Annapolis Chesapeake Bay charters has never been easier. Contact us today and find yourself exploring the Chesapeak Bay from a charter boat today. Our charter boat experience on the Chesapeak Bay spans over 11 years and we have the fleet to match your level of experience and party size. We will help you select just the right boat for your next day rental or cruising vacation. To make your voyage as easy as possible, we can also assist you with itinerary planning, sailing instruction or provide a captain and crew – the choice is yours!