Greetings Dan,
Can I suggest you go to a local yacht club, find a regular sailor, most likely one who owns their own boat and buy him/her a few drinks to lubricate the conversation and then put the scenarios to them, because depending on what you want your character to achieve and the situations you wish to put them in, ie best hiding places, surviving storms, entry/exit processes out of foreign ports, it will determine their choice of boat eg if you wish to avoid radar, don't choose steel, if you wish to go fast or go in close to shore choose catamaran/trimaran. So many variables!!!!
Regards,
Rod
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