is a unique and exhilarating boat offering speed and excitement while sailing with minimal heel, providing stability and comfort for our passengers.  Depending on your wishes, we can sail in the protected waters of the Magothy River, or head out into the Chesapeake Bay!

We love nothing more than showing our guests the beauty of the Chesapeake Bay and Annapolis areas, combined with the thrill of sailing a high performance trimaran. This is a great time to get out on the water, relax, and enjoy the beautiful scenery.

​Recently, Chesapeake Sailing Tours was featured in  Baltimore Magazine and The Washingtonian as a great way to get out, and experience the Bay. Please check out the articles here, and here!

If you have any questions, please don't hesitate to call or to send us an email. Whether you are interested in a daysail or a sunset sail, we will do what we can to meet your needs. We look forward to taking you sailing on the Chesapeake Bay! 
Tour Options
About Us
Contact Us


Chesapeake Sailing Tours
Tell a friend about this page
      Come sailing with us on The Chesapeake Bay!
Ask us about purchasing gift certificates!