Chesapeake Boating Club Login

User Name:

Check Baltimore for

additional availability !

NOAA Forecastwindfinder

Club Login

Cruising Sailboats for the Chesapeake Bay

There's no better way to experience all the Cheapeake has to offer: cruising on a warm breeze with friends and family aboard the Club's J/32's,  J/105's, Beneteau 33 and Oday 28.  Being a member of the Club makes this dream a reality - and for far less money than charters or renting a sailboat.  Take a mini-vacation or an extended cruise with your family and friends using the Club's cruising sailboats.  You're boat is ready and waiting for you!

Sail Club Level 2 Annual Membership Includes Unlimited Use of:

  • (7) 26' J/80's
  • (5) 23' Sonar's
  • (4) Cal 22's
  • (3) Harbor 20's
  • (2) Ideal 18's
  • (4) 34' J/105's
  • (3) J/32's
  • (1) Beneteau 33
  • (1) Oday 28
  • Easy Online Boat Reservation System - Step Aboard and Go!
  • Two locations, Annapolis and Baltimore (check each location for current fleet)
  • No Maintenance, Repair or Dock Fees
  •    Check out the Membership Plans

The J/105 - Weekend Cruising on the Chesapeake

The J/105

Want to get away for a fun-filled weekend cruising on the Chesapeake Bay?  The Club's fleet of J/105 sailboats are ready and waiting for you.

A fun and forgiving performance boat that is easy to sail, J/105 offers low maintenance with a simple layout, has great performance, a large cockpit, predictable handling characteristics and makes no pretences of being a distance cruiser. The Club takes care of all the maitenance, so instead of varnishing toe-rails and troubleshooting systems you'll be enjoying a sail with friends.  

The J/32 - The Ideal Cruising Boat for the Chesapeake

Better than a Charter on the Chesapeake - The J/32 from the Club

When you're ready to go cruise one of the world's top sailing grounds - the Club makes it easy and economical with our fleet of J/32 sailboats - ready and waiting for you.  Pick your destination here on the Chesapeake, reserve your J/32 on the Club's web site, pack the cooler and head on down to the club to step aboard your J/32 and go cruising!  Being a member of the Club provides all the benefits of cruising the bay with none of the hassles and costs of owning, chartering or renting.  

The ideal cruising boat for many years has been the classic 40 foot sloop. For the first time, thanks to new building technology and design, the comfort and performance benefits of that cruising ideal are now available in 32 feet.   Apart from being more affordable to own and operate, there's an added dimension of comfort in a smaller boat: Maneuverability - landing at a dock or threading through crowded harbors. Furthermore, the J/32 is designed to sail well under mainsail alone and cruise with a small jib rather than genoa. There are no big sails to winch and wrestle and the constant sail changing of heavy displacement cruisers is avoided.

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.