Sitting on Sail Boat


2010 ASA Sailing School of the Year

Learn to Sail...and enjoy a little R&R!

R&R Charters and Sail School is owned and operated by Dave and Penny Renoll, who both hold USCG licenses and have been sailing on the Chesapeake Bay for 30+ years.  They have also sailed in Greece, Italy, and the BVI.  “It’s fun, it’s an adventure, and it’s a wonderful way of life!”

The Learning Experience

We are professional educators who delight in sharing our passion for sailing. Each student will enjoy a personal learning experience, as they master the knowledge and skills to feel confident in their sailing abilities.

Advance your skills with some individual instruction, or learn as a small group with friends and family. Our maximum of four students per boat gives all students the greatest amount of boat handling experience on the water.

Captain Penny always says: "Learn to sail; you might want to go somewhere."

© video by Ti Zhang, 2020

ASA Veterans Program

R&R Charters and Sail School is pleased to offer a 10% discount to our veterans for ASA 101, 103, 104, & 106 on the water classes. Thank you for your service to our country!