KeelBoat Club

KeelBoat Club

The KeelBoat Club was originally started as a sailing club to give our students ongoing access to our fleet of Rainbow 24’s.  Over the years, the sailing club has evolved with Monday Night Rainbow Races, Social Events, Wednesday Night Racing on our Caraluna 245 by Tartan, Winter Seminars, a Clubhouse, Beach and Paddleboard Use, access to dinghies, and Ultimate level overnight cruising on our Saber 34 and Newport 30.  Make sure to check out the benefits sheet for all the benefits and pricing of our sailing club.

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Club Details

Level One – The Social Sailor

The Social Sailor membership is a great way to get involved in the sailing community at the Annapolis Sailing School. This membership gives you access to invitation-only events such as our Monday night regatta series, beach cookouts, the Blue Angels flight demonstration, a Fourth of July party (with a spectacular fireworks view), and boating seminars.

In addition, we will help you connect and network with other sailors by adding you to our member-matching Facebook group, where members from all KeelBoat Club levels can coordinate sailing events, post questions, and learn about exclusive offers at the school.

To top it all off, you will receive a 10% discount on any course you take with the school and 10% off rentals. For a complete list of benefits see the chart here.

Level Two – The Rainbow Sailor

The Rainbow Sailor membership gives you access to the Annapolis Sailing School as the ultimate summer hangout. Get on the water with a generous allotment of reservations on our Rainbow 24 daysailers, and access to our Bembe Beach and Back Creek Beach and our waterfront clubhouse – the Sail Shed. Add to it the unlimited use of our paddleboards and kayaks, and you have even more ways to have fun on the Bay this summer. You can also book one free, two-hour private instruction to refresh or advance your sailing knowledge.

Level Three – The Ultimate Sailor

The Ultimate membership enables you to take sailing to the next level. With all of the benefits of the Social and Rainbow levels, the Ultimate Sailor is your “All Access” pass to the Annapolis Sailing School. We have fully outfitted cruising sailboats for day or overnight sailing, accessible only to our Ultimate level members. To ensure the ultimate in access and service, this level is limited to 12 members.


For more information please call 410.267.7205 or email

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