Day 4&5: Breathtaking Tuscany / Val d’Orcia
Packed out bags, threw them in the car and said ‘arrivederci’ to Assisi, Lara, her family and Hotel Ideale. Headed off to the Tuscany countryside and the Val d’Orcia region which many say is the most amazing area of central Italy! Kari and Izzy kept commenting, ‘Look over there!’.
Val d’Orcia is widely celebrated as the prettiest part of Tuscany. It boasts the quintessential Tuscan landscape of gently rolling golden hills, iconic cypress-lined country roads, and medieval hilltop villages like Pienza and Montepulciano. We are soon to visit both over the next 2 days!
The drive is uneventful but probably picked up at least 2 tickets for ‘whatever’. Will know at least 3 months following the trip, as per prior adventures in Italy. We pull into Monticchiello, looking forward to seeing Francesco and La Casa Di Adelina, our BnB for the next 2 nights. But no Francesco to greet us! He is out enjoying the sea with family, back tomorrow as per his cousin. We quickly settle in, unpack, and head out to our picnic!
July 4th, 2026 – Happy 250th Birthday America!
A few short miles from Monticchiello, we found Cugusi Silvana, a dairy farm on a gravel road where a picnic awaited us.
We were given a basket filled with placemats, bread, a bread board and knife, which we filled with olives, jams, bread, drinks, salami and an assortment of pecorino cheeses, which this area is famous for.
Then we chose from various picnic tables scattered around the property all which afforded us a view of the Tuscan valley below. We greatly enjoyed our experience; we laughed, ate, talked, ate some more.
We all agreed that taking the time to slow down was worth it. Would we recommend Cugusi Silvana? Absolutely!
After this brief respite, we journeyed a few short miles to Montepulciano for some shopping therapy, all surrounded by the unequaled beauty of the Val D’Orcia region with its golden tile-roofed villas, cypress trees, and the sunflowers waving in the sun. My idea of heaven! We shopped, with Ron taking pictures of the town and countryside. The day was complete with a dinner at Daria’s in Monticchiello.
We awake to Francesco’s superb breakfast. Homemade pastries and jellies, cappuccino, eggs cooked your way on toast. Lovely! and only at La Casa di Adelina. We await a day we have been looking forward to since the last visit – Pienza!
The 8 mile drive is filled with excitement for Jane and I for we know what awaits us. Kari and Izzy cannot stop commenting on the views of Pienza as we travel around each corner on the way up the hill. It is such a pleasure to share this treasure of a town with Kari and Izzy. Thank you Lord!
The only thing we notice that is different is the greatly expanded parking area – and it is packed. It seems our ‘little known gem of a town’ has become more popular, and we find ourselves mourning the “small-towndness” (is that a word?) from yesterday. But once inside this little ‘hill town’, it doesn’t seem crowded at all as we wander the cobblestone streets. Izzy found a very cute blue skirt / dress. It is fun watching her shop! This is what she has been waiting for.
Pienza offers you views that are also unbelievable, but are special since they are seen from the wall around the Basilica and city. We hurry to the view one of our favorite views, a special house that is nestled on the scenic hillside. This was the site of parts of the Gladiator movie. We complete our early afternoon adventure with a lunch at a restaurant that is located the end of the main city street, Trattoria di Luna. It is now around 3:30 and we head back to Monticchiello for a short nap before a greatly anticipated dinner at 8:00.
What a day so far, but little did we know, the best is yet to come! Our dinner at Deb’s Lounge in Monticchiello.
(Odd name for the best dinner yet for this time in Italy?). Doesn’t “Deb’s Lounge” sound like a cheap bar of some sort? Undaunted, and following so many 10/10 reviews, we cross the threshold at 8:00pm (prime dinner time in Italy) to a wonderland of sights and smells. We enter to a lush garden at the edge of the Val D’Orcia. Lit by soft lighting, we are escorted to our table and offered a welcome drink.
Soon we meet Osmond (like the Brother’s), a waiter extraordinaire, who guides our choices for dinner. Izzy, Kari and I choose “Plin”, a rectangular, hand crafted pasta topped with truffles from the region. Like none other. Did I mention the vanilla? Melts in our mouth.
Throughout the meal, we are offered “palate cleansers” such as a ball of bread / tomato paste and anchovy bites.
For dessert, we can’t decide so we try all four then we can’t decide the one we like best. All the time Osmond regales us with stories of the famous people he has served in his time in Tuscany. His favorite? Sandy Koufax, the left-handed pitcher from the Los Angeles Dodgers back in the day.
All good things must come to an end, and so after 10:00 we bid our new friend and Deb’s Lounge, “Arrividerci”. Michelin isn’t far off I believe.
