12 Nights in Italy

I'm not a fan of day-trips to Venice, but if you must do that, the trip from Bologna will be faster than traveling from Florence. Still, it will be at least a 3-hour round-trip. I think it would be better to head there immediately on the day you fly in.

Sorry, can't help with the area south of Rome.

I was going to say the same re day trip to Venice. Not only a long trip, but a relatively expensive one and you pretty much need to use expensive Freccia trains. From Bologna, it is 2 hours on a Regionale Veloce for 12.60 EUR vs 1 1/2 hours on a Freccia for 34 EUR base fare each way. From Florence, it is 2 hours on a Freccia for 51 EUR.

We once made Venice as a day trip from Florence. It's a 150 mile trip by car, and quicker by train. It worked out fine as I'd been to Venice many times before. I wouldn't suggest it for a first time traveler, however.
Sorrento would be a preferable place to stay vs. Naples.

Sorrento is definitely a more serene base for three nights. Naples is very “active” if not chaotic, mich more than Roma. But on your last day, go early to Naples and enjoy the archeological museum as well as Rick Steves’ self guided walking tour. It will be a stimulating day.

You will enjoy Naples. Get there early in the day so you have time to explore this historic city.
I cannot imagine doing Venice as a day trip from Bologna. Either give it at leadt two nights or save it for your next trip to Italy. I would choose using my time in Venice over Sorrento.

Don't miss Pompeii Ruins. You can go there during the transfer to Naples or from Sorrento (half day.) By boat, from Sorrento, you can also visit the isle of Capri, Positano and Amalfi.

I thought Naples was great, but it’s definitely a more intense experience. I stayed in Sorrento, and regretted it slightly. Sorrento is a low-stress place, and it was a nice break after a long day of sightseeing. However, my taste of Naples made me wish I stayed there a couple nights. If you’re focus is Naples, Pompeii and Herculaneum then staying in Naples makes the most sense.

As far as sightseeing, the Capidomonte Museum doesn’t get much love here, but it’s got some superlative canvases by Parmigiano and Caravaggio. Pompeii and Herculaneum are very different sites and both worth visiting. Pastries in this part of Italy are incredible, get them whenever and wherever you can!

My guess is that you haven't been to Venice; if you had, you wouldn't want to day trip there. Why not start in Venice (2-3N)? It's low key - even in tourist season you can wander the back canals which are very charming and full of interesting things to see and do - and enjoy the most popular areas, the Rialto Bridge, Piazza San Marco, and the Grand Canal in the early mornings and evenings, when the day-trippers have gone. You can see the sights of Bologna in one day. You have options: leave Venice very early, check bags at the train station, spend the day in Bologna and continue to Florence; or day trip from Florence; or spend 1N in Bologna. 5N in Florence sounds like a lot. Siena is a good day trip by bus.

For the "south" where you stay depends mostly on what you want to see and do in the area. Sorrento is kind of a PITA to get to/from. It is a good base if you want to go to Pompeii, Herculaneum, Capri. It's not quite as good for the Amalfi Coast and there's not much to see and do in Sorrento itself. If you want to spend your time on the AC, Salerno may be a better choice, with good bus and ferry service to the AC towns and high-speed trains to Naples and Florence.

I spent 5 nights in Naples in February last year. As Harold has often said, the only sublte thing about Naples is its charm. I am a retired woman and traveled solo. I found Naples to be safe, though there were a couple places that I walked through feeling a little uneasy, but the only time I was in any real danger was crossing the street. Traffic is crazy and middle of the street is safer than corners (yes, even with traffic lights), because at least in the middle of the street, you can see everything that's coming. Naples is a little grittier, a little poorer, and a lot more in-your-face than other places, north or south. If you approach it with the right state of mind, it's a very good place to stay, unless you want to see the Amalfi Coast.

Thanks for the "shout out," Chani!

It was the Cadogan guide that I was using at the time (1994) that contained the line, "the only subtle thing about Naples is its charm." I found it to be totally true. It's a fascinating place, and perfect for those tired of the tourist hoards in some other places in Italy. But the "in your face" factor cannot be minimized (and remember I live in New York).

I agree with everyone else - either spend several nights in Venice, or skip it this time and see other places. In one of her other posts, Chani pointed out that she doesn't know anyone who, after their first trip to Italy, doesn't plan to return. She's right. So, assume you'll return again, and limit your targets on each trip (I only get 10 nights per trip, so that's what I do).

Most people like Bologna more than I did. But I took great day trips from there by train, to Ferrara, Ravenna, and Modena and Parma. Note that the timing of trains for day trips from Bologna can be a little tricky. The trains often left earlier than I would have liked; but, missing that early train meant a gap of several hours before the next one, which would have put my arrival near the midday closing at sights (meaning only a half day of sightseeing).