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To qualify as a Shields skipper you should have significant experience as a sailing skipper, and preferably in large sailboats.  Contact the Marina Office or the Shields Fleet Captain by email (see link below) to indicate your interest.  

Plan on about a week lead time between your request and an on-the-water check out. A volunteer Shields qualifier will contact you. Qualifiers will provide familiarization and instruction with the rigging features particular to the Shields boat and will check to see that you are capable of sailing the boat. You must have already acquired the necessary sailing skills. Be prepared to provide one crewman. The qualifier will not act as your crew. If schedules can be arranged so that multiple individuals are being checked out, you will crew for each other. 

You must have your NAVSTA/MWR Qualification Card on file with the Marina or evidence of previous qualification at another duty station or equivalent sailing experience. You are encouraged to find an opportunity to sail with a Shields skipper for familiarization before your checkout. You are responsible for paying the normal boat rental fee to the marina during your checkout sail.

Contact the Shield's Fleet Captain for more information.