The places you have noted are all nice but they are in Chianti and not my favorite part of Tuscany, which is further south. Here are some more options. Look first at Terre di Nano and do not miss the bargain at Santa Anna in Camprena.

have fun---hard to go wrong:


BOB’S FAVORITE DIGS IN TUSCANY
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
Isabella also has 2 apts. in Castelmuzio for rent—wonderful—see her site.

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

7. New historic B&B north of Pienza. http://www.camprena.it/index.htm
Site of filming for THE ENGLISH PATIENT About 90E for double

8. http://www.borgoargenina.it/index.html A special rural B&B in Chianti.
The lovely owner, Elena, will make you feel like family. 170E for double

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

1. Palazzo del Capitano www.palazzodelcapitano.com 170 to 210E
Very nice small hotel in center of San Quirico—perfect location to explore.

2. Vecchia Oliviera www.vecchiaoliviera.com/ 150 to 200E
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 170 to 250E
Very nice & popular hotel in Siena with parking.

Were you planning to explore part of Tuscany from this base, or just relax, take a cooking class, and enjoy where you are? Tuscany is huge (9000 sq. mi.), and there are lovely properties in many parts of the region.

We would like to use it as a base I think. I am honestly not that sure what I want to see yet. I think we will want to explore some of the winery's and towns in the region, enjoying the cuisine. Recommendation's are welcome.

Also, thank you Bob for the recommendations!

On the other hand, we prefer Chianti and it's greener landscape but you can't go wrong. Look at places you want to visit on day trips and then choose a location to stay in.

CK27,

Are you looking for a place to stay that also offers cooking classes, or are you willing to drive to the class?

You might take a look at reviews of 1-day cooking classes on TripAdvisor, and see what appeals to you. It might help you zero in on a geographic area that is near one of the places being recommended to you (and you should read reviews of anything before you book it).

It may *sound* crazy, but the very loose plan you have for enjoying Tuscany is really the best way to enjoy Tuscany, no matter if you choose the Chianti or the val d'Orcia. When people rave about Tuscany, it is not because they saw X town on a daytrip. It's because they drove around without too strict a plan, let the day flow, ate long, long lunches, stopped on a whim at some town they spotted that looked pretty, drank the local wine.

So while in the end you will have to make some choices, don't over-worry the location if the hotel or farm lodgings really looks perfect for you (the rooms, the pool, etc.) Tuscany is just overflowing with beautiful drives, atmospheric towns and castles, and loads of good wine and taste treats. Pick any spot in the wine country and everything will be at your door step.

By the way, the place that was recommended to you by your aunt, Le Ragnaie, is NOT in the Chianti. It is located right near Montalcino in what I consider the single most beautiful part of Tuscany. (We all have our favorites!).

Best of all, Le Ragnaie has a restaurant, which means that you can come "home" to a dinner and drink all the wine you wish without worrying about needing to drive again. Le Regnaie is actually a winery as well as a farm stay, and they make their own highly regarded Brunello, the star wine of Tuscany:

http://www.wineaccess.com/wine/product/11187410/2005-Le-Ragnaie-Brunello-di-Montalcino

If the rooms don't appeal to you or you like someplace else better, you shouldn't stay there (and you should of course read reviews on TripAdvisor). But complimenti to your aunt for a worthy suggestion!

You either pick the lodging and then figure out what's within range for exploring -or- you decide what you want to see/do and then pick the lodging that is geographically central.

Are the 5 days in Florence/Tuscany your entire trip? What airport(s) are you flying into and out of? Picking up a rental car IN Florence can be a little tricky, so tell us the rest of your plans. We may have logistical suggestions.

Thanks everyone for the suggestions! It is so helpful.

So we are doing quite a bit, which I know most people are against, but to each their own as I like to say, so lets not focus too much on that part of my itinerary.

We will be departing from Boston and the trip will be as follows:

4 Nights Santorini
2 Nights Florence
3 Nights Tuscany Hills
3 Nights Rome
4 Nights Positano (was potentially considering Ravello instead but not sure if it would be too far removed for that many days)

I still need to figure out where we will pick up the rental car out of Florence, need to do some research.

How are you getting from Santorini to Florence? I'm guessing that will take an entire day and involve multiple segments, so you'll only have one full day in Florence. Will that be enough time to see what you want to see? Depending on what day of the week this is, you might have trouble seeing some of the main sights.

You might consider skipping Florence entirely. Fly into Rome, pick up the car at the airport and drive to your Tuscany base.

And where will you fly out of Italy? You'll need to be within a reasonable distance (with good transport options) to that airport on your last night. You could hire a driver to take you to the Naples airport from Positano, but that's fairly spendy. Depending on the flight time, public trans might not be an option. If it's the Rome airport, you can get there quickly from the Naples train station (2 hours), but you have to travel from Positano first. It's a risky plan to rely on the trains to take you that far for a departing flight, and it's not something most of us here would recommend. Too many opportunities for delays.

Have you figured out how to get to Florence from Santorini? To smooth out the travel, I would rearrange the itinerary as follows:

Santorini
Rome
Positano
(Pick up a car and drive to Tuscany)
Tuscany
Florence

All very good feedback we hadn't considered.


What if we do the following instead:
Positano
Tuscany
Florence
Rome
Santorini

Then we could fly out of Rome to get to Santorini. And getting to the airport in Santorini would be much easier.

Thoughts?

Although, I guess the question is then, how do we get from Naples Airport to Positano when our flight arrives at 6pm?