A Weekend in Tuscany's Val d'Orcia Region

The Val d'Orcia region of Tuscany is a protected UNESCO World Heritage site.   Located south of Siena, it's home to some of the most gorgeous vistas in Italy.   I cannot wait to return.The first night we stayed at La Bandita.We arrived just in time to drive back down the steep hill to have lunch at Dopolavoro.  Originally built by the Origo family in 1939, it was the meeting place for the workers on the La Foce estate.  Dopo lavoro, translated to English, means after work.  During the war locals came to watch news reels. The Origo family still owns the La Foce estate and opened the restaurant (after a lengthy restoration) in 2012. Our lunch was excellent.  Annalee doesn't eat meat and found plenty of dishes to choose from (not so easy in Tuscany). The restaurant has a large vegetable garden and uses olive oil from the estate.  On a design note, it was perfection.  Great service too.  We decide to take a power walk before dinner.   I'm relieved we missed the family of boars spotted by the other guests.  I don't know why boars freak me out.  Maybe because they're wild animals and the adults are massive?  I love being out in country but not really a fan of bugs, snakes, and such.  I know this is not logical. During dinner we met an American couple and a young couple from Poland who had recently become engaged.  We had a wonderful time.  The conversation flowed and the food prepared by Chef Dario was delicious.  You never know with communal dining.  I got a little nervous once politics came up but it was fine. Most of our discussion centered around, food/wine, travel, and the places we've visited so far in Italy.It began to rain so we couldn't light the large fire pit.  Tears.  Instead we went old school and played records.  John, the co-owner of La Bandita, is a former music industry executive and has quite the eclectic collection of vinyl.  I found an Earth, Wind, and Fire LP and it was a wrap.  EW&F is one of my favorite bands.  I side-eye people who tell me they dislike them as their catalogue is pretty deep. Perhaps they do not like music, period.  Or maybe they don't like R&B or soul/funk? I met a person who told me they couldn't stand EW&F.  This person was also a black American Gen-Xer.  I was so shook, I didn't even know to say.I cracked up when Annalee started line dancing with Chef Dario and his colleague Paolo.  It was the perfect way to end a spectacular day.The next morning, I woke up at my usual time and watched the sun rise. All I could hear were sheep and roosters in the distance.  Paradise.During my run before breakfast, I was trying to figure out when I could return La Bandita.We decided to have lunch at the Countryhouse before driving to the Townhouse in Pienza as it was the nicest day of the weekend.  It was delicious, and very pretty.I've been to Pienza before but it was Annalee's first time.  I adore this small hill town.   The first time I was there was during the dead of winter.  This time around Pienza was crowded with large tour buses dropping people off.  However, once aperitivi hour arrived, it cleared out a bit.  We met Ondine (co-owner with John of La Bandita) for an aperitivo at a new place in town.  The views were just ridiculous.  Hello, is this real life?The next morning I did a quick workout before the rain arrived.  Annalee and I got completely lost, in the pouring rain, looking for Monteverdi.  It was worth it because we ended up driving through a stunning nature reserve.I was excited to finally see Monteverdi.  Ilaria Miani was the interior designer and I had interned in her showroom.  I couldn't want to see the spaces, that were floor plans during my internship, in person.American Michael L. Cioffi started buying and renovating villas in the village of Castiglioncello del Trinoro in 2003.   He and Ilaria have created a special place that respects the history, culture, and beauty of the borgo while restoring it, a difficult feat.     We ate lunch in the entoeca.  Outstanding.   The service was incredible.  As I mentioned earlier Annalee, doesn't eat meat. The chef went to the other restaurant on the property to order some fish for her. The sun was trying to make an appearance.Monteverdi is an unique experience.  There are full time residents who have lived in the borgo for decades.  However, this isn't a Disney version of a borgo.  Locals and visitors attend the concerts, art shows, and other events held in the village's 14th century church, Sant' Andrea.Unfortunately, our weekend was coming to an end and the forecast called for rain all day.  When I woke up, I saw that the sun was shinning.  I flew out of my room to take advantage of the change in weather.  If some of these vistas seem familiar it's because many films were shot on location in this area. The verdant hills of the Val di'Orcia have been inspiring artists for centuries. I highly recommend a visit.Photos: Me and my iPhone