Chesapeake Bareboat

Experience the freedom of a bareboat sailing charter with Chronic Sailing in the Chesapeake Bay, where you’re the captain of your own adventure. With no crew onboard, you’re in control, navigating your course through the Bay’s stunning waterways, past quaint coastal towns, scenic coves, and historic lighthouses. Our fleet of well-maintained vessels ensures a safe and enjoyable sail, whether you’re anchoring in peaceful seclusion or docking for a waterfront dinner. Perfect for seasoned sailors, this charter offers the ultimate blend of adventure, relaxation, and the unforgettable beauty of the Chesapeake Bay.