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Cortona, Pienza & Castellini in Chianti trip report (long)

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So many wonderful locations, so little time, but we sure explored the Cortona, Pienza and Chianti regions well. We had many positive experiences and we did our best to try many different items on the menus that I had not seen or heard of but I had to sample our favorite: Pici pasta at almost every place we stopped. There wasn't a meal that small bites of entrees weren't being passed around on forks for everyone to taste. Unfortunately, none of my clothes fit on our return but it was all worth it!

We arrived on an overnight flight from the west coast and wanted something easy close and simple to our location outside of Cortona. The first night we were guided to a local family run Trattoria in Mercatale, It would not be a destination in itself but it was a warm, friendly and jovial atmosphere for a nice price. Mimmi's Trattoria's has 2 seating’s a night and they serve the entire room family style bringing tray after tray after tray................ so much food we could not believe it: House wine from a ceramic pitcher (truly authentico), Antipasti of melon with prosciutto, 4 different kinds of pasta came one at a time (Penne, Spaghetti, Lasagna and Cannelloni all in a light tomato cream sauce), Platters of every different kind of roasted meat you can imagine, Green Salad, pecorino cheese, Dolci of Gelato. It wasn't the best cuisine of our trip but the food was not bad.......it was reasonable $$ and fun way to start:

http://www.tuscanydimimmi.it/en/Mimmi...

The next day we arrived in Cortona at 3pm, when almost everything was closing. We found Antica Trattoria a Cortona (across from Taverna Pane E Vino) in a small courtyard just off the main square. We had a wonderful warm cheese soufflé with grilled pears antipasti and some great pasta dishes including gnocchi with shrimp, tagliatelle with tuna, tomatoes and capers and a great Pici. This Pici pasta can be found all over southern Tuscany with a light tomato sauce. Wonderful!

Two evenings of this leg of our trip we chose to stay at our Inn's (Borgo di Vagli) Trattoria "I' cche c'è c'è" (whatever there is). Each night the have fixed menu/ fixed priced offering where Dina invites you in to the kitchen at 5 if you want to watch her make the pasta. The menus for our 2 days for the mere 4 or 5 tables served include antipasti of a mixture of shredded bread or faro with fresh tomatoes olives, onions, cucumbers and EV Olive oil. The first night was Hunters Chicken (cacciatore) and the next was a marvelous slice beef drizzled with boiled olive oil enhanced with Rosemary from the garden. Dolci was either gelato or fresh baked apricot torte. The wine list is also wonderful. Maximilliano (sp?) did everything he could to make the evening enjoyable and it worked!

Another evening we went to the Umbria Jazz fest in Perugia and ate antipasti and pizza in the row of outdoor cafes in the city center. All seemed filled with happy people eating antipasti or pizza. The city had great energy. You probably could not go wrong with any of them. We also visited Assisi during the day with not really a notable meal. While waiting in the city of Tuoro for the ferry to cross Lake Trasimeno, we had lunch at fun place that seems to cater to the camping and beach going crowd on the lake. Restaurante Ciao, Ciao was filled with international tourists ordering salads and grilled meats and fish. It did not seem very authentic to the Umbria region but was a fresh and tasty way to wait for the ferry. If timing had allowed, I probably would have preferred to try one of the many enticing ristorantes on Isola Maggiore.

We were ready to move on to our next location which was near the beautiful hill town of Pienza. On the way we made a stop to meander the streets in . We found a beautiful spot that had a terrace overlooking the valley. Cafe Poliziano had no room for us on their upper terrace so they escorted us down to their more formal sister restaurant's outdoor patio below and allowed us to order from the cafe's menu. The restaurant looked lovely and I'm sure would be a good place to stop for dinner (Il Grifon D'oro). I had a pepper stuffed with tuna; others had a cold tomato bread soup, another order of pici pasta and an omelet with a potato "soufflé". The colors and flavors were wonderful. The lasagna was awfully rich however.

http://www.caffepoliziano.it/

That evening we were advised to go the short drive to Montechiello, a charming Medieval Hill Town. Only 2 restaurants in the whole town and we chose the one with the terrace (La Porta) so we ate enjoying a wonderful sight of Pienza, the Val d'Orcia and we could watch the sunset over the wheat fields. A family run trattoria, we had assorted crustini and prosciutto, thinly sliced pecorino and truffle antipasti, stuffed rabbit, pici (of course) seared pork and a porcini stuffed ravioli dish in sage butter. Vin Santo with biscotti and a flan type custard finished us off with our cappuccino for desert.

http://www.valdorcia.it/osterialaport...

