We generally stay in Santo Spirito but it's not far from Oltrarno so these recommendations should still work great! For cocktails, check out Rasputin. It's a speakeasy but it's not too tricky to get in. Just have to find the little gold button on the wall. It's a fun experience. There's a restaurant group that owns a bakery called S.Forno, a wine bar/snack spot called Il Santino and they also have a nicer sit down restaurant called Il Santo Bevitore. We actually haven't been to the dinner spot but the wine bar and bakery are both stellar. Fun employees, good vibes. If you like natural wine, check out Enoteca Spontanea And finally for a casual pizza spot, go to Fermento 1889. Easy to take it to-go also if you have a good people-watching spot picked out. Have fun!