We recommend flying into Pisa or Florence, which are both about an hour from San Gimignano. If you find cheaper flights into Rome, that is another good option if you are okay with a longer drive from the airport (about 3 hours). We recommend that you are in San Gimignano by the morning of June 23rd at the latest if you plan on attending the welcome dinner that evening. We are flying into Rome with an arrival of 9:15am on the 22nd and will drive to San Gimignano via rental car from there.
PS- Don't forget to check your passport expiration dates!!
To get from the airport to San Gimignano, we recommend renting a car for simplicity and accessibility. San Gimignano is a very small town with limited public transportation options. There are buses/trains that can transport guests from the airports to the town center, however public transportation options within the town will be limited. Pancolina (our venue) is about a 10-15 minute drive from town center. Even if you are staying at a villa that is walking distance from our venue, it might be wise (lol, get it?) to have a vehicle to make trips into town for food, exploring, etc during the 3 days of wedding festivities.
Below are a few available villas that are within 10-15 minutes walking distance from Pancolina (preferred so you don't have to drive after the wedding- no Ubers in this small town!):
https://www.agriturismocesani.it/ (10 min)
https://fattoriadipancole.it/en/about-fattoria-di-pancole/ (8 min)
https://ilcastagnolo.com/en/homepage/ (10 min)
https://www.hotellerenaie.com/ (15 min)
https://www.agriturismosansano.it/en/ (13 min)
https://www.casalari.it/ (15 min)
Below are a few hotels/villas near the town center (driving distance from Pancolina):
https://www.anticopozzo.com/en/
http://www.nomipesciolini.com/La-Torre-Nomipesciolini-eng-Description/
https://www.palazzobuonaccorsi.it/
https://www.palazzomari.it/en/
These are all suggestions, so feel free to stay anywhere you'd like! There are also a few options on Airbnb/Vrbo (search San Gimignano, Italy).