View of the Rainbow Dinghy Dock looking out onto the Chesapeake Bay. Photo courtesy of the author.

Back in 1959, Annapolis resident and sailor, Jerry Wood was in the toy business. But, he realized there were no facilities available in the area for the rental of boats, he opened Annapolis Boat Rentals in Eastport. His original facility was located at 6th Street on Back Creek. Jerry realized after a couple of seasons, that along with his rental operation he often needed to provide quick lessons so novices could become properly familiar with handling a sailboat.


Annapolis Sailing School Sign. Photo courtesy of the author.

The Rainbow 24

He saw an opportunity which ultimately became the first sailing school for adults in the U.S. and aptly named it; Annapolis Sailing School. Being in the toy business, Jerry also had accessibility to plastic manufacturers. This connection initiated the construction of the Rainbow 24, designed by Sparkman & Stephens. The Rainbow 24 was specifically created to teach beginning sailors the hands-on Annapolis Way” of sailing. This new sloop, safe and un-capsizable; still remains the go-to vessel  for new sailors to learn the skills and enjoyment of sailing.


1962 article about the new sloop style, the Rainbow; created by Annapolis Sailing School. Photo courtesy of John Cosby of Annapolis Sailing School.

Since 1962, the Annapolis Sailing School has been located at its present place of business on a waterfront parcel at the end of Bembe Beach Road. It fronts on the mouth of beautiful Back Creek. This breathtaking peninsula complete with beach areas and gorgeous views, meets the beautiful expanse of the Severn River near the Chesapeake Bay. Along with the surrounding properties, the land was once owned by Gustav F. Bembe who later divided it into parcels to be sold.  

 Annapolis Sailboat Show

Jerry Wood and three partners were also the creators of what is now the United States Sailboat Show. At the start in 1970, floating plastic docks that Jerry designed for the sailing school were towed over to City Dock and used to display boats at the Show. It was the first time so many boats had been viewed and accessed in the water by potential buyers and avid boaters. This popular annual event soon expanded to include another weekend for the Power Boat Show. These shows are traditionally held back to back during long weekends in October.


A view from Annapolis Sailing school across Back Creek. Photo courtesy of the author.

Teaching people to sail grew in popularity at the Sailing School in the 1980s, when there were as many as 120 students each weekend. Their two-day course emphasizes learning to sail in a fun, safe, and simple way. Instruction includes classroom theory, as well as hands-on time with a low teacher-to-student ratio and certification can be obtained as per the requirements of the American Sailing Association. It's no wonder why so many novice sailors from across the country have been attracted to this popular sailing school on the Bay.


Annapolis Sailing School. Photo courtesy of the author.

Annapolis Sailing School Today

After the passing of Jerry and Kathy Wood, the school was purchased by Timothy Dowling in 2007. Then again it changed ownership in 2014 to Rick and Jenny Nelson. The Nelsons were very familiar with the school and property over the years. In fact, Jenny had worked as an instructor at the school.   

Presently, there are approximately 35 pupils taking the weekend course and they offer Youth Sailing as well as Family Sailing Classes. Students learn quickly and spend most of the time putting those lessons into action by navigating the waters of Annapolis and the Bay. Annapolis Sailing School also offers a Keelboat Club, Power Boat School as well as outdoor Yoga classes, run by Blue Lotus Yoga; on their sandy shores.

This time last year, the Annapolis Sailing School celebrated its 60th anniversary with a renovation of the facility including additions and improvements, an updated fleet of boats, and new event space! General manager John Cosby, who has been with the business since 1977, is proud that the mission of the sailing school remains the same - to prepare as many folks as possible to safely enjoy the fun and wonders of sailing on the shores of the Chesapeake Bay.

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