Italy: Pienza, Montechiello, and Montalcino

This whole post could be pictures of sunsets and vineyards and it would accurately describe these couple of days in Tuscany. As we looked out the car window we kept saying, Wow, and, Man, that is beautiful! Tuscany was not short on stunning views, yet we never felt immune to its charms and beauty. The golden hour and sunsets? Simply stunning.

One thing I really liked about this trip was our relatively loose itinerary. I knew there were a couple of hill towns I wanted to see in the area and we all knew we never wanted to feel rushed, so visiting one or two towns a day felt very reasonable. We would sleep in, make scrambled eggs and coffee, ease into the day and pick a spot to visit over breakfast and reading. It felt spontaneous and relaxed but still productive. Of course we wanted to “see the sights” but taking our time and indulging in quiet mornings was just as much of a priority on this vacation.

Pienza was recommended to us and lucky for us it was only 20 minutes away from Montepulciano by car. It’s a very small town that is overrun with tourists on the weekend so we were happy to find it only partially full on a Tuesday afternoon. Pienza is home to pecorino tuscano cheese so be sure to set aside some time for tasting in the local cheese shops.

The alleys and streets are picturesque and dotted with novelty shops and cafes. We opted to walk around the little cathedral and grab a couple beers at the Tabacchi in the main square and people watch. We also had some really delicious gelato here…

After buying cheese and salami we got back in the car and headed to Montechiello, which is about 30-40 minutes away from Pienza. I know measuring distance in time sounds a bit obtuse, but those roads! They’re so windy and there are so many little routes you could take that I could never keep track of it all. If you tend to get carsick, as I do, keep a steady constitution and your eyes on the road.

I had read somewhere that Montechiello had beautiful sunsets and it certainly did not disappoint. We walked around the teeny village, bought a little souvenir, and grabbed an aperitivo from a wine shop outside the city walls for the sunset.

Right inside the walls is a well-known restaurant called La Porta (by the way, I noticed that almost every town has a restaurant called either La Porta or La Grotta; sometimes both). We were unable to get reservations the night before but snuck in this night and boy am I grateful. It was our favorite meal of the trip and a very memorable night. The service at the restaurant is wonderful and we felt very well taken care of. They have a phenomenal wine list, and might I suggest treating yourself to something special and unique? I’d highly recommend making the sunset and dinner a part of your itinerary. Booking essential.

Attenzione, ladies! Phil likes running, skiing, cool music, good food and wine, and the Kansas City Royals, among other notable pastimes : )

^^La Porta (you could snag those outdoor seats if you’re lucky!)

Wednesday was our major chill day. We slept in blissfully late, cooked breakfast, wandered around Montepulciano, and then when the rain got too bad, grabbed groceries and came back to the house. I think we were all back in our jammies by 3:00 p.m. The rest of the day was a blend of napping, reading, cards, and snacking. We went to bed early and indulged in the rainy day.

Before the week started we each decided on something that was essential for our trip. I really wanted to revisit Orvieto, Phil wanted a massage (they are prohibitively expensive here in Switzerland), and Adam wanted to taste wine in Montalcino, which is known for their world class wine. So we dedicated Thursday to all things Brunello di Montalcino.

A note on visiting tasting rooms and vineyards: We were in Italy during the harvest time, which meant that the wineries were busier than usual, but no less willing to entertain visitors. That said, it’s important to check out each winery you wish to go to so you know if they are by appointment only, or if they have set visiting hours. We had to book some appointments at least a day or two in advance so it’s helpful if you know a couple places you’d like to go. We also got ideas from locals and other tourists so be open to trying new places if you aren’t too picky. We did, however, get very lucky on Friday when we were driving around Montepulciano and stopped into three different wineries without making appointments and were able to taste at all three. When in doubt, call ahead! (this post was helpful)

We scheduled an afternoon visit to Molino di Sant’Antimo and were lucky enough to be the only guests. It’s a family-run establishment and Valeria, the winemaker pictured above, gave us a tour of each part of their operation. It’s incredible to hear how much work goes into making wine each year and how much is totally out of their control. Brunello di Montalcino is some of the highest valued and most prized wine in the world and there are a lot of rules that winemakers must adhere to in order to be classified as true Brunello DOCG. This summer was hot and dry–perfect for making wine–so we are looking forward to trying the 2015 vintage, which we won’t be able to do until 2020. The 2011 will be released in February of next year but we were able to try a glass in their tasting room, which also doubles as the family’s dining room. A true family operation! It was a fantastic visit and we look forward to trying more of their wines in the future.

Afterward we went to Poggio Antico, a large winery on the other side of Montalcino. We had had a bottle of their 2007 Brunello Riserva at La Porta in Montechiello so we were eager to see where it came from. Again, we scheduled an appointment and showed up with several other tourists. The property is immense and gorgeous. The wines were delicious—and we brought several home as souvenirs for the future—but the real treat here was the sunset.

It could have been the wine talking, but this was one of the best sunsets I’ve ever seen. We debated which is the better sunset, beach or mountain/hill, and mountain/hill might win out. Thoughts? (p.s. having to decide on the winner in this debate is firmly classified under “not a real problem”.)

I can’t speak to the actual town of Montalcino because we only showed up for dinner but based on our cursory glance I would say it’s definitely worth a stop on your trip. It looks like a lot of other towns, but that’s certainly not a bad thing. We had dinner at San Giorgio (and picked up yet more wine at their wine shop across the street), but Il Giglio also came recommended. Had we time enough I would have liked to stop in the fortress where there also happens to be a nice wine bar–ask for Jo.

I’m beginning to cringe slightly at how many times the word “wine” appears in this post, but we wholly embraced the “when in Rome” ethos on this trip. We were surrounded by world class wines and it was fun to feel a part of that world for a while. And, to be honest, we also just like wine : )

The last bits of Italy coming next week!