New Italy bound

Doesn’t look too exhausting to me. Why Milan for 2 nights? I would personally land in Milan and hop on the train to my first destination..

Lots of people here don't like Milan. I definitely think it is worth a night or two. Schedule ahead of time to see The Last Supper. See Michelangelo's last Pieta at Sforza Castle.

Welcome to the forum, Antonia!

I'm sure you're very excited; Italy is a very exciting place to go! Some more information might help the gang here to better help you? It would be interesting to know why you chose the locations you have for this first trip? What sorts of activities do you think you'll want to fill your days with in Varenna, the CT and the A.C.? That may determine where you'll want to concentrate your time. What can you tell us about yourselves? Any specifics, such as mobility challenges, we should be aware of?

I notice that, aside from Milan (why 2 nights Milan?) all of them are "water" locations and there's a curious absence of any of the The Boot's "Holy Trinity": Rome, Florence, Venice. That's just fine if you don't think they will trip your trigger but you may want end your trip with 3-4 nights in Rome to be close to a large departure airport + get a good look at the Italy's old and interesting capital city. The A.C. is just remote enough that getting out of there to catch same-day planes home can be risky, and Fiumicino (Rome) tends to be the closest choice for international flights. I am, of course, making an assumption here on how you envision leaving the country so if you have other plans....?

Otherwise I don't think your plan will be exhausting as you thankfully only have a couple of 2-night stays. The clock is ticking here however as the popular water spots started booking up many months ago. You'll want to put the giddyup on nailing down your accommodations if your trip is just a couple of months away. :O)

Travelling to & from Cinque Terre for only 2 nights would be exhausting for me. Then day 8 would be totally lost in transit to Amalfi area with several train changes. If your trip is for this Sept, accommodations may be slim picking by now as all areas you’ve chosen are in very high demand. We spent 6 nights in Positano to enjoy the area but even booking 9 months in advance, many places were sold out or well over €300.

Where are you flying back from? I would stay at least one night close to the airport to avoid travel mishap anxiety.

Not necessarily IN the airport but close enough that a taxi can take you there even if one road is blocked.

I don't think your pace would be exhausting for a 2 week trip. Many people enjoy staying along the Amalfi Coast rather than in Sorrento, so don't be dissuaded. I've only stayed in Positano, but other posters have mentioned enjoyable stays in Amalfi, Ravello, Praiano and other smaller towns. No matter where you're traveling from it will likely be a long train ride just to Naples, so consider a private transfer to your Amalfi Coast destination. The extra expense might be worth it. Or if staying in Amalfi or Ravello, you could take the train to Salerno and then a ferry to Amalfi. The other thought I'll add is that Cinque Terre is a bit of a detour and another water location. You might consider replacing Cinque Terre with an end-of-trip stay near your departure airport. If you're departing from Milan, then you might also consider going straight to Lake Como upon landing (only an extra hour by train) and saving your Milan days for the end of your trip. If that creates extra days and you don't wish to stop in a larger city like Rome, Florence or Bologna, then Orvieto, Modena, Parma or even Verona would be good options along the way back to Milan.

I haven't been to CT.
My wife and I were just at Positano and thought "we don't need to go to CT any time soon"

The point being that both coasts have steep cliffs, beautiful vistas, ....
CT seems less posh and also better for long hikes
If you're pressed for time, skip one of them and see it another time.

I've been to Cinque Terre and the Amalfi Coast and I agree with Evan--I would not feel the need to visit both on this trip. I would rather have more time in one place.
Where do you fly home from?

We stayed two nights in Milan, but one of those days we did a day trip to Lake Como and on our other day visited the Duomo and Sforza Castle. Otherwise, we weren't overwhelmed by Milan.

If you have an extra night to add, I'd give it to Cinque Terre if you do decide to go there - you have a long train day to get there - using rome2rio - going fr Bellagio to (I picked) Vernazza is a good 7.5 hrs, also taking into account getting to and from your accoms to the train station and whatnot - that's pretty much a whole day lost to transit, giving you only one full day in CT. If you have two nights to add - one to CT and one to AC. (As others have mentioned, you don't say where you're flying home from...?).

Then from CT to Amalfi (using Vernazza to Sorrento) is another exhausting 7 hr train/subway ride, and if you are staying somewhere further along the coast, toss in a bus ride (unless you hire a private driver say in Naples). We stayed in Atrani ('around the corner' from Amalfi) and that was another 90 min on the bus, after JUST missing the bus in Sorrento and having to cool our jets for another 30 min...not to mention the traffic the bus may encounter which slows you down even more.

Now - having done CT twice (2008/12) and AC once (2014) - the great thing about CT is it is much more compact (and sadly now prone to overcrowding - I'd hesitate to recommend anyone go now) and you have the trains to get your around easily. There really isn't much to do other than poke around the towns and the hiking trails (if they are even open). AC is much more spread out, and you are either using buses or the ferry of it's running. We only had 3 nights and I think 5 would have been perfect. One of our days we had a private driver and the other day we bused to Ravello and hiked back down to Atrani, but there are so many other towns I'd love to have seen.

Personally - as someone else mentioned - you have a lot of 'water' spots on your visit. If it were me, I'd prob skip CT and toss some nights into Rome or Florence, or even somewhere like Orvieto or Naples. If you wanted to head right for AC, you could even fly Milan to Naples pretty cheaply and much quicker.

Where is return flight leaving from? No Rome on this trip?

Thank you All for your very helpful & insightful advice!
We now have a grip on our plans as follows: start 2 nights in Milan , train to Bellagio ( no rooms available in Varenna) 2 nights there, then train to Florence ( haven’t done train routes yet!) for 3 nights. See as much as we can w tour to Siena, San Gimignano, & one other town... getting weary of planning.... THEN train to Sorrento for 3 nights, train back to Tome 2 nights & fly home to Boston!
Any advice on the train travel will be appreciated ☺️ Thank you
Anne