Need some help with our Italian trip itinerary

I think the itinerary looks great. You will feel rushed in CT since you are not giving your self a full day there. CT is pretty awesome but it may not be worth the trip if you can only spend less than a full day there. You will also be going out of the way to your final destination in Venice.

As for your specific questions: (1) I think it is a good idea to stay in a hill town on Sunday and Monday so when you go to Florence on Tuesday and Wednesday you will be assured that everything is open. If you decide to stay in Siena the fastest way there from Rome is to take the bus instead of a train. You will not want to rent a car because driving one way with a rental car will cost you and arm and a leg.

(2) By "everything being closed" are you referring to museums and tourist attractions? If so I don't think we can answer that without knowing the specific museum or attraction you are looking at.

Hi Scott, thanks for your feedback. I am hesitating to go to CT because of shortage of time, but I've always always want to go there and thought inserting a trip to the coast would be a nice break from all those cities that we'll be visiting. I definitely will consider scraping CT altogether if I can't find a way to spend time there in a reasonable amount of time.
By "everything be closed" I meant restaurants, shops, and buses/trains. I'm a little concern with that since we'll be in small towns on Sunday and Monday.
Again thanks a lot. This forum has been so helpful for my trip planning.

I would scrap the CT especially considering the time of year.

I'd say leave CT for the next visit.

As long as you have the energy, looks like a fun trip!

1: For train prices, check www.trenitalia.it. Cars generally cost about 60 euros/day and up - more (say, 100 euros/day) if you want an automatic. Plus, an automatic will be harder to find. Remember, however, that depending on which "hilltown" you're talking about, the train station might/probably won't be right in the center -- so chalk in time for walking/busing your way to the center of the town.
2: Depends where you are. But yes, some stores/restaurants will likely be closed -- those that open on Sunday will also open later (say, noon).

Hope that helps!

Best,
Mandy

www.revealedrome.com

I agree with the advice to skip the CT this trip. I think it merits at least three nights and would be a great destination for your next trip to Italy. If you want a break from the cities, consider staying in a smaller town outside of Siena that you can daytrip to Siena from. I think the smaller towns are wonderful at night when the day trippers leave and the locals come out and walk around.

Thank you all for the advice. I think we'll scrap CT this trip and tag it with another trip in the future. :-)
If we are staying in Siena on Sunday and Monday, on top of the fact that we'll be there late Autumn, will we have trouble going to other towns like San Gimignano using public transportation?
I just read about the high tides in Venice. Has anyone encounter before? How bad could it affect our experience there?

Thanks again for all your great advice.

I have stayed in Siena on a Sunday and Monday in the fall and I had no problem with things being closed. Some things are closed or have limited hours but there will be plenty for you to see and do on a Sunday and Monday. You can spend a whole day just wondering around the town. You also shouldn't have a problem catching a bus to San Gimgnano, but again the hours of operation might be limited on Sunday.

I agree about dropping CT on a winter trip. If you want a charming town with a different feel, you could add Verona between Florence and Venice.

I think it is worth 2 days, but you could see a lot of it as a day trip - get an early train from Florence, leave your luggage at the station, then get an evening train to Venice.