First time in Italy, need help!

Hello,

A friend and I are celebrating our 40th birthday(s) in Italy this September and we would love some help/suggestions to help planning.

We are two single gals that are traveling as budget friendly as possible but still want to stay in accommodations that feel safe, friendly and offer private bathrooms. We love meeting other travelers and are open to homestays or local b&b's when possible. My dream day in italy would include seeing art, exploring the history, eating homecooked food with locals and dancing with cute boys haha. I am vegetarian but no other crazy restrictions. We both love wine, and we would love to meet folks our age and be away from touristy crowds. We have a general itinerary planned but need some support:

1. any cities we should edit/add/remove
2. where to book trains vs renting a car
3. any recommended places to stay. people to meet, places to make reservations for now, etc would be very helpful
4. help around planning our time in Tuscany & Sicily, we want to see a lot but also prefer slow/easeful travel vs maximizing output.
5. any tours or excursions you recommend
6. things we MUST see/do in certain places

We basically are feeling a little stuck on how much we need to book now and how much we can "wing it" when there. We are currently trying to figure out housing that is flexible with our time.

Our itinerary:

August 23-28: Geneva

August 28-1: Venice

September 1-8: Dolomites (mostly booked but open)

September 9-11: Florence

September 11-16: Tuscany (we booked a farm stay in Volterra but dont know if we should book multiple stays across different regions or stay in one place and do day trips)

September 16-20: Ischia/Naples (other day trips)

September 21-24 Ravello/Amalfi (but we are thinking about skipping this bc we heard its very touristy and expensive)

September 24-30ish: Sicily (should we stay in one place, move around?)

I'm new to reddit and new to Europe so appreciate kindness and curiosity!