Sitting on Sail Boat

Meet the Captains

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 more than 30 years. Both have sailed in Greece, Italy, and the BVI.


Captain Penny currently holds a USCG Charter Captain's License, and is certified by the American Sailing Association to instruct:

  • Basic Keelboat (101)

Captain Dave holds a USCG Master's License and is certified by the American Sailing Association to teach:  

  • Basic Keelboat (101)

  • Basic Coastal Cruising (103)

  • Bareboat Chartering / Intermediate Coastal Cruising (104)

  • Coastal Navigation (105)

  • Advanced Coastal Cruising (106)

  • Ocean Passage Making (108)

  • Basic Celestial Navigation Endorsement (117)

  • Docking Endorsement (118)

  • Weather Endorsement (119)

  • Radar Endorsement (120)

  • Instructor Evaluator (211)

Captain Richard Myers got his first taste of sailing as a teenager, sailing a sunfish on the California coast, and later sailing windsurfers. He has been sailing his own boat, a 34' cruising sailboat, on the Chesapeake for 5 seasons now, and has experience sailing in the BVI, the Greek islands of the Ionian, and off the coast of British Columbia. He currently holds a USCG Captain’s License and is certified to teach the following ASA courses:

  • Basic Keelboat (101)

  • Basic Coastal Cruising (103)

  • Bareboat Cruising (104)

  • Coastal Navigation (105)

Captain Bill spent many years in the US Navy and has had the opportunity to sail in many different locations around the world. After many years in the corporate world, he has returned to the world of sailing. He currently is certified by the American Sailing Association to teach:  

  • Basic Keelboat (101)

Captain Rob Doolittle is an avid sailor. He owed a Hunter 280 which he has sailed on the Chesapeake Bay. More recently he purchase a Beneteau Oceanis 311 on berthed on the western Shore. He is a formed member of the CareFree Boat Club in Washington D.C. Besides the Chesapeake Bay, Rob has sailed in the BVI, Grenada and the Grenadines. As an American Sailing Association instructor he is certified to teach:  

  • Basic Keelboat (101)

  • Basic Cruising (103)

Start Sailing!

You know your current abilities - we know how to take you to the next level. Give us a call, and we'll be happy to go over the learning possibilities that would be the most beneficial. Together we'll mark the calendar for your great Chesapeake Bay sailing experience. We are proud to offer a 10% discount to our veterans on the ASA 101, 103, 104 and 106 classes! Thank you for your service!

The Boats

Moondance The beginning cruising level course is taught aboard our Hunter 28 in the Chester River, Prospect Bay, or Eastern Bay. At this level, you'll review and practice tacks and jibes while we all enjoy the fresh air and beautiful scenery. You will practice heaving to, reefing, and anchoring as well as learn to dock a vessel with an inboard engine. This three-day course is a great introduction to the cruising lifestyle.

At Last The intermediate and advanced cruising courses are taught aboard our Beneteau Oceanis 41 on Chesapeake Bay, Delaware Bay, and the Atlantic Ocean coast between the two bays. This learning experience is more advanced, and you'll learn to steer and plot courses, and to handle the larger boat while enjoying some of the best cruising destinations in the world. These classes are all live-aboard and last from 4 to 7 days depending upon the class level.

American Sailing Association


2010 ASA Sailing School of the Year

Contact Us

R & R Charters and Sail School
Captain David Renoll and Captain Penny Renoll - Owners / Instructors

Office Address:
R & R Charters and Sail School
428 Kent Narrows Way North
Grasonville, MD 21638

Mailing Address:
Captain David Renoll
On the Eastern Shore
231 Evelyne Street
Chester, MD 21619