Chronic Sailing offers curated private and multiday sailing charters based in Annapolis, Maryland, and specialized waterfront experiences across the Chesapeake Bay and beyond. The company operates a fleet that includes a Dufor 470, an Oceanis 45 and multiple luxury catamarans, and provides flexible private charters, bareboat options, and themed multiday itineraries like Slowdown, Dos Milagros, and Starz. Trips span half-day, three-quarter-day, full-day, and multiday formats, plus sunset sails of three, six, and eight hours, making options suitable for romantic evenings, corporate outings, family celebrations, and skill-building cruises.
Chronic Sailing combines professional captains and custom itineraries to prioritize safety, comfort, and memorable on-water moments. The fleet’s open-concept catamarans emphasize spacious deck areas and seamless interior-exterior flow for relaxed socializing and scenic viewing. Guests can expect departures from Annapolis for Chesapeake Bay adventures as well as specialized experiences such as private sunset charters and bareboat rentals for experienced sailors. The business highlights local knowledge of the Bay, tailored guest service, and vessel choice to match group size and trip goals. Bookings can be arranged for private groups and multiday voyages, and experiences are presented with clear duration options and vessel descriptions to help planners select the right charter. Chronic Sailing’s offerings are geared toward delivering professional, customizable sailing experiences that showcase Chesapeake Bay sunsets, cruising comfort, and safe, memorable time on the water.
Specialty itineraries include historical coastal routes, sunset photography opportunities, and family-friendly cruising plans designed to maximize sightseeing, relaxation, and on-deck comfort for every guest. on and off-board service excellence.