For your passport, please check to ensure it doesn't expire less than 6 months prior to your departure date. They won't let you leave the country and that would make us all very sad. The renewal process seems to be getting faster but give yourself ample time just in case.
We recommend Milan or Venice based on flight availability but Verona is another good choice if you don't mind connecting! You can easily get to our venue by train (approx 1-2 hours from any of the above) or rental car from Milan Malpensa (1.5 hours), Verona Villafranca Airport (30-45 minutes) or Venice Marco Polo Airport (2 hours).
This is totally up to you! While we'd recommend arriving in Italy at least 1-2 days before the wedding to help acclimate to the time change, we understand this isn't feasible for everyone. If you do arrive early, we'll have a quick Welcome Event to keep you occupied the night of Friday August 21st.