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.
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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 hilltowns—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 impressions, colors, and stories to bring back to your private studio space.
This isn't about creating museum-worthy masterpieces. It's about rediscovering the joy of making things just because. It's about reconnecting with a part of yourself that may have gotten buried under years of being efficient, responsible, and practical. You've spent years being productive. Join us for a week of being creative instead.
Please note that this is a sample itinerary. Accommodations and activities may change but we will always replace them with something of equal or better value.
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.
Meet Your Trip Leaders: Jen Vickers and Shannon Faseler
Jen Vickers (left) 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.
We'll gather at a pre-determined location in Rome and transfer together to Villa Castiglione Ugolino. After settling into your room (and probably taking seventeen photos of the view), we'll meet for aperitivo followed by a catered dinner—either in the chapel, where original frescoes still grace the walls, or on the patio overlooking the valley as the sun sets. Consider it your official permission slip to leave your regular life behind for a week.
After breakfast, we'll ease into creative exercises designed to bypass your inner critic and wake up your imagination. Think less "art class" and more "recess for adults."
Midday, we'll break for lunch at the iconic Taverna del Lupo in nearby Gubbio, then wander the winding cobbled streets of this perfectly preserved medieval town. Back at the villa, you'll have time to rest before aperitivo by the pool and dinner. Yes, this is your life now.
After breakfast, we'll depart for Assisi, the UNESCO World Heritage Site and birthplace of St. Francis. The Basilica alone is worth the trip—Giotto frescoes and all—but the entire town is an architectural marvel. We'll visit the Roman church, St. Francis's home, and give you time to explore on your own for lunch.
Then we're off to Spello, another breathtaking hilltop town that feels like someone's beautiful secret. Back at the villa, you can spend time in the studio. Over aperitivo, we'll discuss the creative process and the art history of the region before dinner.
Optional yoga on the villa's lawn starts the day (because stretching under the Umbrian sky is rather magnificent). After some creative mental exercises and light lunch at the villa, we'll head to Perugia, the hilltop capital of Umbria.
The setting is spectacular, and the ancient Etruscan walls that once encircled the entire town still stand in impressive sections. We'll meet a local weaver who'll share her craft and thoughts on textile design. You'll have time to explore the city's streets, shops, and museums before we gather for dinner at a beautiful restaurant in one of the lovely plazas.
Today we're staying put—but we're bringing the experience to us. A local chef will teach us how to make pasta from scratch (the kind that makes you wonder why you ever bought it in a box). Then we'll eat our delicious creations for lunch, naturally.
The afternoon is yours: hike the trails around the villa, lounge by the pool, or retreat to your studio space. This is your time to do exactly what calls to you.
We'll head to one of the region's best markets in the charming town of Città di Castello—perfect for wandering, people-watching, and maybe finding a treasure or two. Lunch will be at one of the town's loveliest restaurants.
The afternoon is free for relaxing, creating, or simply being before dinner.
The morning is yours for creative work or pure relaxation. Then we'll walk down the hill to Vineria di Carmine for wine tasting and lunch among the vines.
Later, we'll gather to share our creative breakthroughs from the week—what surprised us, what delighted us, what we're taking home. We'll celebrate with a farewell dinner that's equal parts grateful and bittersweet.
All good things must end. We'll transfer back to Rome, where you can catch your flight, hop on a train to your next adventure, or spend an extra night in the Eternal City (not included) before heading home.
Arrive in Rome on Friday, May 8th
We will meet at a predetermined location in Rome for transport to the villa around 2:00 PM. If you arrive early in Rome or from another location, you will need to make your own arrangements before the official beginning of the trip.
The trip ends in Rome on Friday, May 15th.
We will transfer you back to Rome on the afternoon of May 15th. From here, you are free to continue your travels. You will probably need to book a hotel room in Rome on this night and we will give suggestions.
We require all international travelers to purchase travel insurance. We strongly recommend trip protection insurance to protect your investment. (Scroll down for more details about insurance)
No visa is required for US Citizens to visit Italy. Please make sure your passport is valid for at least 6 months beyond the end of the trip.
You will be receiving periodic communications from us leading up to departure with other important details included. If you have any questions, you can contact our travel manager, Marcy, at travel@nexttribe.com
Inclusions
7 Nights Lodging
7 Dinners
4 Lunches
7 Breakfasts
Ground Transportation from Rome to the Villa
Ground Transportation for Day Trips
Art Supplies
Exclusions
Roundtrip Airfare
Alcohol not mentioned in itinerary
Travel Insurance
Gratuities
Gratuities to local guides, drivers, maids and hotel staff, alcohol, unless mentioned in itinerary, travel insurance, round trip airfare, passport and visa fees, personal items such as phone calls, laundry, baggage fees and items not expressly listed as included.
People say ify ou go to one European country, make it Italy. I'd add, make it a NextTribe trip! Honestly, I thought the Portugal trip was unbeatable. I am more than pleasantly surprised at the high quality of trips NT offers. NextTribe consistently delivers excellence.
Ann W.
A week spent in the most beautiful villa, with interesting woman, learning about art, local cooking/food and traveling to small villages and towns was such a delight. It was a unique and wonderful Italian experience!
Michele R.
Next Tribe requires all international travelers to purchase travel insurance.
Travel insurance can be a helpful and valuable resource to pack! It can protect the investment of your trip and you while traveling.
We partner with Wanderwell, a Certified B Corporation travel insurance provider that makes it as simple as possible by not overwhelming you with options.
They offer just a few modern, benefit-packed trip protection plans that can cover the most common travel perils related to trip cancellation, trip interruption, trip delay, travel Medical Expenses, baggage & personal effects, Emergency Medical Evacuation, and more.
Click Here to create quotes and purchase a plan through Wanderwell from our partner page.
If you prefer to talk to someone, please email support@gowanderwell.com. They will set up a phone call with you and can answer your questions.
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So many travel choices…so little time. You could spend days and days trying to put together just the right combination of destination, activities, and price.
Or you could stop shopping and start traveling with us for something that feels like the greatest girlfriend trip ever–even if you come solo. We specialize in experiences that deeply connect you to other women–travelers and locals–and create life-lasting memories. Experiences you can’t get on your own. And do it all with flexible payment options.
This video will tell you if you’re a good fit for a NextTribe trip. We are proud that we’ve become known for how quickly and deeply our groups of women bond on our trips. One of our rules: No divas, please.
For more information, please contact our travel manager at travel@nexttribe.com