hey hey aniello.autumn
where exactly are you staying for the wedding? what city (airport) are you flying into and what city (airport) are you flying home from?
like many other travelers want to see more than you really have time, staying a day or 2 in places is just not enough. check-in times 3-4pm and check-out times 10-11am. gives you half evening then check out next day. you want to be in the city of departure night before, make sure the airline departure times (some may be early early mornings)
if you are renting a car, all drivers will need an IDP (aaa.com/IDP), read up about laws, rules, signage, ZTL zones, parking, speeds to not get a $$$ ticket, cost of fuel and if cash or card payment driving times will take longer than you think what he says on driving maps. when do you plan to pick up car? i recommend not driving far after a long flight, not knowing where you going to the new area, check picking up car in one place and returning to another place. you don't want to be back tracking which adds time and costs.
where ever you stay, make sure you have a parking spot, an issue in many cities with a parking garage in a different area that you walk with luggage on cobblestones/uneven pavement, two lanes winding roads at times, could be slow with traffic, if stopping where do you put your luggage for safety reasons. when and where to return car, hopefully night before flight home
make a map of your plans/route of what is really advisable with travel times. october is a busy month with harvesting of wine & olive oil, festivals/fairs happening. lots of things to think about before arriving but if you are all prepared with your notes you'll have a great time. keep asking questions, the volunteers on this forum are here to give you advice, best way for this and that, good bad and ugly. your decision what floats your boat. good luck
aloha