I am planning to attend a wedding in Rome this September, which will be taking place on a Sunday. The group of friends I'm going with are planning to make a bit of a short holiday out of it, and one of us is from Verona so we'll most probably go and stay with her for a few days before heading down to stay in Rome for a few days more before the wedding. The current fixed plan is as follows:

Day 1: Verona - 3 days

Day 4: Rome - 3 days

Day 7: Wedding (Rome) - 1 day

Day 8: Depart

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However, I'm, thinking about extending my own stay in Italy by myself, either before or afterwards. I have a few more days holiday remaining this year use up, so was thinking either arrive in Italy a few days before getting to Verona, or stay on for a bit after the wedding (the others are most likely flying back the day after).

Looking at flight options, I have come up with the following options on which I'd really appreciate advice or recommendations (esp for the in-between parts when I don't know yet exactly what the hell I'm doing lol) and also what places you think I should skip (btw I enjoy food, landscapes, just strolling around a city and people watching, architecture, etc):

BEFORE

These aren't in any particular order, I've listed the cities that I would be flying to for each option even though most of them involve travelling and staying elsewhere before going to Verona.

1. Milan (6 days before Verona) - maybe 2-3 days, before taking the train to a town somewhere between Milan and Verona and spending the remaining days there, then another train to Verona
2. Turin (8 days before Verona) - 2-3 days, then train to either Genoa or Milan (assuming I can't do both due to time) for 3-4 days, then onwards to Verona
3. Turin (4 days before Verona) - 4 days here before train to Verona
4. Genoa (8 days before Verona) - 3-4 days, then train to either Milan, Bologna or Parma, spending a few days here, then train to Verona
5. Bologna (17 days before Verona) - yep this is a long one, only including it as flights are cheap on this date and I was basically looking at all flights to northern Italy. I was thinking perhaps to spend a good few days in Bologna, really getting to know the city and the food, then taking regional trains upwards to Verona over the course of a few days (I see towns like Modena, Carpi, Ferrara, Mantua, Ravenna on the map which might be worth visiting to get off the beaten track?) Also San Marino - worth squeezing in? Is it worth heading south a bit to Florence, Arezzo, Perugia, Ancona etc - bearing in mind cost of trains, ease of travel (I don't want to spend hundreds or make it a headache to get back up to Verona after this).
6. Trieste (8 days before Verona) - love the thought of seeing a different bit of Italy and Trieste seems very much like a "hidden gem" that people don't really talk about. My concern here is that it's a bit too far out and better to include in a Balkans trip. Potential schedule: Trieste for 3 days, train to either Venice, Padua, Bolzano or Trento (again, Alpine Italy would be cool to see), before another train down to Verona.

AFTER

My plans for after the wedding are a bit more flexible as I won't need to be in a specific place by a certain time. I have picked the following cities to base myself in:

1. Bari - spend either 4 days here, and fly home; OR; spend 3-4 days here, do some travelling around the local area (I also want to go to Lecce as I have a friend living there), then spend a few days in Naples or the tip of the boot, then flight home from Naples
2. Naples - again, spend about 4 days here then fly home; OR; essentially mirror the plan above but replace "Naples" with "Bari".
3. Milan > Trieste - train up to Milan for 3-4 days, then on to Trieste for another 3-4 days, then fly home
4. Florence/Genoa > Milan - few days in either of the two first cities, then few days in Milan before flying home. Is both Florence and Genoa feasible transport-wise if I want to go to Milan afterwards?

Aware this has turned into quite a long post, but thank you for reading and any tips or advice you can provide would be very helpful!