Chronic Sailing operates as more than a charter company. Based in Annapolis, they run a wide range of services that keep them on the water year-round, from sailing lessons and private charters to yacht deliveries, boat management, and seasonal maintenance. In the warmer months, their catamarans host everything from first-time sailors to long afternoons with friends on the Bay for Tunesday concerts. In the off-season, the focus shifts to deliveries up and down the Chesapeake and east coast, alongside repairs, preparation, and care for the boats in their fleet. Across it all, the throughline stays the same: sailing that feels accessible, unpretentious, and rooted in community rather than performance. Chronic’s approach leaves room for different kinds of sailors to find their place, whether that means learning the basics, trusting a crew with a delivery, or simply spending time on the water without needing a reason beyond being there.