Is your Day 6 going to be a sort of organized daytrip? Like someone driving you to a couple of wineries? That could work.

I think your plan isn't bad at all. The very middle will be a little busy, but if you base yourself in Florence, you can easily do a bus to Siena one day, and your wine tastings another.

I like your plan. It is only 3 moves and 3 hotels.

I ignored your question about more time in Tuscany, because it just isn't that easy without a car. But someone like Luca from Hills and Roads can pick you up in Florence and take you wine tasting for a nice day out.

I don't much about wine in the Veneto, but there are many very good wines from the areas surrounding Rome. I've seen many mentions of Rome wine bars on this forum. People have some real favorites. I wish I could name them, but I can't

Thanks for your feedback! The wine tasting in Chianti will be an organized tour.

fivecents,

I much prefer Orvieto to Siena. You might look into training there and spending the night rather than taking day trip to Siena. Orvieto would be 1 hr train from Rome, but this would involve another hotel change, so that's up to you. You could see it enroute to Rome, but a large part of the magic is evening. Just a thought.

You can spend several more days touring tuscany - but woudl really need to rent a car - to do it efficiently.

I think for the time you've got, you've done a good job breaking up the trip in each place. One suggestion for optimizing your time in Florence since there really is a lot to do and see there: Consider doing a combined Chianti / Siena day trip. I did this on my last trip to Italy, when we based in Florence. I'm also a wine lover who wanted to tour Chianti but didn't want to have a car for that trip. We found a great guide recommendation on this board: Luca of http://www.hillsandroads.com/ - he was fabulous. I had particular wine producers and a restaurant that I wanted to visit and he let me customize the tour, but was helpful in making recommendations via email to streamline the day. He picked us up in Florence at our apartment and drove us around Chianti, stopping at a winery late morning, then lunch, and then the last winery in the afternoon which was near Siena. Instead of driving us back to Florence, I asked him to drop us in Siena where we spent a few hours and had dinner and then took the bus back to Florence. This also allowed us to maximize the 8 hours touring Chianti.

Siena doesn't take that long to see - admittedly I'm biased towards Florence, although I know some people adore Siena. This plan would allow you to see everything you want, but maximize your time in Florence with 2 full days there so that middle part of your trip is not so rushed: doing a Chianti day trip (gorgeous and worth it) that ends with a quick end-of-day visit to Siena.

btw… expand your Tuscan wine consumption in Florence with a trip to this fabulous and friendly wine bar: Le Volpi e l'Uva http://www.levolpieluva.com/Le_volpi/Prima_en.html On the other side of the Arno from the centro area, on a little side street, but worth the walk over.

Hope that's helpful - have a wonderful time!

Just to give you another perspective: I don't rank Orvieto that highly.

Siena is richer in art and history and has better shops, tons more churches, and the Duomo is to die for.

Orvieto is in Umbria and Umbria has towns that are more interesting IMO. Just MO, mind you, but still mine.

Are you interested in art? Architecture? Just curious.