Siena?

The city or the Province?
The city can be seen in a day---the Province may take a week.
Do you plan to stay in the city? Will you have a car? What is your budget?

Oh my! My inquiry is prompted by friends' saying in response to "where should we go": "go to Siena" I am assuming they are referring to the city as our time is limited. I don't think we would want to spend more than $150USD per night (and are always open to a bargain, so we can by more wine and gelato! As long as it is clean and in a safe area, we are fine. We will have a car, but enjoy travelling by train. Our "homebase" for our trip is north of Milan, on the west side of Lago Maggiore.

Siena is a perfect base, and probably our favorite city in Italy. The city itself can be explored in a day or two, but it is also great for wandering around in the evening (note that the streetlights are marked with the colors of the contrada you are in), and you are rarely more than an hour from any place you would want to day trip to. No traffic inside the walls, so great for walking (not so good if you have a car, though, because you probably have to park it outside the walls). Nice restaurants in just about any price range, and the most beautiful Campo in all of Italy. The last time we were there we didn't do much sightseeing in the city itself because we had already done the churches (yes, including the one with St. Catherine's head), but we used it as a good base for exploring south of there (day trips to Montalcino, Montepulciano, Pienza, etc.). We were there last September and the weather was still a little bit warmer than we expected, but by October it should be perfect. Because of the restrictions on traffic inside the walls, it is much "calmer" and more pedestrian-friendly at night than Florence is.

As bobthenavigator points out, you couldn't see all of Tuscany in three days, but staying three days in/near Siena with a car would be very nice. Other posters here prefer the Val'd'Orcia area in southern Tuscany, and I like the Chianti area a lot. There are no "wrong" areas in Tuscany.

I have spent just over two months in Siena over the past couple of years, and I cannot think of any "unsafe" areas - certainly not within the walls. This view was echoed by the many young female students I met - who all said they felt perfectly safe in the city.

You can certainly do the "highlights" in a day. For me, they were the Duomo (certainly in my top 3 of any I have visited in Italy), the climb up the torre del mangia (it is over 400 steps, but the view is worth the climb) and just wandering the streets finding the different fountains and churches of the Contrade.

I would probably allot two days to Siena proper because I only spent one day and night there and it wasn't enough for me. I wanted more time just to wander and relax. I liked it because it's not as pokey as smaller towns. But then others prefer smaller towns--really just depends on your taste and interests and what you want to do on your holiday.

Have a great trip!

Siena lovely-see my trip log on Tuscany for the Sienna restaurant with fabulous wild boar and the endless street parties for the winning neighborhood of the Palo race.
Jolly hotel nice there. Also be sure to visit the Enoteca around the corner of the Jolly hotel

lacoquine,
See the campo where the palio is run.
Palazzo Pubblico, town hall, has Sienese art including Ambrogio Lorenzetti's Good and bad Government.
Climb the Torre di Mangia for a breath taking view of the city.

The duomo is has a great exterior and is filled with works by Donatello, Bernini, Michelangelo, and Pisano as well as containing the Libreria Piccolomini. Even the floor is covered in art.
The bapistry and crypt are beneath the Duomo.
Spedale di Santa Marie delle scalla is a 1000 year old hospital that has huge works of art.
The archaeological museum under the hospital.
Museo dell'Opera del Duomo.

The above is only part of what you can see in two of the piazza. There is much more.

Budget hotels include Alma Domus and Cannon d'Oro. Both inside the walls.

Restaurants are numerous. I like La Finestra and Papei behind the town hall and Bagoga by Santa Caterina.
Others will tell you they like Cane e Gatto, La Torre and Osteria Le Logge

Henry

I have stayed in Siena several times. Most recently I stayed in a hotel in a residential/commercial area just outside the walls. I had a car and parking was convenient to where I stayed. We visited both in Siena and nearby using the car. We also spent one long day in Florence. Rather than driving we got up early and took the SITA bus. (I had in the past driven to Florence during the business day rush hour and didn't relish that thought again.)We took an evening bus home following dinner. We returned to the Campo that evening for a wine. It is a great piazza.

I highly recommend this b&b located in the heart of the city of Siena-

http://www.residenzadepoca.it/index.php

The rooms are beautiful and the rates a bargin.

Grazie to everyone! I am very excited about visiting Siena..sounds like a good homebase.
jed72, how long is the SITA busride to Florence?

lacoquine,
Siena to Florence see http://www.sitabus.it/sita-toscana/Firenze-Siena07.pdf

If you drive to Siena, park at the train station - well marked, with a large underground parking lot - walk across the street and take the bus into the centro storico. It is a lovely city - well worth a day or two.

I was very pleasantly surprised by how much I liked Siena last year and how much I preferred staying there to staying in Florence, which I had loved many years ago but found mostly unpleasant now.

I recommend staying at the Palazzo Ravizza, www.palazzoravizza.it, which is within easy walking distance of the main places of interest and a choice of good restaurants. The rates in October seem to be within your budget and there is parking available in a lot behind the hotel, within the walls of the city. The rooms at the back of the hotel have a stunning view of the surrounding hills and the lovely garden.

Here are some of my photos from that trip: http://www.flickr.com/photos/objetsparis/sets/72157605709805514/

The last photo is the view from our room at Palazzo Ravizza

The bus takes about an hour if you take the rapido and has departures almost hourly except on Sunday. There's also a bus that makes stops and takes a bit longer.

We took the bus to Siena from Florence and spent half a day there and then took the bus to San Gimignano and spent the other half of the day there...2 beautiful places to visit.