You cannot get insurance for single handed cruising!!!! I tried and as soon as they heard single handed, the insurance guys instantly got real distant and unhelpful. Insurance for ocean passages is very expensive even with a crew. You can get insurance once you get somewhere but not easy or cheap for the intervening trip. If he was only going coastal cruising to Mexico, he might have been able to get a reasonable policy.

This is another example of a two way communications being a mistake. Best not to talk to anyone when your out at sea. while anchored in Typee Vai I missed an informal check in on a local net in FP because we were out hiking, etc. at the time of the net for two days. The moderator of the net was about ready to sic the gendarmes onto me because he got all worried that he hadn't heard from us. This was while we were in a protected anchorage where we'd been for a week already. Hate to see what would have happened if we'd been at sea.