Women’s Creativity Retreat in Umbria, Italy

Remember when you were seven and spent entire afternoons lost in finger paints and construction paper? When “I’m not artistic” wasn’t even in your vocabulary? This week is about finding that fearless creator again—the one who existed before deadlines, school pickups, and the tyranny of matching your living room throw pillows.

Perched atop a hillside with sweeping views over the Tiber Valley, Villa Castiglione Ugolino is where medieval grandeur meets modern luxury. Think rolling hills carpeted in olive groves, vineyards stretching toward distant mountains, and an infinity pool that seems to spill into the Umbrian sky. Condé Nast Traveler called it one of the most Instagrammable houses in the world—and they weren’t exaggerating.

Want to learn more?  Join us for a live trip preview on Thursday, January 29th at 6:30ET.  RSVP HERE.

For one glorious week, we’ll play. We’ll experiment. We’ll mess up gloriously and call it art (because it is). In a restored medieval church with centuries-old frescoes overhead, you’ll paint, draw, collage, write, and talk—guided by exercises that work for women who already have an art habit as well as those of you who insist you “can’t even draw a stick figure.” Spoiler alert: you absolutely can, and you’ll surprise yourself with what else emerges when you give yourself permission to play.

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Beyond our creative sanctuary, we’ll venture into Umbria’s medieval hill towns—Tuscany’s equally gorgeous but refreshingly un-touristy sister region. We’ll meet fascinating local women (including a weaver and a chef), wander cobblestone streets that haven’t changed in centuries, and collect

Beneath the vaults of a restored medieval church with guided exercises and private workspaces to help launch and encourage your imagination, we will paint, draw, collage, write, and talk.

To further spark insights about your interior space, we will use exploration of physical places, taking day trips to introduce you to some beautiful spots and women who live in ways that we think you’ll find fascinating. With a traveler’s spirit of appreciating what is around you, we hope to spur you to a deeper appreciation of yourself.

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1. The Villa Will Spoil You Rotten
Villa Castiglione Ugolino isn’t just beautiful—it’s the kind of beautiful that makes you audibly gasp. Panoramic views? Check. Centuries-old frescoes? Check. An infinity pool where you can float while overlooking the Tiber Valley? Oh yes. The entire compound radiates that rare combination of historical gravitas and pure luxury. You’ll feel like a Renaissance patron of the arts—minus the complicated politics and unfortunate plague outbreaks.

2. No Artistic Experience Required (Seriously)
Shannon and Jen have designed exercises to strike a spark in women who maybe haven’t touched art supplies since elementary school. Through playful, low-pressure activities, you’ll experiment with different media to capture the colors, textures, and feelings of your week. Shannon, an art historian and artist herself, will also help us engage with the incredible art surrounding us throughout the region. The goal isn’t perfection—it’s permission to play again.

3. Umbria: Tuscany’s Cooler, Less Crowded Sister
All the green hillsides, medieval villages, and fantastic food of Tuscany—but without the tour buses. Umbria remains delightfully under the radar, which means you can actually enjoy a cappuccino in a piazza without fighting for elbow room. It’s Italy as it was meant to be experienced: slowly, authentically, and with plenty of space to breathe.

4. Medieval Villages That Feel Like Time Travel
Our day trips to Assisi, Spello, Gubbio, Città di Castello, and Perugia offer winding streets, cafés at every corner, breathtaking views, and the kind of history that makes you feel connected to centuries of lives lived before yours. These aren’t museum pieces—they’re living, breathing towns where locals still buy bread at the same bakeries their grandparents did.

5. The Women You’ll Meet (Including Yourself)
Between the local artisans we’ll encounter and the curious, open-minded fellow travelers you’ll share the week with, this trip becomes a gateway to both new friendships and renewed self-knowledge. There’s something about an idyllic setting and genuine creative exploration that lets conversations—and connections—go deeper.

Jen Vickers splits her time between Austin and Umbria where she and her family have spent 25 years restoring Castiglione Ugolino, a 12th century complex of houses at the base of a ruined castle. She’s traveled to widely in Europe, Asia and Central America, but her favorite explorations are of the small medieval towns of central Italy. A newly minted Italian citizen, she loves to spend time in Italy.

Shannon Faseler is a visual artist and art historian who works across media. Born in Texas, she is a graduate of the University of Texas at Austin where she received a BFA in Studio art. She also holds a MFA in painting and drawing from the School of the Art Institute of Chicago.

Upon graduating in Chicago, Shannon moved to California where she exhibited, taught, and ran the University Gallery. Currently, Shannon is in Wimberley, Texas, where she continues her studio practice in addition to teaching, exhibiting, and curating at home and abroad. Shannon also enjoys traveling and leading tours of college students and adult groups to Italy and beyond.