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Tuscany in the end of Sept/Oct: Pienza, Montalcino, Siena, Castellina

6 days of biking: Pienza (2 nights), Montalcino, Siena, Castellina (2 nights). This will be our second trip to Tuscany, however more time focused in the triangle between Castellina, Pienza and Siena. Will not have a car but can manipulate our routes for better lunches. Last time had a magical night at Lamole di Lamole up from Greve, will need to return if only for the memories.

Lunch targets include:
Monticchiello
Montepulciano
Monte Oliveto Maggiore
Castelnuovo Berardenga

Though we're happy to manipulate the rides to get to better chow.

They've recommended Cane e Gatto in Siena

We'll follow the thread for the last three days in Rome which was just posted.

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  1. I heartily recommend La Bottega del 30 in Castelnuovo Berardenga. We had a wonderful tasting dinner there in their charming garden and the hospitality was top-notch!

    1. There are a few very nice places in Pienza.. not fancy but great home cooking. The one I remember most is Latte de Luna (hope I got that right). If you want an extraordinary meal, visit La Chiusa in Montefollonico. It's between Pienza and Montepulciano and is also a small hotel. The lunches and dinners are very special.

      1. A couple of 20 yr old reccs - The restaurant at the "castle" at Monte Oliveto Maggiore was pleasant - dont omit visiting this site, the landscape is staggering and the frescos are great.

        Fattoria Pulcino outside of Montepulciano, casual and relaxing - when I really need comfort food I try to reproduce their fire-toasted bread with garlic and delicious olive oil poured over.

        If you get up in the area of Monte San Savino, the Gargonza fort is lovely and they have a pleasant restaurant with wild boar, roasted meats, oil and wine from the estate

        Be sure to buy some new oil on this trip - there should be some fresh new oil being pressed by the time of your visit. Also, if the fall rains have started, there should be mushrooms on the menus along with game, delicious fall fruits, muscat grapes, pears, etc.

        Lastly, I believe there has been a lot of new restaurant and lodgings developments in some of the smaller, non-destination towns in the center of your area -im thinking about places like asciano, buonconvento, lucignano, etc. Because it has another focus on Tuscan villa rentals, you might want to check the slowtrav website which has some restaurant recommendations in this area, http://www.slowtrav.com/italy/restaur...

        as well as the slowfood website.

        Enjoy, and looking forward to your report back.

        1. Stop by the lovely village of Fonterutoli (just outside Castellina) and definitely book a dinner at the Osteria there. It's a tiny village w/ 2 streets, 1 town square, and this little restaurant cum general store and bar run by 2 brothers. The food is home cooked and outstanding, the veal or steak w/ truffles is to die for, never will you have truffles like that again! And it's a really friendly, homey place. We stayed in a small house in the village several years ago and had a couple of meals at the Osteria, and they even brought over warm plates of food for us one night b/c the kids were crashed out and we couldn't get out. Also, the olive oil is fabulous and the brothers can sell you a bottle (very hard to find in the U.S., we've tried) as is their Chianti, but they are known for their olive oil. Enjoy!

          1. I don't know what their hours are in September, but in the Spring, the abbey of Monte Oliveto Maggiore is only open to visitors before noon. (If we hadn't blended in with a school group this last year, we would've missed out on the exquisite frescos for a second time.) In any case, you might want to schedule lunch for after your visit.

            1. We had a lovely lunch at Papei Trattoria in Siena just down the hill behind the town hall.

              1. Ristorante Nello La Taverna
                Via del Porrione, 28 SIENA

                1. Whoa, what a coincidence. I just got back from Italy and one of the best meals we had (actually two, since we went back) was in Monticchiello. I had to poke around a bit just now to find the name, but I'm pretty sure the place is called Taverna di Moranda. It's right in Monicchiello. It's up the main street on the left and the back room has a low vaulted ceiling. It's a tiny town, so it won't be hard to find once you're there. It was procini season when we were there and the Porcini al Forno was a nearly life-changing experience. The pici is also highly recommended. It's closed Fridays, I believe.

                  1 Reply
                  1. re: celeriac

                    Taverna di Moranda is pleasant, but if you are in Monticchiello
                    just long enough for one meal (and unless you're going for the
                    midsummer theater festival, you probably will be), you should
                    probably go to La Porta, which is one of the best restaurants
                    in this part of Tuscany, instead. Very good hand-rolled pici,
                    plenty of truffles, great roast meats and game (I love the
                    stuffed pheasant), and a wonderful winelist filled with under-
                    valued vintages from Montepulciano and Montalcino. If the
                    weather is warm, the view across the Val d'Orcia from the
                    terrace is stunning.

                  2. If you are in this area - try to make Montepulciano. There are several outstanding restaurants here. Our favorites are Acquacheta and Trattoria Caragna. Acquacheta is family run and Paulo and Giulio are too much - in the traditional Italian style, you will probably share table with others. Caragna is run by Il Sasso, an Italian Language School in Montepulciano - again, wonderful people and some outstanding food.