We had what I believe our best meal of the trip In Pienza the next evening. Il Rossellino is a wonderful, quaint, 4-5 table, mom and pop restaurante with warm, friendly service and exquisite cuisine. We felt as if were were invited into someone's home for dinner. We were offered complimentary glasses of Prosceco as a welcome. My husband and I again chose to share many courses and I have no idea how anyone could eat the entire course of food on their own. Each bite was a feast. Our host showed us the cuts of beef for our Bisteca Fiorentina (the best we've ever had) to choose from. Each dish from antipasti to dolci was a treat.

The next day, on our way back from the Montalccino we visited the Sant'Antimo Abbey to hear the Gregorian Monks chant (unbelievable ... a must visit) and stopped for a fabulous lunch at The Fattoria dei Barbi winery. We tasted and took a short tour of one of what might be considered the oldest and most respected wine producers in Italy. They offer an elegant lunch in their Taverna and we were advised that the full tasting menu would require a few hours but is quite wonderful. We assumed that it might suit better for an evening meal so we ordered a la carte. We chose servings of crustini and a wonderful thinly sliced eggplant stuffed with warm cheese. We again had to try the Pici, this time served it was offered with porcini mushrooms. Our friends enjoyed their grilled veal and lasagna. We had to pair the meal with the wineries wonderful Brunello, the highlighted wine of the region.

http://www.fattoriadeibarbi.net/eng/t...

The last dinner in southern Tuscany was at the sleepy, walled "Spa" town of Bagno Vignoni. The center of town is an Etruscan hot springs pool. The town was empty but Osteria Del Leone offered a casual but elegantly prepared meal in their outdoor patio. Antipasti included Fresh Tuscan Tomato, bread and basil soup; thinly slice cold duck drizzled with basil olive oil and Carpaccio of zucchini with Tomino cheese and pistachio nuts. Our friends had Loin of Pork cooked with fresh button mushrooms and Rabbit cooked in an orange and almond sauce that were wonderful.

http://www.illeone.co.uk/osteria_del_...

We then moved on to the Chianti region. Our hotel, just outside of Castellina in Chianti afforded many different locations within a 10-15 minute windy drive. Just outside of town was the best and most popular Gelateria in the region…it was always overflowing with people. We had a few non-notable dining experiences (for ex., Pizzeria Tre Porte is one I would definitely avoid for we experienced very poor service and then heard multiple reports of mediocre food). In the quiet hill town of Volterra, we found a beautiful terrace for lunch overlooking the valley at Dietro Le Quinte. The menu provides Tuscan specialties, freshly caught fish, home made pasta, original and creative dishes with genuine and fresh local products. The menu changes with the changing seasons. We had delicious green salad with fresh fish, a variety of pastas (pici, a salmon, dill and a light Bolognese). It’s a challenge to find but venture through the entrance into the magical garden situated along the medieval walls of the town.

http://dietrolequinteristorante.it/di...

Another day’s lunch stop at the abbey/winery/restaurante, Badia a Coltibuono; we were rewarded as we sat under a vineyard arbor with a gorgeous views across the valley. The cuisine was equally gorgeous with a Caprese salad, Salt cod-fish, tomato with olive pesto sauce and homemade pasta with wild boar. This was definitely worth the stop since it was the Coltibuono monks who were the first to plant Chianti grapes in this region in 1051. Unfortunately we did not have the opportunity to taste or take a winery tour other than what we purchased with lunch. I hear their cooking school is also wonderful but very pricey.

http://www.coltibuono.com/0ristorante...

