Italy Itinerary timing question

You qualify your questions well - that makes it a bit easier to respond. It looks like you have a diverse trip in mind. I can only assume that the trip matches your interests. 2 nights at Lago Maggiore might be enough for you depending on what you want to see/do. That really means 1 full day there, and of course 2 beautiful evenings. The trip to Varona will take a bit of time - expect a couple of train transfers. That limits your time there to 1 day and 2 evenings. When are you going? Is the opera at the Arena on your bucket list? (It's really wonderful!) I think you're going to be a little short on time in Verona what with transit, unpacking, packing for the next journey to Venice. Venice is really my favorite place to escape reality. It isn't art you look at, it's art and history you walk around inside. 3 nights is minimum! It's not a bad train ride from Verona to Venice so you don't lose too much time plus as soon as you walk out of the train station your experience of Venice begins. Somehow it's the only place I've ever been where the trip to the hotel is actually fun and intersting! Cinque Terre - hmm, not a big fan except for the seafood. I'll happily let someone else comment in my stead. Milan for 2 nights? I assume you are flying from Malpensa? Again you've given yourself a day and maybe a half in Milan. Enough for you?

Some are going to say, and it's true, that you will spend a lot of time packing, unpacking and dealing with trains. That's your choice and you need to take into consideration your 'wish list' if you begin to question your schedule because of the responses you get on this site. You ask if this sounds 'relatively doable'. It does. Does it fulfill your wishes in case you don't have a chance to return to Italy? That's your call. My suggestion would be to make a 'must see/do list' for each place and see if you are given them enough time . . . or maybe too much time. Whatever you decide I hope your trip gives you wonderful experiences and memories to fill your dreams!

So you are flying into Venice taking trains to all your destinations and then flying out of Milan.
You know what you want to see so I would say go for it.
Sounds like a good plan for a healthy young solo traveler that likes to be on the go.

First, thank you both for your encouragement. I do tend to try to get in a lot, but try to spend as much time “lingering”. A little bit of a juggling act. I am a huge art/history/architecture fan, but I never get to see the sea. As much as I want to see a bit of the Lakes, perhaps I need to cut that out. I reflected back to my trip to Nice and found that to be one of my highlights. That being said, if I had to make a cut somewhere, perhaps the Lake would be the cut.

I am flying in from Switzerland where I will have 3 days. Perhaps I can get my mountain fix there and rejig Italy. It seems a shame not to have a year to indulge in my travels.

Personally, I'd cut at least one destination. Just leave a bit more time for enjoying and taking in the experience, and less time spent traveling and transitioning place to place. If you are set up somewhere for 3 days and feel bored, you can always add a side day-trip. Whatever you decide, have a great trip!

I loved Verona, but I think either that or Maggiore is the place to cut. Cutting one night out of Milan would also be an option.

EDIT: I really like Como better than Maggiore, and I think many people on this blog feel the same way. So if you want to do one of the admittedly gorgeous lakes, maybe choose Como.

So this is the new and hopefully, improved itinerary:

Arrive mid-day Malpensa - stay overnight in Milan - prebook tours

Day 2 - head out first thing in the morning for Monterosso

Day 3- Monterosso

Day 4 - Verona - opera and tour

Day 5 - Verona

Day 6 - Day 9 - Venice

Day 9 and 10 - either Milan or ?

I think 2 full day in CT is good. I thought about going straight from Malpensa, but I arrive mid day and the thought iof a 4 hour train ride is not appealing.

As I have spent hours thinking about this, I would love some insight. As always, wish I had more time!

Thanks for all who contributed so far!
Has anyone done a good evening tour in Milan?

You mention that you are interested in Architecture. Does that mean architecture as in just looking at buildings, or architecture as in how it informs, influences and creates the built environment.
If it is the latter, then the Venice Architecture Biennale might be of interest. It is running now, ends mid-November. You would need two clear days to do it any sort of justice.

My Venice list keeps getting longer. I will check that put Peter. Thank you.