A few days in Southern Tuscany - Part I
How we spent our time in the beautiful Val d'Orcia valley
A good friend’s wedding in Pienza earlier this June was the perfect excuse to spend a week exploring Tuscany.
We spent our time in the picturesque Val d’Orcia region in Southern Tuscany, which includes the towns of Pienza, Montepucliano and Montalcino and borders Umbria. Considered the most beautiful valley, the landscape is exactly how you would picture it, a seemingly endless expanse of rolling hills quilted in various hues of tan and green, rows of olive oil fields and vineyards, and winding ribbons of cypress and plane trees dramatically leading up to various medieval castles and farmhouses.
I absolutely loved our time here and found it to be much easier to escape the saturated tourist spots and overhyped food traps, versus Lake Como, which is beautiful, but felt overrun by Americans when we were there last summer.
I’ve divided our trip into two separate posts, this one will cover our time in Pienza and the following will be dedicated to our stay in Siena.


Pienza
Where we stayed
We flew into Rome and drove two and a half hours to the incredible Casa Newton.
I typically build trips around hotels that I want to visit. I keep a running list bookmarked in my google maps and when I think about planning a trip, I always use it as a starting point. I was thrilled to see Casa Newton, which I had saved after seeing it featured in Financial Times HTSI, was a mere 15 minutes away from downtown Pienza
Casa Newton is a design-focused boutique hotel set in a villa dating back to 1846 that actually belonged to a distant relative of Issac Newton. The expansive property, which includes nine suites in the main house, two garden guest suites, two restaurants and a vineyard, was purchased 15 years ago and meticulously renovated by Swiss architect and designer, Antonie Bertherat Kioes and her husband Philippe.
Wandering around the estate feels a bit like renting your own villa. The sprawling property includes lush gardens and a tiled pool with a cooler of Casa Newton’s private label rosé and pet nat for you to take as you wish.

While you have the character and charm of the pre-existing 1800s structure, all of the design elements feel intentional and fresh - be it the gorgeous Dedar fabric wall coverings or made to order morning breakfast served on playful Nicola Fasano splatterware. We were able to take advantage of yoga taught on a wooden platform overlooking the vineyards and morning tennis lessons on the hotel’s nearby courts.
Where we ate
The first night, we ate dinner at the Michelin starred Osmosi, located about 20 mins away at a vineyard in Montepulciano. The restaurant design was clean and modern, despite being situated in an old building, with floor to ceiling glass windows and an open veranda overlooking the countryside. The menu, which skews towards more creative fare, is pretty open ended and allows you to choose from several tasting options or go fully a la carte. We went the a la carte route and focused on the incredible seasonal pastas offerings.



The following day we drove a little over an hour to lunch at the more casual restaurant Ristorante Alle Scuderie, on the Reschio property in Umbria. The food at the restaurant was quite average but the Reschio property itself was stunning. I found the general views and countryside of Val d’Orcia to be more striking than those of Umbria, however the decor and expansiveness of the Reschio property is pretty spectacular. They offered to give us a formal tour of the property after lunch but unfortunately we didn’t have time to see it.
We drove from lunch to the small town of Solomeo, otherwise known as the “hamlet of cashmere and harmony” and home to the Brunello Cucinelli brand and factory store, which offers the current collection for ~30% off of retail prices in addition to what you receive back in VAT (don’t forget to bring your passport for the store to verify and process your VAT refund paperwork on site).

The next day we had a beautiful lunch about 45 mins from Casa Newton at Il Faconiere, a hotel and Michelin star restaurant situated on a quaint little farm estate.



The remainder of our time in Pienza was spent at wedding events celebrating our friends. They held their ceremony and reception at the beautiful Borgo Sant'Ambrogio property.


Photos from the wedding. Left: “Tuscan Cocktail Attire” wearing this Linen Dress with the Savette Symmetry Pouch in bone and these silver shell earrings. Right: The gorgeous ceremony at Borgo Sant’Ambrogio.
I will go ahead and wrap Part I of this Tuscan itinerary up. Please look out for Part II which will include a review of our stay at Rosewood Castiglion del Bosco. I would love to make this substack as interactive as possible… feel free to leave questions or comments below if you have travelled to this region or plan on it.
Thanks for reading along!
Lily
Beautifully written review of a gorgeous property! Thank you!