The second best meal of our trip was on our last evening and was recommended by a fellow hotel guest who visited this restaurant twice. La Perla Del Palazzo in the town of Radda in Chianti served a delicious caprese salad and Pasta fagioli in addition to wonderfully grilled beef, veal and interesting pastas.

As time moves on, my memory of some specifics are beginning to fail me so I guess I will have to return soon to re-live the details I've lost. Tuscan cuisine is wonderfully rustic and different than any other region in Italy.

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  1. Thanks for the trip report. We'll be staying in Castellina in a few weeks, so your report is particularly useful.

    1 Reply
    1. re: more of everything

      Believe it or not...there are restaurants in Castellina not mentioned above:

      "Antica Trattoria La Torre" came highly recommended and was very, very crowed (turning away guests w/o reservations). It was quite good but did not WOW us the was some of our other locations did. Maybe it was us??

      We also went to a casual Pizza place out of town on the road to Gretole which was an outdoor patio "on a lake" (a buggy, fishing pond was what it really was). It was casual and had pretty good pizza. It was filled with locals but they're oven could only cook 4 pizza's at a time and everyone was getting frustrated with them. Not worth wasting a night but if you are in the area......

      Other guests at our inn said that had the finest meal of their many trips to Italy at:

      http://www.gallopapa.com/home_eng.htm

      We did not go there so I could not include it in my report but I thought I would pass it on. It's a prix fix menu and quite expensive but according to them, totally worth every penny.

    2. Interesting. We stayed in one of the villas at Fattoria Barbi several years ago and enjoyed the tour and dinner.

      More importantly, I share your enjoyment of Il Rossillino. When I ate there a few years ago my entree was one large porcino cap sauted in butter and thyme. Unforgetable.

      1. OK...funny story:

        We put a lot of planning into this trip, collecting ideas and tips from many sources. We are usually pretty good at this sort of thing. A friend who had just returned from his honeymoon told us that he just spent 7 days in Volterra and it was a city not to be missed so we added it to our itinerary.

        While gathering the info to put together this trip report, I had a hard time remembering the name of the beautiful restaurant we visited in Volterra. All the online research I could do proved fruitless. I finally found the card for Dietro Le Quinte, finished the story and posted it.

        Now, I've noticed, looking at the business card and the website, that it did not mention Volterra anywhere. And no-where on Volterra's pages was the restaurant listed. I was perplexed!

        I've now come to realize, that even though we thought we were there.....we never made it to Volterra! This restaurant was in another walled hill town altogether!!! Colle Di Val D’Elsa is a beautiful but small town situated on the road to Volterra. It took my research for Chowhound to figure this out!!!! We did not know this until 2 weeks after our return!!!!

        I guess when I think about it, even at the time, I was equally perplexed, on how our friend could spend 7 days in this very small, quiet town. The restaurant is definitely worth your efforts if you are in the area though.

        Now, the desire to actually reach Volterra will be another reason for us to re-visit Tuscany again!

        1. Thanks for this report -very interesting (and detailed!)

          1. Cortona has a lovely little chocolate shop--I can't recall the name, but I enjoyed chocolate dipped figs, orange peel, hot chocolate, and a variety of mini pastries, as well as good cappucino & espresso. It's on one of the main streets--if you park in the town lot outside the walls and head to the piazza in the middle of town, you walk right up this street.

            1 Reply
            1. re: Hungry Celeste

              To clarify my ridiculously vague previous post: the choc shop is Cocoa Cortona, located at via Guelfa, 45. www.cocoadolceria.it

            2. Pienza is the donkey's pl....r but Il Rossellino is the worst restaurant there. Take a look at my trip report for recommendations.

              Buon Natale a tutti.

              1. Returned recently from a European vacation that had me stopping in Cortona for a couple nights. My wife and I had one of the best meals of our lives at Dolce Maria. Maybe it was the 6 hours we had just spent on the Autostrada or maybe it was dining al fresco and eating tagliatelle in oil with shaved truffles. Entire meal with a bottle of wine was under 60Euro. Highly recommend if you're in the area.

                http://www.tripadvisor.com/Restaurant...