Here is our proposed itinenary. We want a mix of touring and downtime and any suggestions regarding transfers. (Time estimates in parentheses)
Arrive Florence 5/16 - early afternoon.
Florence - 2 nights 5/16 & 5/17
5/18 - tour San G. and Siena (by bus or private car?)
5/18 - Rent Car in Siena. Drive to Montalcino. (1 hr.)
5/18 & 5/19 Stay Montalcino - 2 nights. Tour wine region.
5/20 - Drive to Chiusi or Orvieto to drop off car. Take train to Rome. (total 3 hrs.)
5/20, 5/21, 5/22 - Stay Rome 3 nights
5/23 - high speed train to Naples, then hydrofoil or get cab in Naples to transfer to Positano(total 2 1/2 hrs.)
5/23, 5/24, 5/25 - Stay Positano
5/26 - travel positano to capri - hydrofoil (45 mins.)
5/26 Stay Capri
5/27 - travel Capri to Venice - hydrofoil to Naples, cab from harbor to airport, and plane to Venice (total 3 1/2 - 4 hours)
5/27, 5/28, & 5/29 - Stay Venice 3 nights.
Depart Venice 5/30
Am I short changing something here and do you have any better transfer recommendations, particularly with respect to getting from Rome to Positano?
I am also thinking about maybe skipping Rome altogether.