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Sail Boat Charters | Chesapeake Bay - There's a Better Way

Take the Helm with a membership to the Chesapeake Boating Club

The concept of the Chesapeake Boating Club was founded in 1992 to provide flexible and affordable access to high quality and easy to sail 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 sailing 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 racing opportunities (as skipper or crew), Cruise/Rally events, Frostbite Racing (November-March), and lots of other Club Social events. Do you already own a J/22 or J/24? Keep on racing your smaller J, and use the Club for your big cruising boats, as an alternative to two-boat ownership. Check out our fleet:

day_sailers_green cruising_sailboats_green

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.  Consider the costs of owning:

  • Slip Fees - $$$
  • Insurance - $
  • Boat Maintenance - $$
These costs easily add up to $7,500 per year and don't even include the purchase price of a new or used boat. As our members say: "The Club is a no-brainer!"

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 J/80, a long weekend getaway for two on a J/105 or the vacation cruise for up 2 weeks exploring the Chesapeake, being a member of the Chesapeake Boating Club means our fleet is ready and waiting for you.

Sail Club Gallery

Join the Club!

Call (410) 280 8692

Club Member Testimonials

  • "Had to pack a few personal things, get some ice, buy a few groceries and take off on a 3 day adventure less than an hour after stepping foot aboard. That's what a sailing time share is all about: for busy folks who don't have the time to own their own boat but love to sail a good boat."

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.