Tuscany Bound (looking for recs)

All you Italy lovers,

Could you help me with some suggestions for what to see/do/eat while in Tuscany for a week?

We’ll be renting a house in the heart of Tuscany, almost exactly midway between Florence and Siena. The name of the town is San Donato in Poggio. We will be traveling at the end of June 2022. Interests are food, wine, and medieval villages.

Any good restaurants near by? Suggestions for wineries to visit? If I could save up calories in advance, I would. I have a feeling I’ll be gaining some pounds on this one.


Well, you’re staying in a medieval village! We visited in September while staying in Siena just to get an appreciation for how a small medieval village operated - all the features of Siena on a much smaller scale. I can’t help you with food and wine since we were just passing through. Have a great trip!

Hi Daniel- tons of great threads on trip suggestions and trip reports if you search Tuscany. Interesting location and looks to be in Chianti country. Are you going to have a driver any of the days ? Is Florence in play ?

A couple of no brainers for me would be visiting Isole Olena winery. Looks like they’re very close to where you’re staying. They don’t seem to have a website but you can find their number to call and set up a visit. Their Chianti and flagship wine Cepparello are excellent. You should be near some other good Chianti choices.

Arnolfo is a Michelin 2 star restaurant in a small village about 25 minutes away. That would be a great lunch or dinner option depending on your schedule. Your about 35 minutes from San Gimignano. It’s one of the favorite tourist towns and Cum Quibus is there and excellent.

Your about 90 minutes to Montalcino. I’d definitely hire a driver for a day (if your going to taste). Plenty of wineries to visit or you can visit 2 great Enoteca’s in town which we did and taste a ton of wine. I’d highly recommend either having lunch/dinner or doing the cooking school experience at https://montalcinocookingschool.com/ Locanda Demetra. Terrific family and really good local food with amazing views. If you want to do a winery visit the lunch and tour at Col d’ Orca is excellent.

They’re are a ton of threads on Florence. If your going make sure to visit Enoteca Pitti Gola. It would be a good option for a light lunch and some amazing older Chianti in between seeing the sights.

Here is my trip report from Sept. We hit Florence and Montalcino. Plenty of pics on the thread https://wineimport.discoursehosting.net/t/italy-trip-report-positano-rome-montalcino-florence/173548/1

Towns: San Gimignano, Monteriggioni
Wine: Tenuta Villa Trasqua, La Sala, Terre di Perseto (lowkey favorite), Conte Guicciardini, Antorini (if only for the design/architecture)

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Not much I can offer specifically, except noticing Colle di Val d’Elsa is in very near striking distance, I’d definitely recommend it. We day-tripped there and found it charming, relatively untouristy (in the general Tuscan scheme of things), and it also helped that we found a small and understated trattoria/bistrot type place that was friendly and had some good wild mushroom dishes. Sorry I didn’t take down their name.

I like the idea that you’re staying in a small rural (and historic) location, ideally situated to visit wineries, but nonetheless with Siena in easy reach. The sort of positioning I like.

I visited the tiny town of Monteriggioni and had a delightful lunch at Ristorante il Pozzo. Very quiet place, relatively. Another unknown, closer to Siena is Ristorante Pizzeria La Botte Del Chianti. Its NOT a pizza place; ate there several times. Friendly, excellent food, if a bit slow occasionally. You actually need res many nights. Popular w/locals.

il Pozzo is now called le Torri Monteriggioni and I can second that recommendation.

We stayed in a villa outside of Greve in Chianti. It was gorgeous. A highlight was there was a mulberry tree that two badgers would come visit us every evening. We also saw pole cats in the trees. At one point I was watching otters on a bridge behind Enoteca Falorni, at sunset, and eating strawberry gelato; doesn’t get better than that. When I go again, I will try to stay within walking distance of Montefioralle.

Ristorante Albergaccio of Castellina in Chianti was a highlight of our trip. Our favorite winery was Felsina, but Verrazzano was wonderful too.

A recommendation that was off the beaten path was the Etruscan Road San Rocco in Sorano. Stopped by Montalcino on the way down and Terme di Saturnia on the way back.

I personally liked Cortona and Lucca more than San Gimignano. The Wednesday morning market in Fortezza Medicea in Siena is worth seeing. Hope that helps.

You are about 1 hr from a working monastery, Abbazia di Monte Oliveto Maggiore. We had a lovely experience; tour the facility an hour+ before closing, have a nice tasting of house made olive oil and decent wine, then stay for the vespers service.


we’re scheduled to visit them in June!

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15 minutes drive from you will be Castello di Monsanto and Castello di Fonterutolli (Mazzei). They are welcoming with their wine visits, by appointment only.

We had a wonderful tour and tasting at MastroJanni. We had a driver because it’s extremely hard to find.

La Toppa in San Donato (Traditional)
La Galleria in Poggibonsi (seafood)
Bule in Bargino (traditional)
Arnolfo in Colle val d’elsa (2 michelin stars)