Second Wind

Yes — every boat on charter.boats is insured by its operator; we require it. The policy covers the vessel for fire, collision and third-party liability. You're only responsible for damage it doesn't cover, and that's capped at the security deposit.

Requirements vary by state and operator; no national sailing licence exists, so charter companies rely on a detailed sailing résumé (some states require a boater education card).

Chesapeake Harbour Marina sits right at the mouth of the Severn River where it opens into the Chesapeake Bay, giving you some of the most open water access in the Annapolis area. Read more →

Varies widely by region; the Florida Keys and Caribbean coast run year-round, while New England and the Pacific Northwest peak June–September.