Welcome
Aboard!
Sailing Adventure
Chesapeake Skipjack Charters is Kent Island’s only Skipjack Touring Company, designed for family and small group 2-3 hour sailing adventures for morning, afternoon, and sunset cruises. We are a family-owned and operated charter company that offers tours on the Chesapeake Bay aboard the Skipjack Lady Helen, which is the Maryland state boat.
The thrill of sailing
This is not your average sailboat ride, it’s a step into history.
When you set foot on the Skipjack Lady Helen you can see her beautiful wooden features, hand-painted name trail-boards, huge sail, and taste that salt spray, much like sailors from years before. These features are part of the thrill of sailing. And when we hoist the sails and step back in time, you’ll have an experience you’ll be talking about for years to come.
Sail your day away aboard the Skipjack Lady Helen and celebrate the joys of life and special occasions in a unique and tranquil setting. We offer trips to local sights and sail where the wind takes us as you leave the burdens of life at the dock. Trips depart from Stevensville, located across the Bay Bridge from Annapolis Maryland.
Captain Jeff is happy to have you aboard and ready to share the Chesapeake Bay with you where the wind takes him.
First Mate Janet is married to Captain Jeff and is an artist and Art Teacher in Maryland. She is typically found hoisting sails, assisting guests, and being a great First Mate.
First Dog Roxy Sunshine can sometimes be found sleeping on the job.
