Itinerary advice

I book airfare when I see a price I want to pay. I’ve done that nine months before trip; I’ve done that five months before trip.

You can set up an alert if you like. Just know there is no crystal ball with the exception that last minute fares probably will be the most expensive.

Bologna was underwhelming. LOVED Ravenna.
Also, Lucca, Sienna and San G were great.

Bologna is a fantastic city. Cinque Terre on a day trip one spe

I liked Bologna a lot as well. Huge historic district. Good walking tour offered by the tourist office.

Ferrera, Verona, Padua. Maybe an overnight there if you are a fan of Palladian architecture. So many interesting secondary and tertiary towns in region with Bologna as the central point.

Padua can be a rather inexpensive base, allowing you to see that city, Vicenza, Verona and Ferrara without traveling back and forth from Florence. For me Padua had more than one full day's worth of sights.

How long will it take you to get from where you're staying to the main train station in Florence (Firenze SMN) - 2 miles outside the city could be from the city limits or from the city center. Is there a regional train station nearby? That might save you going into the center, if you can use the regional trains - prices are much lower than the fast trains that only run from SMN, but the journeys are a lot longer. For instance, a regional train to Bologna from SMN takes from 1.50 to 2.15 hours, the fast train is just 35 minutes.

Getting to/from the CT takes a long time. If you have to commute in/out of Florence as well, it's definitely not a recommended day trip.

Also I did not quite understand these 2 kms. For instance Oltrarno is 1-2 miles from the Duomo (centre).
I think going to 5 Terre is time-costing. To take so much time, I would rather go to Elba Island or even nearer place duchesse as Uccellino/maremma/ Argentario district.
I do not like Bologna that much, maybe bécasse... I live in Florence part of the year. However I like Padova, Verona, Lucca, San Gimignano. I was also told Ferrara is fantastic but I have not yet been there.

Thank you so much for all of the advice. I did find great airfare and purchased it and I will gladly look into the other towns mentioned as well as alternatives for Cinque Terre.
My apartment is in the residential district of Campo di Marte and the host says the No 6 bus is very close and runs frequently.
Any advice on traveling to Pienza and maybe spending the night??

If I were staying a whole month in an apartment I would probably feel it was a decent enough value to afford to spend a night or two here or there so that I could more easily (and thoroughly) visit some places that were too far for a day trip. But at the same time, if you are settled in an apartment you can do some very long day trips. Get up really really early and be gone all day - since you can 'rest' the day before and after the day trips.

I think all the places you list are very 'worthwhile'. I love Bologna, Padua, Verona, Lucca, Pisa, and the Cinque Terre. I would probably do an overnight for that, and do it rather early in your time in Italy when it may be less crowded. Siena is an easy day trip and has so much I would probably do that more than once (by bus). And even though I hate tours, if you are really against renting a car you could consider some organized day trips to Tuscan vineyards and hill towns.

Check the bus routes - though I don't know where to do that. Google maps says buses #7 and #11 go from Campo di Marte to the train station (Firenze SMN) where you'd get trains and buses to other towns. Also note that on Sundays there is usually very limited bus service.