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Annapolis Power Boat Rentals and Charters: The Better Way

The concept of the Chesapeake Boating Club was founded in 1992 to provide flexible and affordable access to high quality and easy to use boats available on short notice and at a fraction of the cost you might anticipate for this much FUN! Becoming a member is a perfect way to get on the water and enjoy boating with minimal expense and hassle.

For a single annual fee you have access to our fleet of boats for your personal use, as well as Cruise/Rally events and lots of other Club Social events. Do you already own a smaller power boat?  Keep your smaller boat and use the Club for your big cruising boats as an alternative to two-boat ownership. Check out out fleet of great boats for the Chesapeake:

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Don't delay – memberships are limited to assure availability. The time to make sailing convenient, affordable and fun is now! Boats can be booked via our on-line Reservation System. Check out the 'Demo Account' to make yourself a "Member" and view a live calendar!

Most people today have other activities and family responsibilities that make owning a boat too daunting or unrealistic financially. Slip fees, insurance and normal maintenance alone can be more than $7500 per year and that does not include the purchase price of a new or used boat. How many people own a health club, golf course or bowling alley? Doesn't it make sense to consider a flexible boating program that allows you to do other things? So whether you're looking to get out for an afternoon with the gang on a fast and fun Twin Vee Power Catamaran or a long weekend getaway for the family aboard on the Club's Albin 36 Express Trawler, being a member of the Chesapeake Boating Club means our fleet is ready and waiting for you.

Join the Club!

Call (410) 280 8692

Club Member Testimonials

  • "... Ellen is by nature very cautious. Your concern over safety and the condition of the boat contributed to her enjoyment of the day. As I have mentioned, I think the sailing club is the greatest thing since sliced bread. A J/80 Fan!"

Discounts Available!

Graduates of the J/World Performance Sailing School qualify for special discounts when joining. Ask us about our current offer. Check out the Frequently Asked Questions section and photos of the entire fleet!

Free Get Acquainted Ride

Call us to schedule this "no pressure" test ride. It will give you a chance to check the boats first hand and it gives us a chance to assess your boating skills. Call the Club at 410.280.8692 to schedule an appointment. 

Check Out Rides

Every member must be checked out on each boat type and prove to be proficient, prior to being allowed to make a reservation. Additional training is available.