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Tuscany itinerary advice needed

So I'm still working on the details but here is the basic outline - all suggestions and comments appreciated. 28-30 April: Venice 1 May: rent car in Mestre early morning and head out. Stop at Lucca for lunch and a wander around. Leave for Siena. Spend the night in Siena. Wed 2 May: Head to San Gimagnano early morning for half day then back to Siena. Possibly market day in Siena... Wander Siena for remainder of day and evening. Overnight there. Thur 3 May: Montalcino and Montepulciano. Overnight in Montepulciano. Fri 4 May: Morning either market in Montalcino or go to Pienza. Leisurely drive back up toward Florence perhaps stopping someplace along the way (or we may spend more time just in the area and then leave, we'll see how we feel that day). Stop somewhere to drop off car, such as Siena, before going into Florence. Evening in Florence. Sat 5 May: spend day in Florence Sun 6 May: head home I'm starting to second guess myself and wonder if I should go to Montepulciano first and then onto Siena so its quicker to get to Florence, but then it makes the first day very long with a lot of driving to get to Montepulciano from Venice and it will make it difficult to see Lucca.... Any thoughts? Also, where is the best spot to drop off the car before heading to Florence?

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I dropped my rental off in Florence at the airport and took a taxi into town. You can also take a bus for less money. I did not want to deal with the dreaded ZTLs and even more importantly did not want to drive in Florence proper and am very glad I dropped off at the airport. Your itinerary seems well thought out to me but I am not an expert so I can only comment on what I know. Half-day is enough for San Gimignano more or less. you can always stop at Monteriggioni, which is convenient to both Siena and San Gim (in between them and basically on the way). Not much to do there but a nice wander and convenient/easy parking too. Very cute little medieval walled town I'd say it's worth a stop. I will say though that the markets in Tuscany are all pretty similar. I feel like if you see one in Siena you don't need to go out of your way to see another in Montalcino (I'd assume Siena's is bigger anyway but I haven't seen Montalcino's to compare). Also keep in mine that like most temporary markets, most of the markets close down by early afternoon. On your drive from Pienza (which is worth it for the cheese alone if you like that kind of thing) up to Florence, you have endless options to stop. How about Arezzo (basically on the way)? or you could always arrive earlier in Florence and spend more time there (IMO one can never have too much time in Florence:)). A better way to decide may be to think about your interests and what you'd most like to do for a while and pick a destination accordingly. Regardless, you will have a great time!