Sorrento or Siena?

I vote for Sorrento. It's my 2nd favorite place in all of Europe - Paris being my 1st.

We've been there 3 times for 5-6 days each time and love it. It's relaxing, fun, beautiful, good mix of old and new, it's a "real" town filled with warm and friendly people.

Can't really answer the question you asked...but.... try to make it to Palermo while you're in Sicily. Wonderful place to experience some of Italy.

Since you will be in the "vicinity" I would check out Sorrento and the Amalfi Coast. Tuscany is a little out of the way.

Do I understand your itinerary correctly that you'll 'cover' Sicilia to Venice, and places in between, in just about 12 days? If I've got that right, I think narrowing your scope a bit makes some sense, or you'll spend more time on trains or in a car than experiencing Italy. If you're flying into Rome, maybe stay three nights there (lots to see and do), then head down south for the wedding. After the wedding, I think I'd stick with Paestum, Sorrento, Capri, the Amalfi Coast and Pompeii (same general vicinity) before flying back. I love Florence, and prefer it to Rome, but maybe you could take a day in Rome and day trip to Florence via high-speed train (about 90 min, I think). Are you also flying out of Rome? That could change things, too, perhaps putting Orvieto in play for a night or two?

Given the time limitations, I'd go to Siena. You can stay in Siena and take the bus into Florence. It's not a long ride. We found Siena to be a nice complement to Florence. Sorrento is wonderful as well. You've got a tough choice and you won't go wrong whichever one you choose. Besides, you'll have an incentive to return. Ciao.

A very full schedule for a twelve day trip would be Rome, the wedding in Taormina and days in Sorrento to see the Amalfi Coast/Capri. I would leave the destinations to the north of Rome for a future trip. There are different opinions of what it means to 'make sure I get the most out of my trip." Hurrying through is like gulping down a gourmet meal. You finish eating it and you don't really remember the way it looked and tasted. Take Italy one bite at a time and enjoy it. You'll be able to taste the rest of it on a later trip.

It all depends on how you are travelling to Taormina. I spent 5 days there and part of my travel group took the train from Rome while I flew down. They essentially lost a day on the train.Since you are going to have 2 days in Tuscany, I think you should blast down to Sorrento and see if you can fit Herculeum in on the way down or the way back.You'll need a car to do this well. My experience has been very favorable driving in Italy, but it does take some getting used to.Flying down on Thursday afternoon could get you Wed. night in Sorrento which is well worth your effort.You also want to have a full night in Venice to experience it after the tourist hordes leave.

If you love history, you could take the train from Rome to Ostia for a 3/4 day trip. We loved it and there is a Rick audio tour to accompany that.

Another idea- from Florence, there are day trips via bus- tour type things.