Where to start from Bologna?

Generally, the best use of your time (to save hotel/city changes) is to arrive, and then take the next train to your farthest destination, that way you can end in Bologna and only have 3 change days instead of 4. Since your departure city is in between your desired destinations, you're going to end up going one way and then the complete opposite direction to finish (maybe Venice->Rome->Florence->Bologna). I would probably say Venice first, as it's less hectic than Rome and good to get over jet lag in as you meander through the alleyways and between canals.

I am a big fan of starting a trip to Italy in Venice (getting over jetlag there and not having to deal with road traffic and being able to easily walk everywhere or take vaporetto rides). It's an hour and a half by train from Bologna, so a bit quicker than the 2.5 hours Bologna to Rome and immediately being plunged into one of the busiest cities in Italy.

The train travel times I'm giving here are the fastest, not what are the most convenient. Get the Trenitalia app and see what works for you. Sometimes I start looking on Google Maps for the trains, because it's easier, then switch to that app to make sure.

Going straight to Venice (or to anywhere except Bologna itself) does make for one long first travel day, but it's doable and we have done similar even longer first days and found it well worth it. I would be inclined to steal a night from your two final nights in Bologna and add it to Venice.

Then I'd take the 4-hour direct train from Venice to Rome, then the 1.5 hour train to Florence, then the half-hour train back to Bologna.

I don't know what time your flight to Italy is or when the kids' last day of school is, but see if you can get your family a couple hours onto Italy time before your leave home. The last time we took our son, daughter-in-law, and two grandchildren to Italy they did this and were glad they did. Remember to have meals at the right times, not just sleep.

Search the Italy forum for more details and post more questions as you have them!

@nancys8 makes a good case for Venice but I would also say that Florence is a good choice. It's the closest by train (30 minutes), the trains are constant and is essentially a small city in terms of walking and finding things. The downsides would be that it will be crowded and you will have to dive into must-see sights right away with you schedule being short. (Be sure to book must-see attractions ahead of time everywhere in summer but especially in Florence.)

I would argue for starting anywhere but Rome if you can avoid it. Rome is huge, chaotic, crazy and confusing and it's better to get smaller Florence under you and it will help prepare for Rome. The advantage of Florence over Venice first is that you have Venice to decompress after Rome and just before you fly home.

Bologna will feel tiny and quaint after Florence and Rome and is a nice, low pressure end to your trip after the "must see" onslaught of Florence and Rome.

My $.02, have a great trip,
=Tod

I would vote for Venice first. I have been to both Venice and Rome with jet lag and Venice is easier to manage. We flew into Venice this summer and my husband who always has had issues with jet lag had none. I would probably go to Rome next as you can take a fast train and buy your ticket ahead of time.

I haven’t been to Florence in years but it is a lot of museums and that is not the best with jet lag.

Oh Beth I didn't even think of that.....

I like museums, but museum days to me are a lot of standing and stopping, VERY slow movements as well as investing a lot of brain power to learn everything.....I would want to do Florence if I was more awake :)

A bit part of the attraction of Venice is just "being" there. There ARE museums, but many people spend a LOT of time just wandering about....meaning you won't be slow walking and standing and dealing with museum brain while adjusting from jet lag

I see you are 4 people, might 2 of them be younger humans? ;) I very much enjoyed my gondola lesson from Row Venice, that might be a fun activity during your stay :)

Two useful trip reports (one is mine) about Venice, etc. with kids:

https://community.ricksteves.com/travel-forum/italy/trip-report-venice-florence-rome-with-kids-11-9

https://community.ricksteves.com/travel-forum/trip-reports/bologna-ferrara-venice-rome-in-december-with-kids