Charleston Harbor Sailing

Charleston Harbor Sailing is a small, relatively new (est. 2023) private charter operation run by a mother-daughter team out of The Harborage at Ashley Marina on Lockwood Dr, offering intimate sails for up to six guests aboard a 35-foot sailboat called 'Esprit de Joy.' Reviewers consistently praise the knowledgeable, personable captains — including Captain Will, an active competitive racer who placed first at Charleston Race Week — and the clean, well-maintained boat. The main friction point flagged across multiple platforms is the parking situation: there is no on-site parking, and guests must pay for a spot at the adjacent Courtyard Marriott and walk over, which can catch first-timers off guard.