R&R Charters and Sail School
Grasonville, Maryland
| (570) 690-3645 | randrchartersandsailschool.net

Our school is located on the Eastern Shore of Maryland, easy to drive to with traveling through major urban areas. Around our marina are excellent restaurants without walking distance as well as many more within a short drive.

We own two boats, Moondance, a Hunter 28, and At Last, a new Beneteau Oceanis 41 for our 104 and 106 classes. Our beginning courses are taught over three days in the peaceful Chester River and Prospect Bay just off the Chesapeake Bay. For our 104 class we explore the calm rural anchorage areas of the Eastern Shore and also a visit Annapolis. Our 106 class does a Delmarva circumnavigation of approximately 450-500 nm with lots of night and ocean sailing experience or an extended cruise down the Chesapeake Bay also with lots of night sailing experience. For our 108 course, we will cruise to Block Island, RI, an ocean passage of approximately 300 nm.

All instructors hold USCG licenses and are ASA certified. All are avid sailors and own boats. They have over 100 years of combined sailing experience, not only on the Bay, New England, and along the east and west coast but also in various locations around the world such as the Caribbean, the Med, and the South Pacific.

We ensure that all students receive the personalized instruction for every course. Because we limit the size of our on the water classes to a maximum of 4 students, all have lots of opportunity to handle the boat in all aspects. Our 101 & 103 classes are three days so that students truly have the opportunity to master the material and skills. The 104 class is a true 4 day cruise during which the students experience provisioning and on board food preparation, planning the daily routes, and doing all the navigation drills, thus mastering skills for their own bareboat charter anywhere in the world. The 106 class provides a great long distance cruising experience prior to doing a major ocean passage. And finally, our 108 class provides students with their first ocean passage experiencing an extended watch system and practicing their celestial navigation skills learned in the 107 class. All our classroom courses are completed in a formal classroom under the guidance of a certified instructor – no at home study during which students become frustrated and confused and normally give up before completing the material.

American Sailing Certifications Offered

101, 103, 104, 105, 106, 107, 108, 117, 118, 119, 120

Other Services Available

Corporate Team Building Courses, ASA 'Challenges', Day Sail Charters (public), Day Sail Charters (member-only), Vacation Charters, Sunset Cruises,


ASA Veterans Sailing Education Program - Sign Up Now >>

At ASA we recognize the sacrifices made by the brave men and women who have served or are serving in our country's armed forces. As a token of our appreciation, and our way of saying thank you, we are inviting veterans and active military personnel to share our passion for sailing by offering a discount on our ASA 101 Basic Keelboat Sailing course. R&R Charters and Sail School is offering a minimum of $50.00 or 10% off their ASA 101 Basic Keelboat Sailing course.

Contact Information

R&R Charters and Sail School

Address 428 Kent Narrows Way North GrasonvilleMD21638United States
Phone (570) 690-3645
Website randrchartersandsailschool.net
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