We are planning a trip to Italy in May with two other couples. We would like to rent a villa with 3 master suites if possible. Initially, my thought was to go to Tuscany as I love the area. I have been and would like to explore the smaller villages in the area of Tuscany/Umbria/Chianti area. We also plan to spend a few days in Rome at the end of the trip. One of the couples has been to Florence (we have too) and we don't want to do that again. Also, they have done some of the area as we have as well. I love the area and was hoping for a few weeks to just explore at a slow pace.
The other options are the Lake region or the Southern Italy (I have never been). I love the Lake region so that is a tough decision.
I have not been to Southern Italy, The Amalfi Coast, Positano but I have been to the Cinque Terre which I think is probably similar. Not sure I would have the same experience as the Lake region or Tuscan.
So, I am just struggling to decide. What would you recommend in Tuscany/Umbria area that would be different from what we have seen. We would love to go to a vineyard, have cooking classes at the villa and just visit some quaint small villages or walled cities.
thank you for your help I feel like I have been rambling so I am hopeful that I can get some god suggestions.