18 days in Italy. need help with planning.

We visited Rome and other parts farther south for the first time in December, back in 2012. I think we arrived sometime around December 10, and presepi, Christmas lights, and other decorations were already on display throughout Italy. It’s a magical time to be there.

We’ve stayed in Bologna more than once, but not yet in December. Italian Days does a full-day food tour, that I highly recommend while you’re there. Rather than using Bologna as a “base” for day trips, though, with 18 days I’d suggest staying in the other places you mentioned. Venice for at least 2 nights, and Florence for 4. Rome our first time was a full week. The train between Bologna and Rome passes through Florence, so you could stay in Florence (we always stay in the Oltrarno neighborhood, on the west side of the Arno River) either going towards Rome, or coming back towards Bologna near the end.

San Gimignano and even Siena could be daytrips from Florence, which could serve as a “middle base” of its own.

Hello chrislangq , and welcome to the forum,

Most people here advocate counting nights rather than days since this makes it easier to tell where you're going to be staying each night. This helps with reservations and keeping track of transit needs as well. Spending two nights somewhere gives you one full days and three nights, two days and so on.

If you are flying into and out of Bologna you should figure out whether you want to start or end your stay there and then determine the rest of your nights. Bologna airport is close to the city and has a tram to the central train station. If you want to stay in Bologna to start with I would probably take a cab from the airport into the city (~20e) and go from there.

The distribution of days is up to you but you list 4 big cities and one small town which is a lot for 18 days. The typical first trip to Italy is Venice, Florence, Rome so you're on the right track adding Bologna. Small Tuscan hilltowns are difficult to reach without a car or an organized tour. You have enough time to add some interesting side trips from some of these cities if that interests you.

Assuming 18 nights I would suggest something like this:
4 Bologna
4 Venice
5 Florence (side trips - Siena, San Gimignano)
4 Rome
1 Bologna (fly out the next day)

All of this - except SG - is doable by train with the fast train running between big cities. Keep in mind that many places - especially in Tuscany - will have Xmas fairs going on. Florence, Siena and Arezzo (near Florence) go all out and are worth considering.

Let us know what are your main interests, style of travel etc and I'm sure people will have further suggestions.

Have a great trip,
=Tod

How you checked airfare into Bologna? You can research on Google Flights. Often the smaller airports are more expensive and have less convenient connections. Just good to check before you develop your itinerary.
Wishing you a great trip!

Thank you all so much for the input! it is very helpful! as you probably guessed, my head is spinning trying to plan this!
Tod- I appreciate the suggestions and timing! I think we will plan around that type of itinerary. Much appreciation, and I look forward to hearing more suggestions of must sees. I would like to add in some memorable activities such as glass blowing or lamp working in Murano. When we went to Delft, we did a tile painting workshop and those are truly two of my favorite souvenirs, not just the tiles but the experience. I would like to incorporate an activity that "immerses" into the culture.
Kind regards,
Chris.

Honestly I would start with Rick's Italy book and some research watching some videos and other online content here. Rick's books do a good job of laying out the various attractions and his ranking of their importance or interest along with some indications of what might be of more interest to one group or another.

Check Rick's guide highlights here: https://www.ricksteves.com/europe/italy/rome

Honestly both Rome and Florence will eat up as many days as you can throw at them with attractions and many of those should be pre-booked so you need to decide on some "must sees" before you go. Bologna has a great city core and is mostly food-centric in its attractions. Venice has a few sites but is also much more about just going around and exploring the city itself.

In Bologna food and food making tours are very popular. In Venice you can row the canals with a school, tour an antique brocade museum or do other behind the scenes tours. Keep a special eye out for Xmas related activities and keep in mind the hours of daylight will be short - sunset around 4:30pm - and check the weather and temperature averages when planning and packing.

Have a great trip!
=Tod