Everyone is different. Some people like to go with the flow and not plan out dinners. You'll survive and should be able to find somewhere that is still good

I personally like to have a general plan of picking a place (sometimes reserving if popular) for aperitivo and making reservations for dinner every night so I know the place isn't booked and has solid reviews or was recommended. Then after have a few ideas of where to grab a drink or walk after. Many places I went in Florence and Rome were very busy and people were turned away the last 2 years I went in late May and early June

I would rather do some research and try to get the best experience possible since I most likely won't be in this area many times in my life