About Us

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 almost 50 years. Both have sailed in Greece, Italy, the BVI, Bahamas, Bermuda, and the ICW to Florida.

Captain Penny has cruised on the Chesapeake Bay, the Caribbean, the Med, the Bahamas, Bermuda, and down the east coast to Florida. She currently holds a USCG Charter Captain’s License, and is certified by the American Sailing to instruct:

  • Keelboat 1 (201)
  • Basic Power Boat (201)

Captain Dave ASA Senior Master Instructor has sail on the Chesapeake Bay for more than 40. He has cruised in the Caribbean, the Med, the Bahamas, up and down the east coast of the US, and Bermuda. He and his wife Penny sail to Florida every few years. He currently holds a USCG Master’s License and is certified by the American Sailing to teach:  

  • Keelboat 1 (201)
  • Keelboat 2 (202)
  • Coastal Cruising (203)
  • Bare Boat Chartering (204)
  • Coastal Navigation (205)
  • Advanced Coastal Cruising (206)
  • Ocean Passage Making (208)
  • Celestial Navigation (207)
  • Catamaran (214)
  • Dinghy and Outboard Endorsement (216)
  • Basic Celestial Navigation Endorsement(217)
  • Docking Endorsement (218)
  • Weather Endorsement (219)
  • Radar Endorsement (220)
  • Master Instructor ( 211)
  • Senior Master Instructor (222)
  • Basic Power Boat (201)
  • Cruising Power Boat ( 203)
  • Advanced Power Boat ( 204)
  • AB Master Insgtructor (211)
  • AB Senior Master Instructor (222)

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 holds a USCG Master Licenses and currently is certified by the American Sailing Association to teach:  

  • Keelboat 1 (201)
  • Keelboat 2 (202)
  • Coastal Cruising (203)
  • Bare Boat Cruising (204)
  • Coastal Navigation (205)
  • Advanced Coastal Cruising (206)
  • Dinghy and Outboard Endorsement (216)
  • Docking Endorsement (218)
  • Master Instructor (211)

Captain Marty retired from the US Navy and recently retired after many years in the corporate world. He has now embarked on his third career, sailing. He annually charters a sailboat to travel throughout the Caribbean. He sailed Barnegat Bay, NJ for 8 years, then purchased a 27′ sailboat and sailed the Delaware River and Chesapeake Bay for 10 years. Captain Marty has since upgraded to a 38′ sailboat and is moving to Kent Island, where he intends to spend more time on the water, enjoying sailing and family time. He is a licensed USCG Captain and is certified by the American Sailing Association to teach:  

  • Keelboat 1 (201)
  • Keelboat 2 (202)
  • Coastal Cruising (203)
  • Bare Boat Cruising (204)
  • Marine Weather ( 219)

Captain Truc Duc just started sailing in the summer of 2020 by taking sailing lessons from R&R, but got hooked on the lifestyle immediately. The lifestyle must have embraced him as well, since a lucky breeze brought him his own 40′ sailboat this past fall. He plans to go as far as his imagination and seamanship will take him with dreams of one day sailing to Antarctica. He currently holds a USCG license. He is certified by the to teach:  

  • Keelboat 1 (201)
  • Coastal Cruising (203)
  • Bare Boat Cruising (204)

Laura Olsen is the proud captain of her own sailing vessel and has sailed many years on the Chesapeake Bay.  She has completed all the student level classes from 101 – Keelboat 1 to 108 – Offshore Passage Making.  She is a charter captain on the South River and has made passages from Norfolk to Bermuda, Marsh Harbor, Bahamas to St. Augustine, FL and Bermuda to New York City.  She is a member of the Chesapeake Area professional Captains Association and currently holds a USCG Master license with sailing and towing endorsements. She is certified to teach:

  • Keelboat 1 (201)
  • Keelboat 2 (202)
  • Coastal Cruising (203)
  • Bare Boat Cruising (204)
  • Docking Endorsement (218)

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, 102, 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.

Cool Change – The Coastal Cruising and Bareboat Cruising level courses may be taught aboard our Beneteau 321 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, Coastal Cruising class 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. The four-day Bareboat Cruising class will show you the joy of multi-day cruising on the bay. The 7-day Advance Coastal Cruising class gives you the experience of an extended cruise with lots of night navigation. This may include a Delmarva circumnavigation depending upon the weather conditions and the class size. Finally, the Offshore Passage Making class (12-14 days) provides the student with an ocean passage, depending upon the weather forecast, a cruise to Bermuda, Newport, RI, or Beaufort, NC. These classes are all live-aboard and last from 4 to 14 days depending upon the class level.

Contact Us

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

Marina Address:R & R Charters and Sail School
301 Tackle Circle
Chester, MD 21619
Phone:570-690-3645

Mailing Address:Captain David Renoll
107 Lexington Road
York, PA 17403
Email:randrchartersandsailschool@gmall.com