Many different kinds of boats can be sailed. You do not need to own a boat to sail, nor do you need to charter (rent) one.
Outdoorsy camping wear can be used for most sailing. Going sailing would thus only mean procuring non-marking shoes and possibly a PFD. The PDF can be rented.
[Confessions of a Long-Distance Sailor http://www.arachnoid.com/sailbook/index.html] by P. Lutus