Tuscany Recommendations?

Will have about 4 days to enjoy time around a business trip in Rome. Never been before, looking for recommendations on places to stay, things todo, places to eat and wineries to visit. TIA!

Bumping - going to be there in early October, if that makes any difference.

Hi Jud
What appeals to you?
For easy but good wine focus, Montepulciano has wineries in the classic hilltop town.
Florence has art and architecture and attracts many tourists
Siena has class, though I found a certain aloofness about the place
Pisa is remarkably ‘under the radar’. That may sound crazy with the field of miracles being such a major tourist destination, but all too many see Pisa as a half day experience. The area around the field of miracles is tourist tatty, and the routes from either station there are also to be avoided for this tat and ripoff cafes. However the 5 min walk to the city proper reveals a proper town with good food fairly priced, a decent market, and better farmers market. The churches are worthy of investigation.
Lucca gives you another place where you can stroll around easily, has a couple of very interesting wine shops
Plenty of other options.

Thanks Ian - after some more research we are actually thinking about a couple of days in montepulciano and then a couple of days in Florence before taking the train back to Rome. we have an agrihotel that a friend recommends highly in Montepulciano, but would welcome any recommendations on Florence. would also love any winery recommendations while in Montepulciano - Italian is very limited, so at least some English would be helpful for a cellar door visit.

Hi Jud
For Montepulciano
Although I always aim to speak Italian (not always very well), there seemed to be a reasonable amount of English spoken, and is often a useful shared language for Germanic visitors who seem to speak English more than Italian.
I really liked Crociani wines before visiting, but it was still a very welcoming shop, despite them being knew deep in packing boxes. Making an appointment may have helped (they were pleasantly surprised I did), but the ladies there just seemed to be hard-working and hospitable.
Contucci might be worth a visit. Despite being focused towards visitors rather than retail, they apparently do a good job of it. We also visited a lovely little family winery out nr Montepulciano Stazione (out the back of Poliziano which I found a little commercialised). Daviddi is the little place. Not worth a journey out on it’s own, but one of the warmer welcomes we received (we did book). Good wines priced very fairly.

Here are the basic notes I made before going, and unlike normal we actually visited a few of them (a day listed = closing day. Strikethrough never pastes correctly):

Local taxi: Emanuele Torelli (0)335 6177126
Tourist office – Piazza Don Minzoni mon-sat &
strada del vino – Piazza Grande 7 mon-fri (closed Nov-Mar)
tra in bus to Siena
A Gambe di Gatto - Via dell’Opio nel Corso, 34, Phone: 0578.757431 (good food) wed
Ai Quattro Venti - Piazza Grande, Phone: 0578.717231
*Borgo Buio - Via Borgo Buio 10, Phone: 0578 717497 mon
This place is probably a love it or hate it experience, as the owner is an opera fan and loves to serenade guests. TBH I was less towards the love it side, but we bumped into a charming Austrian couple we’d met earlier, so it was great to have a little more time with them, and the food was fairly good.
*La Grotta - Localita’ San Biagio, 15, Phone: 0578 757607 wed
I thought this place would be touristy, being opposite San Biagio, but service was slick and the food was tasty and quite classy. Maybe low expectations helped, but really enjoyed this - it felt like a ‘fine’ meal.
Osteria dell’Acquacheta - Via del Teatro 22, Phone: 0578.75.84.43 wed-mon

  • Osteria del Conte - Via San Donato, 19, Phone: 0578.766.062 wed
    Slightly out of the way, at one end of town, but all the better for it. Honest food in an fairly basic setting with decent wine selection. The simplicity making the whole more than the parts.
    Ristorante Le Logge del Vignola - via delle Erbe, 6, Phone: 0578.717290
    Cafe Poliziano – via di Voltaia nel Corso 27
    Breakfast seemed poor value/uninteresting, but so often Italians don’t take this meal seriously (there is always better to come). However it was a great afternoon venue for a coffee and a selection of their mignons/small cakes on display.
    Trattoria Diva e Maceo - Via di Gracciano nel Corso, 90/92, Phone: 0578.716.951 tue
    Caseficio Silvana Cugusi, via della boccia 8 (cheeses incl. Pecorino)

No Florence info, but Florence advice for their should be easy to find as so many visit it.

Thanks Ian - very helpful…

Jim Dietz was there in May. He may be busy having cocktails after his morning beers though.