Learn to sail today in the Chesapeake Bay area today! Looking for the perfect Annapolis activity? Chesapeake Bay boat rentals and lessons offers a beautiful fleet of sailboats for with our experienced captains providing all the essentials to get out on the water and see the historic waterways of the surrounding Annapolis area and nearby destinations. There’s never been more to do and see! Go for a half day, full day or as long as you like — your unique Annapolis and Chesapeake Bay area experience awaits! Contact us today and find yourself exploring the Annapolis Maryland and the Chesapeake Bay today and learn to sail today!