Sailing Charters in Annapolis with Chronic Sailing

Situated on the Chesapeake Bay, Annapolis, Maryland, is a gateway to some of the most rewarding sailing experiences on the East Coast. Chronic Sailing elevates this opportunity with an array of private charter options that cater to every pace—from laid-back sunset trips to energized multiday adventures aboard their impressive catamaran fleet. Whether you're looking to spend a tranquil half-day on the water or embark on an immersive three- to five-day voyage, Chronic Sailing tailors each outing to deliver both comfort and excitement.

The standout feature of Chronic Sailing’s offerings is their private, fully crewed charters, including signature trips like the Slowdown and Dos Milagros multiday journeys. These trips wind through the bay’s stunning landscapes, revealing shimmering water framed by quiet coves, classic marinas, and the occasional wild osprey or nibbling schools of fish beneath the surface. The Starz and Sweet & Salty multiday charters further extend the experience, inviting guests to unwind on spacious decks or swim in secluded spots where the water is cool and crystal clear.

Captain Shawn Owen and his crew bring deep local knowledge and a warm, professional touch that enhances the journey—witnessed by returning guests who praise the seamless communication, effortless navigation through Annapolis’s tight boating corridors, and the access to secret swimming holes. Bareboat charters offer an alternative for sailors who prefer navigating themselves with confidence.

Annapolis’s maritime heritage, combined with the modern luxury of Chronic Sailing’s vessels, creates a unique blend of tradition and adventure. This business stands out in a competitive market by focusing on personalized service, pristine vessels, and diverse charter options that suit families, groups, and seasoned sailors. From day sails timed for the golden glow of sunset to multiday expeditions designed for extensive bay exploration, Chronic Sailing is a top-tier choice for anyone eager to experience Annapolis from the water.

Whether you seek relaxation, skill-building, or celebration, Chronic Sailing’s offerings transform the Chesapeake’s waterways into a playground tailored just for you.