I remember your closing statement from the grad trip about " in the blink of any eye" still choke up from that!
I actually booked it around a star clipper cruise out of Venice through Croatia and around the tip of Italy ending in Rome.

So we are starting with a weekish in Corniglia ( Cinque Terra)
and then a weekish in Bellagio , leading up to 4 days in Venice prior to boarding the sailing vessel for an 11 day cruise.
In Rome for 4 days then off to Tuscany for 2 weeks, not too far from Lucca, ending with 4 days in Florence.

We are doing Air BNB all along the way and I did look at the Lake Como spot you stayed in, actually, before settling on Bellagio. I think it is so much more immersive to stay in a local home than a hotel.

I am planning on training everywhere with the exception of renting a car out of Rome so we can meander anywhere we want while in Tuscany! I am going to use your hiking app as well. MY big dilemna will be cellular I would like to find an option beside the $10 per day option I use currently. The time frame will put my bill pretty high at $10 per day . Also looking into surf shark which will allow us to use an IP as if we are in the USA and have better access to things my husband needs ( streaming TV, I know, dreadful)