First of all I would take some load out
. I don't like to sail boats near their maximum payload. No fun
and then I would sail to a place where I can stay out of marinas, can sail everyday to a different place, can go to a bar or taverna when I want, find easily food at cheap prices. Some more points, it had to have beautiful scenery, preferably clear and hot water.
I am missing something
, oh yes, nice chicks but I guess that I am englobing that on the nice scenery