Lake Como/Tuscany help!

Where are you coming from and going to?
Where will you pick up/drop car?

Lake Como really doesn’t need a car

The activities you mention would be found in Tuscany moreso than Como

Be sure you gave a designated driver if you will wine taste or have wine with dinner and all drivers have an IDP

You received some advice here
https://community.ricksteves.com/travel-forum/switzerland/switzerland-and-italy-trip

Coming from Boston to Switzerland to Italy. Renting a car in Como after our stay so we won't have it in Lake Como. Keeping it in Tuscany until Rome.

So you are going to both Lake Como and Tuscany?
To Rome at end of trip? Flying home from Rome?
You need to clarify what you are needing help with

You don’t need the car to get to Tuscany, take the train to Florence and pick up car there
Availability will be better there than in Como

Sorry for the confusion. I am asking for help for recommendations a home base in Tuscany with easy access to restaurants, activities and day trips. Also asking if people recommend to spend more time in Lake Como or Tuscany.

You really seem to be leaning more toward Tuscany over the lakes, but you have to realize it is a really large area packed with attractive destinations. I usually try to settle on a sub-region I am interested in first (for you, it sounds like Chianti/Val d'Orcia is probably what you are after), and then just start searching accommodations until I find what I want. There is a website devoted to agriturismi that you can check out: https://www.agriturismo.it/en

If you want to minimize driving on the boring 5 hour drive from Como to Florence you could take the train. I presume you will stay in the mid-lake area (the city of Como is not my favorite), so you would catch the train in Varenna and change trains at Milan Centrale to go to Florence).

You can rent a car in Florence, and there are several agencies near the station (Hertz, Sixt, Avis-Budget, Europcar).

If you plan to visit Florence, I'd recommend to stay in Florence 2 or 3 nights without a car, and rent it after you leave Florence to visit the more rural parts of Tuscany. There are many areas you can choose to see those villages of Tuscany, I recommend anywhere in the province of Siena.

for rental cars check www.autoeurope.com

Lake Como is a great place, but I wouldn't stay more than 3 nights (2.5 days). Unless you are interested in R&R, there isn't much to keep you busy for longer.
Florence needs at least 3 nights (2.5 days).
Tuscan countryside also a minimum of 3 nights.

Ok
Definitely more time in Tuscany

We love the area around Pienza, Val d’Orcia

Friends recently stayed at this place and loved it
https://www.a440intuscany.com/

They have a restaurant, onsite parking, beautiful views and great location
You can walk in to Pienza where there are a number of good restaurants

We loved this little hotel but they are likely booked up

https://piccolohotellavalle.com/it

Wherever you decide on you will need to book lodging ASAP in both Tuscany and Lake Como

Pick up car in Florence
You can drop it in Chiusi and take train to Rome