Chesapeake bay sailing in Chester, Maryland

R&R Charters and Sail School, located in Chester, Maryland, United States, is a professional institution dedicated to sharing the joy of sailing with students. Our experienced educators provide personalized instruction to help students master the knowledge and skills needed to feel confident on the water. Whether you prefer individual instruction or learning in a small group setting with friends and family, our maximum of four students per boat ensures that each student receives ample hands-on experience. Captain Penny encourages students to "Learn to sail; you might want to go somewhere."

Ohana Charters is a travel agency located at 500 Piney Narrows Road in Chester, Maryland, United States. Specializing in Annapolis Charter, Catamaran Charter, Sailing Charter, and more, Ohana offers a luxurious and unique sailing experience on the Chesapeake Bay. Guests can enjoy stunning sunsets, delicious food, and the opportunity to enhance their sailing skills. Whether celebrating a special occasion like an anniversary, birthday, or graduation, or simply looking for a relaxing getaway, Ohana Charters provides a memorable and unforgettable experience on the water. With the option for overnight stays, intimate family reunions, or exclusive events, Ohana Charters offers a variety of packages to suit every need. Experience romance, relaxation, and adventure aboard Ohana Charters for an unparalleled sailing experience.