valgalchi

I'm in the minority as someone who disliked Florence and loved Bologna. I also really liked Milan and felt it had a lot to offer (the Last Supper, the Duomo, the cemetery as well a flea market along the canal- great food too!). It's not the usual route but we did a day trip to Padua from Bologna to see the Scrovegni Chapel. You might consider squeezing that in if you can, it's incredible! I do second the suggestion of Siena as a daytrip form Florence.

KTtravel

As you can see, the "problem" with Italy is too many wonderful sites to squeeze it all in. I hope this will be the first of many trips for you. I would try to determine which places are your top "5 star" priorities and focus on those now.

If you do decide to keep Bologna, we also really enjoyed the Italian Days tour. It is run by Alessandro who is very engaging and enthusiastic.

kybourbon

*Total ~9 days in Italy across 5 close cities/towns.*
*We'll be there for roughly 11 full days.*

Have you added days? Are you flying from the US?

If you have 9 hotel nights, I would limit it to 3 locations. Did you just choose Milan because of flights? Do the two of you have any must sees that you feel your trip won't be complete without? I would start with a list of what museums/art you really want to see and then check days they are closed. You really don't want to end up in city on a day where the main thing you came to see is closed.

You can fly into Pisa, Florence, Bologna, etc. Or into Milan and back from Bologna or Florence. You do not have to fly in and out of the same airport. I prefer not to fly out of Milan because it's so far outside the city. For me, it depends on the time of departing flights and I usually don't want to backtrack to the arrival airport. YMMV. I've flown into Zurich for an Italy visit before and out of Rome before because my travel companion had never seen Amsterdam or the alps and likely wouldn't be returning to Europe. I arranged a very long layover in Amsterdam (most of the day - 7a-8p), spent the night in Zurich and then took the train to Milan the next day so he could see view the alps (not something I would normally do).

starrs

Great idea.
Now you've got me thinking....

SusanG

LOL! I love hearing from all the posters! chriswu0728, you gotta admit this is a knowledgable group. I might have missed it, but did you explain why you chose these places? For example, if you love art, or walking around a gorgeous town, seeing the historic buildings going back to the 1400s, Forence is indeed a must see. If you are interested in particular cuisines (I love all of it so am not familiar with the food of Parma for example) sounds like some of these towns are also a first choice.
But most of all, I do agree with everyone who says you should visit less places. We always want to see everything, but one of the greatest parts of visiting Italy is "la dolce via," and .. you miss out on that if you are rushing from one place to another. I would lose one of your day trips and instead use that day to stay in one of your spots a day longer

bilboburgler

It is vital to drink fizzy wine in a town square before the passeggiata starts, watch the movements around the square, the little flirtations the little glances.

richarde99

I recommend staying in the Oltrarno (across the Arno) preferably within a block or two from the Piazza Santo Spirito. From there it's an easy walk over to the main tourist sites, such as the Cathedral of Santa Maria del Fiore (15m) or the furthest we walked, to the Academia Gallery to see The David (20m). And when you return to your lodging, it's a different environment and feels less "touristy."

shelemm

Siena is one of my favorite places in Europe. It is divided into 17 neighborhoods (contrade), each with its own, flag, traditional clothing, museum (!), songs, animal totem, and dance. What a great place to explore. The renowned biannual bareback horse race around the campo pits the contrade against each other. So certainly spend some time there. (and I like it better than Florence).

If you are interested in regional food, you should look up what regional or even micro-regional specialties are there and find places that specialize in those. And eating is much more than going to restaurants; shops and bakeries will provide some of the most local experiences. If you stumble into a restaurant just because it looks good, you might eat well, but you might not expand your horizons.

Southam

It's always efficient to fly into one city and home from another, saving the cost of returning to the arrival city. Your tight schedule originally didn't allow for the travel between cities and needs all the time it can save. The itinerary must be arranged through a multi-destination search function, very common and easy.
I like Bologna a lot so I would start there, doing day trips as suggested. Plus its restaurant scene is mouth-watering.