R&R Charters and Sail School

R&R Charters and Sail School We are an ASA sailing school and teach beginning sailng through advance sailing. We also offer the docking endorsement course.

We offer American Sailing class from basic keelboat through advance coastal cruising. In add, we offer the following classroom courses: coastal navigation, basic celestial navigation, celestial navigation, marina weather, and marine radar.

05/20/2026
Come join R&R Charters and Sail School sailing on the Chesapeake Bay.  We offer classes at all levels!
05/06/2026

Come join R&R Charters and Sail School sailing on the Chesapeake Bay. We offer classes at all levels!

03/12/2026
Florida IQC Dec 2-9, 2025
02/02/2026

Florida IQC Dec 2-9, 2025

Arabella from Bermuda to St. Thomas Ded 9-14, 2025
02/02/2026

Arabella from Bermuda to St. Thomas Ded 9-14, 2025

11/29/2025

Here is an opportunity for sailors to join a cruise on the Chesapeake Bay in 2026. Check or website for options and registration.

Chesapeake Bay Flotilla
May 2 - Day #1 – Meet and board your vessel by 1600 – Welcome Party and Orientation
May 3 - Day #2 – Depart at 0900 heading for St. Michaels. Arrive by 1500. Overnight Docking at the Maritime Museum. Dinner at 1800 on shore at The Crab Claw Restaurant
May 4 - Day #3 – Depart at 0900 heading to Oxford. Overnight docking Safe Harbor Oxford. Arrive by 1500. Dinner at a local restaurant at 1800.
May 5 - Day #4 – Depart at 0900 heading to Solomon’s Island. Arrive by 1600. Overnight docking at Safe Harbor Zimmermans. Dinner at La Vela Restaurant at 1800.
May 6 - Day #5 – Depart at 0800 heading to Rhode River. Arrive by 1600. Overnight raft up Happy Hour on board At Last 1700. BYOB and a hors d’oeuvres to share. Dinner on board your own vessel. Be sure to be prepared with necessary provisions.
May 7 - Day #6 – Depart at 0900 for Annapolis. Arrive by 1400. Overnight mooring. Happy Hour on board At Last at 1700. BYOB and a hors d’oeuvres to share. Dinner on shore or on your own boat.
May 8 - Day #7- Depart by 0900 for Castle Marina. Arrive by 1500. Top off fuel and pump out. Top off water tanks and spray down boat. Final cocktail party on board At Last at 1700.
May9 – Disembark from boats and head home. Safe travels.

A few more pictures from Greek adventure
07/14/2025

A few more pictures from Greek adventure

Here are some of our pictures from our Greek flotilla.  Enjoy!
07/14/2025

Here are some of our pictures from our Greek flotilla. Enjoy!

Address

301 Tackle Drive
Chester, MD
21619

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 9pm
Thursday 9am - 5pm
Friday 9am - 5pm
Saturday 9am - 5pm

Alerts

Be the first to know and let us send you an email when R&R Charters and Sail School posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to R&R Charters and Sail School:

Share