Itinerary Feedback-first Italy Trip

It’s probably fine but I would never book an important thing on arrival day-flights are often delayed and climbing around on the Duomo terraces in a jet lagged state not a good idea!

Maybe drop the day trip to Lake Como?

I would drop the day trip to Bologna as well
Too much traveling around gets old on such a short trip (9 nights equals 8 full days)

Rome could use at least another night

I guess you like doing day trips. I would skip the Bologna day trip, I would do day trips to Siena, Pisa and Orvieto before day tripping to Bologna. Also Bologna is kind of a bigger city, not apt for a day trip. Siena and Orvieto have small, beautiful, historic centers with stunning duomos. You can visit Pisa in a late afternoon/ evening from Florence. In two or three hours you can visit the tower, baptistery and Duomo, or a little longer if you visit the cemetery (also worthwhile). The Orvieto day trip would be from Rome.

I see from your previous thread that you are not fans of museums so curious why so long in Florence?

https://community.ricksteves.com/travel-forum/italy/graduation-9-night-italy-itinerary-help

I suspect you are limited now by accommodation availability but consider staying in Siena, Lucca or Orvieto for a smaller town experience rather than 3 big very crowded cities.

Everyone has their own likes/dislikes, so this is just a suggestion:

Skip Milan. Land at Milan’s airport, Malpensa, and take the Alibus to nearby Stresa on Lake Maggoire or take the train to Lake Como. Yes, it’s a jet lag day, which is always beneficial to be outdoors. And we’ve taken multiple flights and multiple trains on an arrival day to begin at a good location. I’m assuming from your movement on other days that you could do this.

So, Monday/Tuesday is a lake set. If going to Stresa, explore the very close little islands with gorgeous gardens & villa.

The rest sounds fine, although there’s closer cities than Bologna for a day trip from Florence. But still not a bad choice, And food tours whether in Bologna or Parma are fun & a great way to try multiple local items.

I like the idea of skipping Milan. From the airport, go to Lake Como for two nights, then Florence, then Rome.

I would do something like this:
Bellagio or Varenna - 2 nights
Florence - 3/4 nights (Siena, Pisa day trips)
Rome - 3/4 nights (Orvieto day trip)

I think it’s a lot of moving around relative to r&r. On our first trip to Italy, we tried to see as much important stuff as we could. Rome, Florence, 5T, Milan, Venice, more Rome. By the time we got to Venice, we were burnt. We still enjoyed everything, because Italy is magical like that, and travel is too. But l would have done it differently on second go.

Your itinerary is better, but it involves a lot of time going from here to there and then back again. I dunno that I’d bother with a day in Bologna. Save it for next time. Do a food tour in Florence. If E-R is the home of the best food in Italy and Piemonte is 1A, Tuscany has a good claim to third. They have arguably the best wine (Piemonte is 1A again). They have the best gelato. Or get out into the countryside for a couple days and do the day trip INTO Florence from somewhere more to your liking.

I believe you’ve said museums aren’t your jam. But still, slow down and maybe see one. Or see some churches with art in situ.

One thing I’ve learned about trip planning is that you have to plan as though you will come back some day. You may never do so, but it gives you the freedom to leave something for next time.

How's your experience with jet lag?

I agree that this is a busy trip, with a number of day trips. What you do really depends on the interests of you and your travel companions. For example, I love art, especially painting, so my first trips to each of those locations focused on that, whether in museums or in situ, the original place that they were painted for. But that's not everyone's number 1 interest.

In terms of any day trips, calculate the travel time that you would spend doing each individual trip. Is that time from your eight full days in Italy worth it to you? Again, depends on your interests (as another example, I thought Lake Como was boring, but I' pretty sure I'm in the minority on that opinion).

I love Bologna, and it definitely has a different, less-touristy vibe than the other cities you're planning to visit.. As pointed out, Bologna is in a different region and has different regional specialties, so it's worth it for that, plus it's an interesting city (and has some good art too). But again, whether it's worth the travel time is up to you.

If you and/or your travel companions like Chianti wine, then a day trip to the Chianti area of Tuscany may be worth it to you. Difficult to get around without a car; you could take a day tour to the area. And, of course, it's beautiful. Or the wine towns of Montepulcino and/or Montalcino, but I don't know if they're accessible by train; I've only gone to those places by car. It would also be nice to see the Tuscan countryside.