Please help me pick 2 new cities

I am not a fan of Verona, but many on this board are.... I'll let them speak. I love Bolzano and the Val Gardena, and Bolzano alone might make a good northern Italy stay for 4 days. You can take a bus into the Val Gardena and a lift up to the Alpe di Siusi. Just a thought. It is magnificently beautiful. As to the south, I think Sorrento would make a nice base. It's small, but worth a day in itself, great dining, views. Access to Pompeii, Ercolano, Amalfi Coast, even a day in Naples. Rick Steves' guide lays out a great set of options for a Sorrento case. Sicily is an outlier on your itineary. There is too much to Sicily to "see" much of anything in 5 nights, and it requires a car.

Thanks Laurel! The more I read about Torino I'm really liking the sounds more than Verona, but I'm going to read more about Bolzano too. Appreciate the insight on Sicily especially!

North Padua or Bologna South Sorrento or Positano - along the Amalfi Coast. Sicily is very large and public transportation is possible, but not the best. Most rent cars. You could spend 2 weeks in Sicily and still not see it all. You could pick maybe on area.
I would suggest flying to Sicily, if you go.

Laurel can you also share why you aren't a verona fan? I'm well aware I'm overthinking this, I just really love Italy so much that it's always hard to decide where to go when I start. It seems like every town I read about or see photos of appeals to me. Go figure! I just read about Trivoli (obviously not North) and it sounded amazing too. I think Sorrento sounds perfect for the southern spot. I'm going to focus there.

I enjoyed Verona very much. I found a lot to do there and I think it would be a good base to make trips from.

I find Verona to be one of the prettiest towns in Italy, but different people like different things. I suggest you do some research on line, then use Google images to take a look at pictures of the places that spark your curiosity.

I have been to Sicily many times using public transportation, but Sicily is a trip in itself. You might enjoy Ravenna, Ferrara and Mantova - all are near Venice. Padova is also a great choice, either as a daytrip or an alternative base to Venice (although I love waking up in Venice). Pistoia also has lots to see and is a little off the main tourist track. In the south I love Paestum and Ravello. Post again or PM me for specifics.

I love, love Verona. Lots to see. Great walking city. Roman ruins, great churches. The Adige river runs through Verona. Its a lovely city...make sure you look down....many Roman ruins, some covered by glass, some just exposed with railing around them are to be seen below street level. Stay on the Piazza Erbe is you can...the market sets up there each day and the main shopping street that runs to the Piazza Bra is close by (I forget the name of it....seems like it is via Mazzini).If you haven't been in the lakes area, I would recommend Stresa on Maggiore. Great walk along the promenade by the lake, boat rides to islands in the lake, can take day train trip around the area. Cannobio on the far end of the lake close to Switzerland is another favorite town of mine. You can't go wrong with Turin either. A great city. Have fun!

Bologna and Assisi. You didn't list Orvieto, so that might be another good alternative.

For the North as an alternative to Verona could be Lake Garda. Easy day trips to both Verona and Padua. Or head up to Lake Como. High Speed train from Venice to Milan. If you are there for a couple of days you can even venture across to switzerland and visit lake lugano and the town of lugano for a day trip.

I'll admit to being a HUGE fan of Verona. We loved it so much in May of 2011 that we went back this past May. Here are some of the highlight photos from both of those trips: Verona Highlights 2011 and 2013. Verona has quite a few easy daytrips from it by public transportation, including Vicenza, Padova, Lake Garda, and Venice, of course. We also loved loved Orvieto, another option mentioned above. It's down closer to Rome, just beyong the Tuscan border, in Umbria. Here are some of the highlight photos and video clips from Orvieto in May 2011

if you like lucca, volterra is a good choice.

I second Ravenna. If you're interested in Byzantine mosaics, this city is for you! I went for a day trip but wished I had stayed overnight.

Assisi. We were just there last month for five days and would go back tomorrow if we could. - Train accessible: check. - somewhere quaint, but with sights of its own: check. - easily accessible to some other towns to day trip to: check. - good wine and food: check. - historic(ancient, archeological, churches, anything!): check. - not a hustle and bustle modern city, think serene with character: double check.
- breathtaking views: check. All that and more.

You guys are awesome! Thank you!

Another vote here for Verona. We go for 3 weeks every summer. Love, love, love it. The main rail line from Venice to Milan goes through it (but make sure you get off at the right station, there are 2). It's easy to get to Matova, Padua, Vicenza or Milan.
Last time we stayed in a lovely apartment in an old Palace, right in the heart of the old city. The owner, Carlo, lives there and speaks good English. If you're interested, I will send you his email address, or you can look him up on Tripadvisor, it's Antica Verona.

Here's one outside your specs. San Gemini, Umbria. Rent a villa for a week and enjoy Italian village life.

@Gordon - wouldn't that require renting a car to go see a lot of the sights?

If you go to Bolanzo definately check out the South Tyrol Museum and see the Otzi the Iceman exhibit.. so very interesting.