2025 Italy trip itinerary thoughts

There's definitely enough to see in Ravenna to justify spending a night there. (I had two full days/3 nights and had to push hard to get to all the mosaic-related sights.) In addition to the mosaics, Ravenna has a pretty historic center. There's a new historical museum out in Classe that I couldn't squeeze into my two days, since mosaics took priority.

Ravenna's definitely a much faster day trip from Bologna than from Venice, so I wouldn't under any circumstances consider a day trip from Venice to Ravenna.

I looked at trenitalia.com to see whether there was any advantage to traveling Venice-Ravenna-Bologna rather than Venice-Bologna-Ravenna-Bologna, but there isn't--unless you also want to see Ferrara.

I'm a big fan of Orvieto, but how practical it will be to take a train there from Tuscany depends on which town will be your last stop in Tuscany. Or perhaps (I hope) you mean you'll choose either rural Tuscany or Orvieto. The linkage of either of those with the Cinque Terre or even with Genoa might be more time-consuming than you're thinking.

Overall, this feels like an itinerary that's going to require a lot of time on trains or buses. That's pretty typical when you focus on small cities (which I often do myself). Just be sure you've done your research and allowed enough time to see your top-priority sights at each stop. In my view, there's nothing worse than spending a lot of time getting to a town and then having to rush away with goals not accomplished.

Thank you for your response. I would say we will need to reexamine our itinerary. Thankfully we are starting early to get things mapped out…..

We have been to Ravenna two times,once with an overnight (we were coming from Orvieto, and then continuing to Venice) and once as a daytrip from Bologna. Both visits were very enjoyable, and we saw all of the “in town” mosaic sites (the five listed here: https://www.ravennamosaici.it/en/

But we did not visit the sites that are out of town, as that would have required a bus or taxi ride. Either way is good, and you could choose depending on whether you want to make another hotel change, or not. It is an easy; daytrip from Bologna—-1 hour 17 minutes by regional train with no changes. If you do want to make it an overnight, look at Palazzo Bezzi, a nice 4* hotel within easy walking distance of the train station.

And if you wish to include Rome, that is a short journey from Orvieto, and could fit before heading to Cinque Terre. But if you are spending 3 nights each in Venice, Bologna, Tuscany/Orvieto, and Cinque Terre before returning to Milan for you flight hom, I don’t think you have time unless you made the trip the full 17 days.

Looks like a lovely itinerary.
We usually use Bologna as a base. We took a lovely day trip by train to Ravenna, joined a tour we found on Get your Guide to see the amazing sites.
We had a wonderful lunch and then spent more time walking around.
In my opinion, a day trip to Ravenna from Bologna would be perfect.