If you're spending time in Florence, head to Trattoria 13 Gobbi. This was our favorite restaurant in Italy and where we happened to run into Conan O'Brien. Get the Florentine steak if you like your steak rare.
Also in Florence, stop by Gusta Pizza for the best 4€ margarita pizza you'll ever have. For another 2€ and the full experience, add a plastic cup of wine!
If you stop by the nearby town of Siena, you can't miss Osteria da Divo. The restaurant is built into a cave from 1000/1100 A.C. This is where Mike and Haley spent Valentine's day dinner 2018 (not getting engaged).
Apertivo is a tradition enjoyed by all Italians. It's a more fun version of happy hour, usually served with olives and other appetizers. We loved Signorvino, which has an incredible terrace over looking the Ponte Vecchio. This is where a bird pooped on Haley's head and everyone convinced her it was good luck.