I'm in the preliminary planning stage for a trip to Tuscany, no dates set yet but it will be sometime in late Sept. or early Oct. 2025. It's a birthday surprise for my husband so I can't ask him for his input. We've been to Tuscany before and enjoyed it a lot but would like to spend more time there.
Day 1: Depart US for Florence
Day 2: Arrive Florence pick up car at airport: night in Volterra or someplace nearby (advantage staying in town can walk to dinner, don't have to worry about drinking and driving) disadvantage parking is an issue) or stay at Agriturismo near Volterra (4nights)
Day 3: Take it easy and explore Volterra (been here before)
Day 4: Day trip to Pisa and Lucca (skip Pisa and go tomorrow) entire day in Lucca?
Day 5: Day trip to San Gimignano (been here before) and Pisa
Day 6: Switch locations to other part of Tuscany: Maybe something outside of Siena or Pienza or in or near Montepulciano (Agriturismo or Country side B&B) (5 nights)
Day 7: Heart of Tuscany Drive
Day 8: Brunello Wine Country Drive
Day 9: Crete Senesi drive
Day 10: Siena
Day 11: Drop car Florence airport night in Florence stay B&B in Florence (been here before) (1 nights)
Day 12; Fly home
I can add a few more days if necessary
Thanks you in advance for your thoughts and input.