R&R Charters and Sail School

05/20/2026

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

02/02/2026

Florida IQC Dec 2-9, 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.

07/14/2025

A few more pictures from Greek adventure

07/14/2025

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