Equipment
Unless he plans on crossing oceans in his C22 (& if that's the case, take it away from him NOW!), EPIRBs are WAY overkill.Get the USCG required equipment. Then make sure he has a USCG approved inflatable PFD (BTW, they're only counted as an approved PFD if he's actually wearing it). Buy him a handheld (at least) VHF for the holidays - DO NOT let him go out with only a cell phone. Cell phones aren't bad to have, mind you, but they're not considered safety equipment. The CG monitors Channel 16 on the radio so if he has any major problems he can contact them directly. If he's planning on singlehanding, a tether would be a wise choice. If he doesn't want to wear it, have him go out with someone else & tell him to jump overboard. He'll find out how difficult it is to get back aboard by himself, especially if the boat is under way, & will probably have no problems in wearing it.An engine spares kit might be a good idea, in addition to a good tool kit. Never know when you're going to have a fouled spark plug!Don't worry too much, Mom. He'll be great & you'll have the benefit of taking some nice summer sails!LaDonna