Re: Hopefully Getting this Done -Most of our Time

1. Tuscany Hilltowns are one of the few places in Italy where renting a car probably makes sense for most travelers. Train to Orvieto, pick up rental car there, and drop it off before getting to Florence and strenuously avoid driving the car into the Florence city center.

2. Home base in Orvieto, Siena, or one of the Tuscany Hilltowns in between those two--but only for the Tuscany Hilltowns part of your trip, not for the Florence part. To see Florence, stay in Florence, give it at least two full days, and get rid of the car before your first overnight in Florence.

3. This is too big a question to answer here: you will just need to do your own research, you don't want to be limited to the few hotels or restaurants that will be mentioned here by other posters, it's too small a sample of the total choices available to you. For restaurants in Florence and Siena, use the restaurants section of the viamichelin.com website and look for Michelin recommended restaurants.

4. Your weather data is not too far off but a little off re 80s: average temps are not in the 80s that time of year, even in Rome--80s are possible but only if you hit an unusual bit of weather and you can always take off layers to cool off but plan for evening/night temps that could easily dip into the 50's at night.

Cindy - if you are considering renting a car then look at viamichelin.com. It will help you with planning your itinerary. Tuscany is a pretty large area. I'm not even sure that two of the places you mention - Orvieto & Chianti are actually considered part of Tuscany or part of other regions. Anyway, using viamichelin you can get an idea of how far away the different towns would be and this can help you to plan whether to base in two different spots or not.

Our first trip to Tuscany we stayed near Arezzo, about 30 minutes south of Florence. We were there for a week so didn't mind taking some long day trips - the longest was to Assisi (again, maybe not technically in Tuscany). We also drove parts of the Chianti region and visited Siena. On our 2nd trip we stayed near Pienza and visited Montepulciano & San Giminiano on our way to Lucca. I can't imagine having done all those places from just one spot.

The great thing about Tuscany is that you really can't go wrong. It is so beautiful and there is SO much to see that you can't possibly see it all in one trip so don't even try. I would base myself out of one area (and personally I would not make it Orvieto) and see the towns immediately in that area and save the rest for another trip. Once you get a better feel for which smaller section of Tuscany you would like to visit, then I'm sure you will get better responses to the hotel question.

As for dress - I'd wait a while to see how the weather is trending. We were in Rome our first time in mid-late September and it was HOT. But our first time to Venice was in the summer and it rained and was much cooler. And in Tuscany it was very hot during the day (summer both times) but cooled off nicely in the evening. I would imagine that the weather would be nice enough for you to be able to still pack some lightweight summery things for Rome and add a sweater, light long pants for the latter part of the trip.

Good luck and keep researching - I find it part of the fun!

Cindy,

1.) As Kent mentioned, Tuscany (which is a region rather than a valley) is a good place to rent a car as some of the hill towns are not as well served by public transit. However, I've found that this depends to a large extent on which towns you want to see, or whether you want the freedom to "get off the beaten track" and visit more remote locations. With most locations, I find that with careful planning I can easily get around using public transit, and often it's less expensive and faster. I tend to use rental cars just to reach specific locations, and only keep them a short time. Do NOT drive in cities if possible, especially Florence or you might encounter the dreaded "Zona Traffico Limitato" zones and get an unpleasant surprise in the mail when you return home (this applies to other towns as well - see post in this section about traveller that was "nicked" in Arezzo).

2.) Orvieto is actually in Umbria, but it's easily accessible by rail. As you're starting in Rome, take the train to Orvieto (short trip!), and then the Funicular up to the town (buy ticket in the Tabacchi in the train station). VERY easy! If you also want to visit Siena, train is also good, although you'll have to take a Taxi from the station into town. For travel from Siena to Florence, Bus is the best option. It's only a short trip (~1 hour as I recall) with beautiful scenery.

3.) Check Rick's "Italy" or city specific books for Hotel and restaurant listings and also significant sightseeing locations (along with opening & closing info, etc.). There are LOTS of choices listed!

4.) I've found the weather is generally quite pleasant in Sept. / Oct., BUT be sure to have a good rain jacket. As suggested in previous posts, "layering" is a good plan.

Note that if you do decide to rent a Car, you'll require an International Driver's Permit to drive in Italy (used in conjunction with your regular DL).

Good luck and happy travels!

I think a car is necessary to adequately explore the hilltowns. Find an agrotourismo in the area you want to visit. Take the train out of Florence or Rome (wherever you are coming from) to a town close to your agrotourismo and pick up your car. We stayed about 1/2 hour south of Siena. We picked up our car in Arezzo - rental agency was right across the street from the train station and had easy access to the highway. We were there a week and visited Siena, Montepulciano, Cortona, Pienza and several other hilltowns, and never had to drive more than a hour. We always travel in September and the weather has always been perfect.