• Welcome
  • Chesapeake Boating Club
  • Sail Club
    • J/Port Fleet
    • FAQ
    • Harbor 20's - New!
  • Power Club
  • News & Events
  • Site Map
  • Contact
Club Login Boating Club Test Account Login Chesapeake Boating Club Cruising Destinations Club Member Testimonials Weather Forecast for Annapolis New! Harbor 20 Harbor 20 J80 Sailboat J80 J32 Sailboat J105 J105 Sailboat J105

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 $10,000 per year and that doesn’t 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 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.

The concept of the Chesapeake Boating Club was founded in 1992 to provide flexible and affordable access to high quality and easy to sail J/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.

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 FlexBoat Reservation System. Check out the 'Demo Account' to make yourself a “Member” and view a live calendar!

MEMBERSHIP IS LIMITED: As more boats are added to our fleet, more memberships become available. Our ratio is 10 members per boat figured on a yearly average. All memberships are valid for one (1) year from contract date.

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.

CHECK OUT RIDE: 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.

DISCOUNTS: 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!

The Chesapeake Boating Club is the ideal solution for sailors looking for a flexible and affordable way to get out on the water at a fraction of the cost of boat ownership or charters. Our fleet of fourteen sailboats from 26 to 34 feet offers a variety of sailing possibilities to satisfy even the most active sailors.

The Affordable Alternative to Boat Ownership

  • Welcome  
  • Sail Club  

Chesapeake Boating Club at J/Port     410.280.8692     213 Eastern Avenue, Annapolis, Maryland 21403    Contact Us