About Us


Boating should be flexible, fun and affordable! This is what we believed when we opened for business in 1992 in the Historic Eastport section of Annapolis, and that commitment has made us what we are today – The #1 flexible boat sharing program on the Chesapeake Bay. Let us help you experience the thrill of boating at a fraction of the cost of ownership.

We have a wide variety of boats – both sail and power. The possibilities are endless; so whether you want to go day sailing, cruising by power or sail for a weekend, or even plan a week-long excursion: the Chesapeake Boating Club is the affordable, no-hassle way to get out boating.

Stop dreaming and start boating – Sail, Power, and Instruction: Chesapeake Boating Club has it all!

Are you dreaming of the day when you will find the perfect boat, arrange for a place to keep it, discover the energy to care for it, and have enough time left to actually use it? Stop dreaming and get out on the water with the Chesapeake Boating Club.

The Club offers you a large variety of boats available on short notice and at a fraction of the cost of boat ownership or charters. Becoming a member of the club is the perfect way to get out on the water and enjoy the Chesapeake Bay with minimal expense, hassle and maximum amount of fun.

Whether you are looking for a lazy afternoon day-sail, a comfortable harbor cruise with the family, or an extended getaway cruise, the Chesapeake Boating Club has you covered. Your fleet is awaiting your arrival, just minutes away from where the Severn River meets the Chesapeake Bay.

Which option interests you more – power or sail?  Or perhaps both?  Either way, we have the flexible, affordable, and hassle-free way for you to get out on the water today!