Decided to start new post for next stage of help needed : ). Thanks to all that helped me from my first post to get to this point.
My 2 week trip ends up being 13 nights and 12 full days when I write it all out. I liked many suggestions of 3-4 nights in most places to meet our need for slow pace and relaxation. I would say we are looking for a mix of 70% scenery/wine experiences/Tuscan environment to 30% ruins/museums/history/big cities. We are an active, late 50's couple that enjoys wine/food/romance. Here's what I have come up with so far.....
Fly into Florence, hop train, to Vernazza CT - 3 nights
Train back to Florence, stopping at Lucca and Pisa on way? - 3 nights Florence
Train to Siena then car to Tuscany- Montalcino or Montepuciano - 4 nights at agriturismo
Train to Rome for final 3 nights
My thoughts are the chunks at CT and Tuscany can be relaxed and slower paced, the days in Florence and Rome to be more structured and with cities, crowds, and sightseeing. It feels like we are shortchanging a lot, but for our first trip we want to see the places we have dreamed about... I do see that we will simply have to plan more trips!
Am I correct that we can do trains all the way to Siena then rent a car there to drive out into Tuscany? And then where can we drop off the car before heading to Rome? Or do we drive it to Rome?
Thank you for any suggestions and opinions on this plan.