Dear NextTriber,

Thirty years ago, I remember Jen vickers and her husband Lee (whom I knew in Austin) talking about the property they’d bought in Umbria. They said it was sort of like a castle on a hilltop, mostly in ruins. Their plan was to fix it up and live there part of the year. I knew they’d do a great job—they had excellent taste—and they were advised by the same architect my then-husband and I had used to renovate our home in Blanco, Texas.

It wasn’t until 2022 that I finally got to see how glorious their renovation had been. When I first set eyes on their villa Castiglione Ugolino (castglione is “castle” or “walled village” in Italian), I was truly awed. The dramatic views over the Upper Tiber River Valley. The 13th century frescoes, preserved throughout the structures. The olive groves and lavenders bushes all around the property.

Starting with our first NextTribe trip in 2023, Castiglione Ugolino has left a number of travelers breathless. Since then, it’s gone on to host celebrities (appearing as the backdrop for social media posts), to earn a distinction from Condé Nast Traveler as one of the “most Instagrammable villas in the world and to be recognized by Michelin for the property manager’s hospitality.

But it’s more than the villa that makes this trip so delectable. The experience is often named by travelers as the favorite of all our adventures. I believe that’s also because of the serenity and ease of the trip (we don’t change locations), plus our excursions to nearby medieval towns that we don’t just pass through and the women we meet along the way.

Interested? Learn more about the trip and potentially win a $500 discount at our Trip Preview Zoom call—this Thursday, Oct. 22nd at 6:30 ET. RSVP here.

Jen Vickers (second from left above) has lived in the area for 30 plus years, speaks the language, knows the people and the must-see spots. Jen is one of the guides on the trip and shares her knowledge and passion with every traveler.

The other guide, Shanon Faseler (center, above), has been leading this trip for several years and as an artist and art historian, she contributes another important element. She can talk about the art we see in the churches and galleries, the story behind the creators, the architecture of the glorious buildings. This gives us a fuller picture, a better appreciation for this gorgeous part of the world.

One of the many joys of this trip: you unpack once, pour a glass of prosecco, and look out over a valley of olive groves that hasn’t changed in centuries. For one week, the view is yours. And so is the castle.

Villa Castiglione Ugolino is a restored 13th-century castle complex and your bedroom in the castle awaits! Some rooms are near the 800-year-old chapel, and all of us will enjoy an infinity pool that seems to pour into the sky.

Forget the trip where you change hotels every other night and race between crowded piazzas. Here, you settle in, slow down, and let Italy come to you.

Umbria is often called Tuscany’s cooler, less crowded sister. It’s the Italy people wish they’d found before it got famous. And on this trip, you get both: Umbria’s medieval hill towns plus a day across the border in Tuscany’s Cortona.

🏰 The villa — Mornings on the terrace, afternoons by the pool, family-style dinners in a frescoed chapel. You may not want to leave the property, and that’s allowed.

🎨 Assisi with an art historian — Shannon leads a fresco treasure hunt through the Basilica, then we grind pigments the way Renaissance painters did.

👩‍🎨 Women who make things — A glassblower in her home studio, a ceramicist and leather artisan in Cortona and a weaving atelier in Perugia that has worked its antique looms since 1921.

🍝 Pasta with Rosa — A local cook teaches us to make it from scratch. Then we eat it, naturally.

🍷 Wine among the vines — A stroll down the hill to a neighboring winery for a tasting and lunch.

Small group, women 45+, solo travelers very welcome. Days out are balanced with plenty of time to do nothing at all, and there’s no repacking all week. That’s amore!!

$5,999 for doubles

$6,999 for singles

$500

DEPOSIT

+

4 PAYMENTS (Interest Free)

Starting November 8

If you’ve followed us for a while you know how fast many of our trips sell out. One day you’re thinking about it and the next time you look it’s gone. So if you’re interested, don’t hesitate! Save your spot for $500! At the very least, come to our Trip Preview on Thursday evening.

Jeannie Ralston, Co-founder and CEO