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Destinations on the Chesapeake

The Chesapeake Bay is the largest estuary in the United States and offers an enormous and varied cruising ground for sailors and power boaters alike. The Chesapeake Boating Club is located where the Severn river meets the Bay and is ideally situated for conveniently sailing or motoring to all the best the Chesapake has to offer. 

We've put together details on some of the most popular Chesapeake destinations to help make your adventure even more enjoyable. In the pages linked below we've included mileage, trip times, local amenities, and more. Pick the destination that interests you most and plan your next adventure with the Chesapeake Boating Club at J/Port. 

With over 2,500 square miles of water to explore, there's always somewhere to go, an event to attend, and something to see here on the Chesapeake. So whether you cruise to one of the highlighted destinations below or create your own cruise, it's time to stop dreaming and get out on the water with the Chesapeake Boating Club. 

Be sure to check out the latest destinations guide from Chesapeake Bay Magazine...

Join the Club!

Call (410) 280 8692

Club Member Testimonials

  • "In the last two years, I've sailed more than 40 days and only used about a quarter of my reserve days. With that experience, we plan to bareboat in the British Virgin Islands [ BVI ] in late fall.  The classes we took with the sailing school have helped to make our trips out on the bay more enjoyable and allowed us to plan on more adventures. I think if you total the cost of the BVI trip and J/Port it would still be less than if I owned my own 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.