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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. For damage it doesn't cover, your liability is usually limited to the security deposit.

Not personally — this boat requires a skipper, who holds the licence. Generally, though: 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).

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