Lake Como to The Dolomites

For the Dolomites check out the regional website:
https://www.suedtirol.info/en/en/experiences-and-events

I'm a little confused.

Cooking class in Verena, do you mean Varenna? It's a ferry from Bellagio.

The Poschiavo part, not sure how this works. Are you driving from Riva and making a round trip on the Bernina Express to somewhere like St Mortiz on the middle day? Certainly possible but you could compare hotels in Poschiavo with those in Tirano at the Italian end of the line, they might be better value and taking the train from there would include the Brusio viaduct section.

For Ortisei, I very highly recommend the book Easy Walks in Val Gardena by Laurel and Richard Barton. As the title suggests,, it has easy walks/hikes with very clear instructions on how to access each one, whether hiking books and/or poles are needed, places to top for snacks or meals etc. Laurel is a contributor to this forum. In Ortisei town, there is a little museum I found interesting.

I took the Bernina rail (regular train) as far as Pontresina and back; it is the same route as the Express but cheaper and more chances to make stops. If I were to spend 2 nights in a Swiss town along the route, I would probably choose Pontresina over Poschiavo or Tirano.

In case you are not totally set on having a car the whole time, you don't really need one for Lake Como or Ortisei/Val Gardena.

The Poschiavo to Ortisei leg is between two places that look deceptively close on the map, but are very distant traveling on land. If you drive, there is the notoriously tiring Stelvio Pass; if you go by train you have to backtrack to Milano, or do Pontresina-Samedan-Zernez, then bus to Malles, again a couple of trains to Bolzano and bus to Ortisei; it is a sort of adventure on wheels.

the drive from Poschiavo to Ortisei doesn't have to go via the Stelvio Pass - I would (and the Umbrail) just for the fun of it, but I'd have a car with a manual gearbox and a suitable power/weight ratio. In an average hire car you'd go via Livigno and Müstair to get back into Italy. From Tirano you can go via Edalo and Caldero.

Pontresina is a nice place to stay but makes less sense in this plan. You would either leave the car in Tirano and take the train to Pontresina, stay the night and come back. Or drive to Pontresina, for two nights and take the train to Tirano and back - thus following the route three times.

Milan has three airports, if you are flying into Malpensa check if you can go to Como by train&ferry from the airport and rent the car in Como. You won't drive around the lakes, nobody does: Nobody likes tunnels.

There is a ZTL in any place you mentioned, Verona and Varenna included. Which one is Verena?

Thanks for all your thoughts. And yes I misspelled Varenna. Typing too fast.

We have been to Italy many times and love driving, at least I do. I always get a manual transmission. Part of the fun. We are not on any time crunch, although I will carefully look at our route from place to place. Stressful driving is not fun.

well in that case do consider the Stelvio Pass, check it out on Youtube. . But perhaps discuss it with nervous passengers before you go.......

From Tirano it's a simple route, just follow the SS38 north, it's the same road all the way from Tirano to Bolzano. This video covers the Bormio - Prata section

https://youtu.be/Vd64aAl072M

From Poschiavo head north to nearly Bernina summit then turn right into Italy and through Livigno to reenter Switzerland on the Ofen Pass, the head south to Santa Maria in Mustair, look for the Stelvio/Umrail sign and turn right. You enter Italy once again just before the Umbrailpass road ends at the junction with SS38.

https://www.youtube.com/watch?v=CcB8lAaGWFE this starts a little south of the Santa Maria turn at the 1:56 time, you would turn right where he turns left. The junction at 24:18 is where the SS38 is coming up and making a hairpin at 35:55 in the first video

It would be a fantastic drive - as long as it wasn't pouring with rain or low cloud.

I watched a bunch of videos of the Stelvio Pass. That is crazy!! I am going to show them to my wife before I even think about attempting it. I think she may faint just looking at them :). We shall see. If you had not mentioned it, I probably would have just taken it since it is a little faster than other routes. Thanks for the heads up.