Italy Itinerary-Need Advice!
 

My husband I will be going to Italy at the end of September for about two weeks. We have never been to Italy, so we are trying to make sure we are being realistic with our itinerary. It was cheaper to fly in/out of Rome, so we couldn't fly to Florence first. Here is what we have so far:

Day 1: Fly into Rome and take the train to Florence
Day 2: Florence
Day 3: Florence
Day 4: Leave Florence and go to Sienna or take wine tour day trip to Chianti
Day 5: Take train/bus to Montepulciano, sleep there
Day 6: Train to Rome
Day 7: Rome
Day 8: Rome
Day 9: Train to Napels/Pompeii/Train to Sorrento
Day 10: Sorrento/Capri
Day 11: Sorrento
Day 12: Train to Rome
Day 13: Rome
Day 14: Fly out of Rome
Any opinions/recommendations would be most helpful and welcome. We were also hoping to get to Venice, but I'm not sure what we should adjust in order to fit Venice into the schedule.

I think you have enough places for the time you have. I would move all the days in Rome to the end to save a change in hotels and splitting your time in Rome.

There is no train at Montepulciano. You could bus from Siena, and then bus to Chiusi to catch a train to Rome.
I would not change hotels---just stay in Siena and day trip to a Tuscan hill town or hire a driver for a day in Tuscany.

Ditto what Jami said. Definitely see Siena (its Duomo is better than Florence's; seriously) and do as a day trip, return to Florence that night (saves moving all your belongings about again and you don't need to use both bus from Siena to Florence and train to Montepulciano the next day) and then do the rest.

My revision would look like this:

Day 1 = arrive Rome, train to Firenze for 4 nights
Day 2-4 = Florence w/Siena day trip
Day 5 = train to Montepulciano, drink local grape juice in large quantities
Day 6 = early train to Roma/transfer to Napoli/Sorrento train for Sorrento.
Day 7-8 = Capri on one, Pompeii on the other
Day 9-14 = Rome

Hmm. Sounds good . . . you have extra space available?

Thank you for the great advice so far! We are thinking about switching Positano for Sorrento-any thoughts?

Thanks again!

So you're spending one night in Siena and one night in Montepulciano? Lot of travel there but maybe your goal is to see the Tuscan countryside using public transportation.

Take the bus from Florence to Siena; it drops you in the middle of the old city whereas the train station is outside the walls and you must bus or taxi in.

The Montepulciano train station is at some distance from the town. I assume there are buses and/or taxis to take you into town.

We took the train bus from Chiusi to Siena and, riding up hills and down past villages and farms and cypress trees, had a wonderful introduction to beautiful Tuscany.

Good advice from Jamikins. And I think you're going to have to skip Venice this trip.

I'm with bobthenavigator - I think you should spend the night in Siena on Day 4, take bus from there to see Montepulciano the next day, and return to Siena for the night. Next Day, train from there to Naples, where you can transfer to the Circumvesuviana train to Sorrento. I would stay in Sorrento - from there you can take the SITA bus or a ferry to visit Positano or other villages on the Amalfi Coast, ferry to Naples or Capri, and take the train to Pompeii, if that interests you. Travel around the Amalfi Coast is not as easy from Positano. After Sorrento, spend your remaining days in Rome

Depends why you want to go to Positano - it's nice. But Sorrento is the transport hub for Capri and Pompeii or Ercolano (Herculaneum) so it you're going to Sorrento area to explore Capri and the volcanic ruins, you're better off in Sorrento and you can take a day trip or short ride to Positano. If you're going for the beach (such as it is) then Positano is better. Plus, traveling from Positano to Sorrento for travel to Capri or the ruins means taking buses on the twisty mountain roads, which may not be fun.

Just so you know, the beaches on the Amalfi Coast are not sandy - they're gray and pebbly, and some are even just plain rocky.