A Sketchbook Journey in Tuscany with Artist Amy Wynne
Our Second Italy Retreat: September 22-29, 2025
What happens when you gather 12 artists and a soulful teacher, placing them in a setting straight out of the 11th century- surrounded by olive trees, cork forests and sweeping vistas?
In our Italy Art Retreat, something remarkable unfolded.
We arrived at our home for the week in Southern Tuscany and were immediately captivated -by Emy, the owner of Pieve di Caminino and by the family museum in the main building that pays tribute to generations of artists. When we weren’t roaming the grounds, we gathered in this beautiful space for meals, laughter, and conversation.
Each morning began with breakfast and coffee made by our (ancient and sometimes unwilling) Italian coffee makers in our individual apartments before gathering with Amy. Short lessons were held each day in the olive grove, cork forest, by the outdoor pool, or on the steps of an ancient building. Amy guided us through composition, color, perspective, and a group favorite- clouds. But Amy’s real gift is not just technique; its teaching attention. Look closer. Slow down. What do you see? Really see? This is one of the reasons we invite her year after year to lead our art retreats in New Hampshire!
All week, sketching was intertwined with explorations of medieval hilltop villages. Because Amy has spent years in this area of Tuscany, she knew the perfect, untouched Italian villages to visit. In Roccatederighi , the village is built around and into spectacular rock formations, with arches carved directly into the stone. We wandered the narrow streets to the pinnacle, where we were rewarded with panoramic views and a dramatic sunset. I think we might have seen just one person out on the street, and in the local osteria we didn’t hear a word of English -it was truly transporting!
Massa Marittima was another gem. We sketched from the steps of the Duomo, and squeezed in a little shopping before our private dinner at a wine shop. We received the royal treatment at https://morisfarms.it, a winery owned by Emy’s family. Our four-course wine tasting dinner in a private room surrounded by antiques was a once in a lifetime experience. The winery overlooks miles of farmland, providing tons of inspiration for sketching, and the golden light of sunset made it even more magical.
One of the most surprising towns we toured was Castiglioni della Pescaia. Who thinks of a seaside town when they picture Tuscany? The modern town grew around a 10th-century fortress that provides breathtaking panoramic views of the coastline, the sea, and the surrounding Maremma area. My personal favorite was the discovery of a coffee and gelato combination called affogato which translates to "drowned" and is made by pouring a hot shot of espresso over a scoop of cold gelato! Whoa- this!
Our concession to a touristy experience was a day trip to Siena. How could we not go to Siena? But I’ll admit it felt a bit like culture shock to me after our first retreat in the undiscovered LeMarche region, and the quiet beauty of Pieve Di Caminino. The town was more crowded than usual since it was market day, and sadly the La Lizza market was a shopping letdown since the traditional, local wares were hard to find. Thankfully, you scan’t beat the energy of Piazza del Campo, the astounding beauty of the Duomo and the cobbled streets that open up to gorgeous views and window boxes full of flowers spilling down! At lunch we decided the tortilla all menta in salsa di gorgonzola at Osteria Cice was the best pasta we’d had so far- and we had eaten a lot of pasta!
This week was truly a villeggiatura-a slow, restorative escape, soaking in the beauty of Tuscany and recharging our creative energy. Without phone screens or the distractions of daily life we became fully present. These 11 women arrived as strangers, and through Italy and art we created a shared space for conversation, creativity, and laughter.
The rich rewards from this retreat- and our earlier September retreat-are continuing! The 13 women in our Italy Le Marche retreat are all gathering in Williamsburg, VA in December for more laughter and love! And our art retreat women are continuing to share art and conversations in bi-weekly Zoom gatherings with Amy!
If you’d like an experience like this, get in touch! Our Italy retreat in 2026 has just one spot left, and I am honored that almost everyone is a For the Soul Retreat alum-four returning to Italy again! Several are bringing friends and sisters, so it promises to be fabulous!
We have another Italy retreat planned for the Le Marche region in 2027, and we hope to add another art retreat with Amy as well- maybe a quick “pop up” in New Hampshire this June, or Italy in 2027. And for those of you that are retreat alums, keep an eye out for a holiday party invite in Richmond! I don’t expect anyone to hop on a plane to come to a party, but there was no way I was leaving you out! Stay tuned!
Hosting these retreats and building lifelong friendships with women I otherwise would have never met has become one of the greatest joys of my life!
Thank you all!
Ciao!