intheknoll

Hello! We're headed to Munich in May for our 25th anniversary, plan to get over our jetlag there and then travel to Northern Italy (we really wanted a little bit of Germany). We're not terribly interested in the big busy cities in Italy and want to make sure we get a bit of time in each area to stroll around without feeling too rushed. We're particularly interested in being near the coast. Any help and suggestions would be appreciated!

May 9: arrive in Munich
May 10-11: two days in Munich
May 12: train to Innsbruck in am, lunch, spend a few hours and take evening train to Verona.
May 13-14: two days in Verona (rent car here?).
May 15: drive to Como (stop along way at Garda - realistic?)
May 16-17: two days in Como
May 18: drive to Milan, stop for lunch and we are thinking about staying in Portofino or Monterosso Al Mare. Suggestions? We know we may have some trouble parking at either place. Wherever we stay we'll take the train to see the other.
May 19-22: three days either Portofino or Monterosso (little bit of R & R hopefully) Or is this too long here?
May 23: head to Florence? Or Bologna? Or any suggestions for Tuscany area? (We will only have 1 full day here, 2 nights unless we cut somewhere else)
May 25: Florence to Verona (drop off car) overnight here again
May 26: Train to Bolzano (stop for a break) and then back to Munich (realistic?)
May 27: return flight home

Jean

Could you fly open-jaw/multi-city into Munich and out of Milan? This would save you the time spent backtracking to Munich. Before you say the flights are cheaper, make sure you know the actual/overall cost of the backtrack and that you are searching multi-city flights and not two one-way flights.

I count 8 hotel stays and a string of several one-night stays in less than 3 weeks. This is your trip, but that wouldn't be enjoyable to me.

You don't mention anything you want to do/see that would necessitate a car. As your itinerary stands, having a car would be more of a negative than a positive. Most Italian cities of any size have a limited traffic zone (ZTL) into which you are not permitted to drive during certain (many) hours on certain (most) days... If you violate the zone, even unintentionally, you'll likely receive a traffic citation in the mail after you get home for each violation. The violation is usually captured by camera, and the rental company will give the authorities your contact information. Because of the ZTLs, driving into Milan for lunch isn't realistic and staying in either Florence or Bologna requires more thought on lodging location and then figuring out parking everywhere.

FWIW, traveling by train, esp. with an itinerary such as yours, can be freeing. The trains take you from city center to city center. No worries about ZTLs and no searching for parking. There isn't anything romantic about driving Italian highways/autostrade. If you're envisioning scenic, charming roads through vineyards and fields, you need to get off the autostrada and on to the secondary roads... and then double or triple the travel times between points.

If you're firm on the car rental and the flights can't be changed, I would pick up and return the car at Bolzano. Unless you have strong feelings about Verona, I'd skip it and add the days/nights to Florence/Tuscany/Bologna. Learn about ZTLs and how to recognize the signage.

https://mominitaly.com/ztl-in-italy/

Sassafrass

Jean’s point about backtracking is spot on, a waste of time and money. I do not think your trip is very well thought out. Either do multi-city, or if you are locked into RT Munich, on landing, go ahead and go straight on by air to the further city on your itinerary (Florence, Pisa, Bologna, wherever). You will be tired anyway, might as well press on. Re-plan the itinerary to be more linear, working your way back to Munich.
Then, put all time in Munich at the end if the trip, only one hotel stay there. Since you want a bit of Germany, putting all the Munich time at the end would allow you to rent a car there and do a bit of easy sightseeing and day trips.

Not that much time on the coast versus cities. You mention Verona, Milan, Florence and Bologna. If you don’t enjoy cities, why go? Just my opinion, but a day in Verona is plenty. If you are heading North, go to Garda for a couple of nights and just stop in Verona for a day.
Why even stop in Milan and deal with city traffic just for lunch? I sure wouldn’t. I would pick some pretty small town. Bergamo comes to mind, but others might have a better idea. Think seriously about where you will actually want a car.
This should come back to the top and hopefully, you will get a lot of good advice on re-vamping things.

Sassafrass

What do you want to see or do in Tuscany? Are you interested in the Art of Florence? Do you want to visit one of the lovely (but very busy during the day) walled cities like Siena or Luca? Is food the interest in Bologna? That is a good ways to travel for only one day and without some idea of your interests, no one can make good recommendations.
I note that you are stopping again in Verona for another night there. It is not a good plan to keep checking into hotels in the same places for overnights. It is more time and travel with no time in place to enjoy it.
You also stop for lunch during train trips. You have to stop when you are driving, but the advantage of the train is not having to stop. You would have to get your luggage off the train, check it in at the station, go get food, return and retrieve luggage, etc. a lot of hassle for what? Take food on the train with you and relax.

I question how much you will even want a car in most of Italy. Unless you will spend the day in Tuscany sightseeing in the countryside, you won’t need a car there and you don’t need to drive back to Verona to drop it off.

Getting real. Your plan shows 19 days including arrival and departure days, so you actually have only 17 days on the ground if that is correct. Your plan also uses a lot of time getting places.
Narrow down one base in Germany with a day trip or two and three in Italy. With travel between, that is what you have time for.

bilboburgler

if you are going city centre to city centre you really don't want a car

seat61.com useful to explain trains