I am in the middle of details planning of 3 week Italy trip (21 nights) in June - family of 4 with two teenage boys (will be 19 and 16). All travels done by trains/public transport except for a small 5-night stretch of a heart of Tuscany tour. The entire Tuscany itinerary including Florence will be 8 nights - 5 nights heart of Tuscany car road trip and 3 nights in Florence (no car). Before the Tuscany stretch we will be in Rome - after that in Venice.
The car road trip section will most likely be Siena/Val D'Orcia area for 3 nights and 2 nights in Volterra (with a visit to San Gimignano). I know Rick advises pack very light and complete carry-on but we have tried that in the past but we have found that for a long itinerary with family, at least a couple of us needs to have 24 or 25 inch checked bags (even if the kids can go with carry-on bags only). So please use the assumption that extreme light packing (all of us with backpacks only) is out.
Logistically I am seeing 2 options:
Option 1: Round road trip from Florence
- Rome to Florence high speed train (1 hour 35 minutes as per Rome2rio).
- Either stay in Florence next 3 nights or proceed on the road trip directly.
- Either case keep the checked bags in Florence luggage storage and only take the carry-on backpack with just the clothes required for the 5 days. Pick up the luggage after the 5 night road trip is done while on the way to Venice.
- Advantage of this option will be to make the car road trip a lot simpler with respect to the luggage and we can do town hopping with one night stops.
- Disadvantage will be some backtracking.
Option 2: One way road trip from Rome to Florence
- Rome to Florence via rental car with all the luggage in the car including the checked bags.
- Advantage: no overall backtracking.
- Disadvantage: check-in/check-out will be hassles due to the bags and hence town hopping with one night stops will be out. We will have to have one or two bases from which to do day trips. Hence there is some inherent backtracking - as we have to return to the base after every day trip.
If you have tried either or both of these options, how was your experience? If you have tried both (not necessarily Tuscany but similar trips) what option have you found more convenient?