Hi everyone,
We are flying into Milan on a Tuesday for a week. We were going to go to the Lake Como region, but changed our mind and decided on Tuscany instead. We are going to take a train to Florence the first day in, then either stay the night or rent a car and drive to Tuscany.
We only have 5 full days, any recommended itineraries?

Thanks in advance

If you are going to Florence you are already in Tuscany. Florence is the Capital of that region.

That's true, thanks.

as has been said, if you are in Firenze, you are in Tuscany. So, what do you wish to do in Tuscany? I would recommend hiring a driver if you want to maximize your ability to relax and enjoy the scenery....or utilize public transit such as train/bus to get about. Why hassle with renting a car, gas, tolls, unfamiliar roads/traffic laws, having to park,pay for parking, returning the rental,etc. etc.

What time of year is this trip?

Yes, what time of year and where do you egress?

Its next week, Sept 1-7. Not sure what to do, we can do Florence as a base and do day trips from there? I was looking at Siena and Lucca. We can rent a car, but I couldn't do a private driver.

Next week?...wow, I'm way to anal to not have plans worked out a week before I leave. That said, you could very easy stay in Florence for the duration and day trip from there. Arezzo is an easy hour by train and Siena the same by bus. The bus, not the train to Siena - you get dropped off right in the historic center. You can also visit San Gimignano. Where are you flying home from? Are you planning on making hotel arrangements prior to arriving in Italy?

Yes, Florence doesn't make a good base for daytripping by car. (By train you can go to Pisa, Lucca and Arezzo, by bus Siena and Fiesole.) Which part of Tuscany do you want to see? The favorite on this forum is southern Tuscany, which is where most of the tourism photos are taken. Southern Tuscany is good for car touring with a base in Pienza or San Quirico d'Orcia.

Get to Florence ASAP and get your car when you can---hours they are open---and stay in one of these:

BOB’S FAVORITE DIGS IN TOSCANA

A. RURAL LOCATIONS: All have parking and good food options nearby

1. Relais La Saracina www.lasaracina.it 230 to 300E
Fabulous country home near Montepulciano—helpful owners

2. Cretaiole Agriturismo http://www.cretaiole.it/ Good value for families

3. Terre di Nano www.terredinano.com 100 to 155
Both rooms and apartments at rural Agriturismo near Monticchiello


4. Casanova di Pescille http://www.casanovadipescille.com/ 100E
Rural B&B 3 KM from famed San Gimignano—we loved the views of San Gim.

5. Fattoria Tregole www.fattoria-tregole.com 110E to 180E
Has both B&B and apartment accommodations. Near Castellina in Chianti

6. Agriturismo apts. near San Quirico— www.poggiolo.info/ About 110E

B. IN-TOWN LOCATIONS: For walking convenience to shops & ristorantes.

1. Palazzo del Capitano www.palazzodelcapitano.com 130 to 180E
Very nice small hotel in center of San Quirico—perfect location to explore.

2. Vecchia Oliviera www.tuscany.net/oliviera/ 130 to 180E
Nice 4 star hotel at the gate into lovely Montalcino---has pool.

3. Palazzina Cesari www.montalcinoitaly.com 80 to 110E
Lovely small B&B in heart of Montalcino—great value—2 night stay minimum.

4. Locanda di San Francesco www.locandasanfrancesco.it 180 to 200E
New boutique B&B in a lovely location in Montepulciano—great reviews !

5. Politian apartments http://www.politian.com/ Good value apts. with
minimum stay of 3 nights in Montepulciano---helpful host---85E

6. Palazzo Ravizza www.palazzoravizza.it 130 to 180E
Very nice & popular hotel in Siena with parking.

7. Fattoria Vignale http://www.vignale.it/eng/ Four star hotel in Radda in the heart of Chianti. About 230E for double

I think you need to nail down lodging reservations. That may determine where you end up exploring.

ilovetravel,
See http://www.slowtrav.com/italy/tuscany/hs_planning.htm

Thanks everyone!