Early planning stages - Italy - June 2027

How grand!
Look like it is shaping up well. I would make detailed lists for what you want to see in Florence, Rome, and Bologna so you can evaluate if you have sufficient time there. Those unplanned days could be applied to those cities if you want to do day trips especially, but otherwise I would suggest a smaller town or village in Tuscany. (Depends on if you want to drive or not.)

PS Count in nights—that better shows how much time you have (ie three nights gives you two full days and partial time on arrival/departure days).

For your coastal time, I’d check out the following places: Elba, Monte Argentario area, all of the Tuscan coast south of Cecina. If you want to head into Liguria, the Lerici-Portovenere area is gorgeous. You’ll want to book your coastal part early. Good luck!

Thanks for the suggestions!

We prefer to stay in locations at least 2 nights

This would be just 1 full day in a location. I would stretch to 3 nights minimum in most of your locations.

No interest in Venice? There is nowhere else like in the world. I would prioritize Venice over Bologna- unless you have specific reason you have chosen Bologna. You could actually get your "beach" time in Venice at Lido

I think you are shortchanging Rome in a big way- you will only have 1 full day there.

We would likely travel directly out from Rome on arrival day to our
first stop and then end our time in Rome before the flight back.

Good plan.
Where will you be flying from?
Have you looked at multi-city flights - in one city, out of another? (not 2 one way) it is usually under Advanced Search on airlines
sites. Obviously too early to book but you can use Google Flights to get an idea of what your flight options will be.

Have you visited Rome before? I understand your wanting to go directly to Bologna but I'd give some consideration to staying 2 nights in Rome (1 full day) at the beginning to get your feet on the ground and allow for any travel delays then doing 2 nights at the end in Rome. To me the 1 full day you have at the end is not enough.

I, personally, would not want another 2 hour journey + wait time for train + getting from the airport to the Roma Termini station on top of an international flight. However, that might not bother you. I fly from the Inland Northwest so usually have fairly long flights with layovers. Your profile doesn't reveal your location so if you are flying from the East Coast it might be easier/more doable.

Yes, we typically like to fly in and then head to a different destination and end our trip sightseeing where we will be flying out of. We love that flow better. We have just learned to not make big plans on that first travel day to allow for travel delays.

I was considering a multi-city journey and still may do it. Would love to see Venice, but would also love to see so many places it is hard. We had an amazing bucket list trip in Spain in 2019 and travelled all over in our 2 weeks and no regrets, but we also haven't really wanted to plan a trip like that again. Trying to narrow down the options so we can truly spend more time in each place. I'm not even really set on seeing Rome this time, the direct flight is nice though. We are still a bit scarred from the luggage that did not transfer from Munich to Paris with us a few years ago.

Three nights or longer is preferable; however 2 nights is the minimum we would do.

Bologna is on there because I have read that it is a good foodie spot, not too far from the other places we are eyeing, and my kid has been obsessed with Parmesan cheese her entire life and I thought a daytrip to Parma would be full circle. Haha.

Could be talked out of that though and plop Venice in that spot.

On our first trip to Italy, we chose to visit only two of the "big three," and it worked well for us (we visited the third on a later trip). It sounds like you're really considering what works for your family and your interests, and if Venice doesn't fit in, that's fine.

When we took our then 10-year-old daughter on her first trip to Italy, we included time in Bologna, and she said that she liked it because it was smaller and not so busy; your daughter may like that. You can go to a market in Parma, Bologna or probably elsewhere and do your own tasting of several ages of Parmesan, we did that.

Yes, it would be nice if you could spend a couple of nights in a smaller town in rural Tuscany, but time on vacation is always finite, and there's always more to see and do than time to do it! Perhaps your family could watch some videos, and decide whether you would want to trade off time elsewhere for time in a smaller town.

Enjoy your trip!

TBD ? What are you thinking?

To me, this looks like too much movement without enough “being there.”

What would it look like if you spread TBD around to some of your other stays? Perhaps TBD might simply be a day trip from Florence or Bologna. To Siena or Modena or Ravenna, for example. Orvieto? Endless possibilities.

What about starting in Rome (minimum of 3 nights, which is merely 2 full days, plus some orientation wandering - perhaps in the Forum - on arrival day. 4 nights is perhaps better.)? And booking your trip ‘open jaw,’ avoid backtracking to Rome and depart from ??? Florence? Pisa? Bologna? Milan? What would your trip then look like? How would you arrange your other 10 or 11 nights between Florence, a coast, and Bologna?

We once departed from Pisa. The airport was literally walking distance from our downtown hotel. Short flight to Milan then non-stop to Boston where we spent a few days to see our son.