Sorry, Ravenna should not be on the list!

How about a base in Siena and day trips to Montalcino and Montepulciano - good locations for wine lovers. Or base in Siena and visit Chianti and Montalcino.

Good advice above, but my favorite base location is San Quirico, right in the middle of Montalcino, Pienza, and Montepulciano. Look at Palazzo del Capitano for a nice hotel. That is the best of Tuscany in my opinion. See Siena as a day trip---about :45 north from SQ.

You have recognized there are too many destinations on the list. If you want a single base, prioritize whether you want to concentrate on (1)southern Tuscany (Montalcino, Pienza, Montepulciano, etc.), (2)central Tuscany (Siena, San Gim, Volterra, Chianti, etc.), or (3)northern Tuscany (Lucca, Pisa, etc.). Cortona is a bit of an outlier but could fall into a southern or central itinerary. It's a pretty drive from Montepulciano to Cortona.

When I think of Tuscan wines, I think (in order) Brunello/Montalcino, Vino Nobile/Montepulciano, and Chianti Classico. The food is great everywhere. The views are all good but very different in each part. If there are any fall colors at all in late November, central Tuscany (mostly Chianti) would be my choice.

You can visit Lucca, Siena and even San Gim as day trips from Florence using public trans. It's not ideal, but that might help you narrow your scope.

Something to consider: It will be dark by 5:00 p.m. Finding your way back (and into) a small town is easier than Siena although Siena obviously offers more dining options and evening activities.

FWIW, we were underwhelmed by Lucca although it's easy to reach from Florence by train. Volterra is very interesting but a bit far to go when time is short and the wish list long.

We recently spent a few days in Montepulciano at La Locanda di San Francesco and can recommend both the hotel and the town as a base for southern Tuscany.

I'd probably spend a few+ hours in Orvieto, arriving late in the day in Siena for 3 nights (it's worth more than a day, this way you have 2 full days there), then spend a few+ hours in San Gimignano on my way to Florence.

You may well be able to fit something else in on your way to Florence from Siena.

Orvieto and Siena are must-sees in my book. I'd check into parking issues for Siena though whether you stay overnight or just day trip by car.

Thank you for all the great advice. bobthenavigator, we took your tip and booked a suite at Palazzo del Capitano.

This is only a short leg of a rather aggressive itinerary so we view this leg as a time to relax and slow down a bit. The entire trip is as follows:

Miami to Rome (3 days)
Southern Tuscany (Montalcino, Pienza, Montepulciano) (3 days)
Florence (3 days)
Venice (3 days)
Skiing in Zermatt (3 days)
Zurich to Miami

Now that we have our home base, any recommendations in terms of itineraries, bar and restaurants are greatly appreciated.

Nice trip---I am jealous !

GOOD EATS IN TOSCANA
I have never been called “ BOB THE FOODIE” , but here are some of the best places to eat in Tuscany based on feedback from many of my clients. Reservations are suggested for most!

$=inexpensive $$=moderate prices $$$= expensive

FLORENCE:
Osteria del Cinghiale Bianco $$ Across the river & very good.
La Giostra $$$ Excellent, but you must book in advance

SIENA:
Osteria Le Logge $$ Great place for lunch and near Il Campo
Cane e Gato $$$ A fixed price & menu for a true feast—allow 4 hours

LUCCA:
Buca di San Antonio $$ Best in town and near San Michele
Il Giglio $$ In the piazza of the same name---favorite with locals

SAN GIMIGNANO:
Il Pino $$ Very good typical Tuscan fare
Le Vecchie Mura $ Good value for a tourist town

MONTALCINO:
Taverna Grappolo Blu $ Popular with locals as well.
Ristorante Poggio Antico $$ Excellent cuisine 5km south of town at winery location
Enoteca Osteria Osticcio $ Best wine tasting & small meals in town

MONTEPULCIANO:
La Grotta $$ Near San Biagio church & very good
Café Poliziano $ Great place for lunch on shopping street

Osteria Acquacheta Best bistecca in Tuscany

PIENZA: Latte du Luna $$ Best choice in this charming village

BAGNO VIGNONI: Osteria del Leone $ Good lunch choice in this spa hamlet

MONTICCHIELLO: La Porta $ Charming place with outside terrace

SAN QUIRICO: Trattoria al Vecchio Forno $ Good food & fair value

I'm also not a foodie but can add a couple of dining options in the areas you're visiting:

Orvieto: Ristorante Maurizio near the Duomo. A little too well-lit for my tastes, but the food and service were excellent.

Montepulciano: Osteria Quattro Venti facing the main/largest piazza. Simple dishes done very well; felt like home-cooked meals. Not many tables and popular with locals, so make reservations if going for dinner.

Siena: Ristorante Mugolone on Via dei Pellegrini, just a block off the Campo. A two-generation, slightly upscale restaurant (white tableclothes, waiters in tuxedos) with traditional dishes plus a few things we hadn't tried before. We enjoyed this place so much, we went twice in one week.

Florence: Ristorante Il Paiolo on Via Corso. Another family-run restaurant. Lots of locals and an all-Italian menu, but the daughter (who seems to be in charge) speaks English and will describe the dishes so well you want to order everything.

Florence: Osteria Zio Gigi on Via Folco Portinari, a small street just NE of the back of the Duomo. Very casual, neighborhood-type place, with a great atmosphere, good food and generous portions.

One thing to note - is that you will have to be very careful with the wine. Drunk driving laws in Italy are much stricter than in the US and strictly enforced. This is not something you want to do. So you can taste - but not swallow - on tours. If having wine with dinner you need to eat in the town you're staying in and walk.

(The husband of a friend was stopped for a bad taillight and when the cops realized he had been drinking - 2 glasses of wine - he was in a world of trouble. Finally got off with a fine I think just because he was an american - but it took hours to get i sorted out.)

Hi Naomi,

On my last trip, I spent 3 nights in Montalcino, a town I really fell for! I had dinner all 3 nights at Grappolo Blu. I thought it was excellent and their hearty, traditional Tuscan menu is just made for a glass (or two) of Brunello.

Loved tasting at the Fortezza because although expensive, they have a huge variety of wines and very knowledgable staff. Be sure to climb up to the walls of the fortezza and enjoy the views!

From Montalcino I drove and visited:

Sant'Antimo - mass in Gregorian Chant
Monte Olivetto - Sodoma frescos
Montepulciano - lunch at Cafe Politizano and wandering and shopping with friends
Pienza - lunch at Latte di Luna, very good

Leisurely exploring and driving around, enjoying scenery and photo ops.

These were a great 3 days!

Buon viaggio!