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Umbria & Tuscany in Our Own Private Villa

May 8-15, 2027
Umbria & Tuscany in Our Own Private Villa image
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NextTribe Discovery Call: Questions about this or any other trip? Click here to schedule a phone call with Jeannie Edmunds, COO of NextTribe.

One historic villa as a home base, two of Italy's most beautiful regions, access you can't buy.

For one week, a spectacular estate above the Upper Tiber Valley is entirely ours. We're talking an 800-year-old chapel wrapped in original frescoes. Bedrooms dripping in splendor. An infinity pool that seems to spill into the Umbrian sky. Windows and porches with expansive vistas over endless olive groves and stone ruins.

Condé Nast Traveler called it one of the most Instagrammable houses in the world. And the hotel company that manages the villa was just awarded a Michelin key for hospitality.

You could technically rent this villa yourself. What you can't get on your own is what NextTribe brings to it: a 25-year friendship with the family who restored it; a co-leader who knows every medieval town nearby; another co-leader whose art historian background helps us truly see the frescoes, light and craftsmanship all around us.

On the days we venture out from this hilltop heaven, we explore both sides of the border: Umbria's medieval hilltowns of Gubbio, Assisi and Perugia, plus a day in Tuscany's Cortona, the sun-washed Etruscan town made famous by Under the Tuscan Sun. We'll meet women who've built their lives around their crafts — a glassblower, a ceramicist, a leather artisan, a century-old weaving atelier — make paint the old-fashioned way in Assisi, and roll fresh pasta with a local cook. Every outing brings back colors, textures, and stories.

At NextTribe, we believe this stage of life — 45 and beyond — is exactly the moment to say yes to more of it: more beauty, more ease, more time that belongs to no one's schedule but your own.

We have easy, interest-free payment options.

Groups stay small on purpose — this estate, and this week, are built for a group who'll actually get to know each other, not get lost in a crowd. That means this trip fills fast.

~ Small groups — women 45+ ~ Solo travelers welcome

~ A Michelin Key–honored villa most people will never see the inside of

~ Umbria and Tuscany without ever repacking your suitcase

Solo Traveler? You're in the Right Place.

You won't be the only one. A good number of the women on this trip come solo. You'll land among women in exactly the same boat, by design.

Hosts who are just like you. Shannon and Jen lead every session themselves — this isn't a drop-in art teacher, it's women who know this villa and this region intimately, and who make sure no one sits alone.

Built-in togetherness--or not. Shared meals, shared playshops, shared piazza wanders . But plenty of glorious nooks and crannies if you need your own chill time.

Rooming made simple. Travel solo with your own room for a single supplement, or let us know and we'll match you with a roommate from the group.

What Our Travelers Say

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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.

People say if you 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.

The trip to Umbria was truly magical. This trip provided an opportunity to stay in a restored 13th century villa, waking up each morning to extraordinary vistas and exploring five unique towns, each with historical significance. I feel personally enriched by the uniquely curated activities from pasta making, to soaking up the rich ambience of the Italian countryside.

--Sandy S.

All I can say is I came back from the Umbria trip a different person. I am so appreciative of my experience that NextTribe offered to me. I must say my stress level just melted off me on this trip. I could go on and on about everything from the wonderful accommodation of Castiglione Ugolino, to the shopping in the nearby towns, the fantastic winery down the hill. And so much more!

--Tammy S.

This trip was a meaningful and unforgettable experience! Communal living and cooking together spoke to my love of the sisterhood of amazing women; the culture, food and vino spoke to my heart and soul in a very deep way.

--Peggy M.


5 reasons we love this trip

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1. The Villa Will Spoil You Rotten

This isn't a hotel — it's a 12th-century complex of houses at the base of a ruined castle, restored over 25 years by a family who has been friends with NextTribe's founder for years. Panoramic views, centuries-old frescoes, an infinity pool over the Tiber Valley — the kind of place celebrities book quietly for milestone birthdays (such as when Dan Levy celebrated his 40th here). It's run by Tenuta di Murlo, freshly honored with a 2026 MICHELIN Key for exceptional hospitality. For one week, it's simply yours.

2. One Villa, Not a New Hotel Every Other Night

Most Italy trips have you living out of a suitcase, checking in and out every other day. Here, you unpack once. The estate is home base for the whole week — even our day in Tuscany is an easy round trip. That means mornings on the terrace, afternoons by the pool, walks among the olive groves, and the freedom to skip a day trip guilt-free if all you want is to laze about.

3. Umbria and Tuscany: Two Regions, One Home Base

Umbria is often called Tuscany's cooler, less crowded sister. On this trip, you get both. Our day trips take us into Umbria's medieval hilltowns — Gubbio, Assisi, Perugia — and across the border to Cortona, the Etruscan hilltown in Tuscany with sweeping views over the Val di Chiana. Cobblestone streets that haven't changed in centuries, artisans' workshops, long lunches. It's the Italy people wish they'd found before it got famous.

4. Art, Seen Through Someone Who Knows It

Shannon, our co-leader, is a working artist and art historian. As we move through these towns, she helps us actually see what we're looking at — Giotto's frescoes in Assisi, the light, the reasons this part of Italy has pulled artists here for centuries. And when we try our own hands at it, making paint the old-fashioned way in Assisi or rolling pasta at the villa, it's pure play: no assignment, no performance, just a deeper way of seeing.

5. The Women You'll Meet (Including Yourself)

With Jen Vickers' deep connections to the region, we get to meet fascinating local women you'd never encounter on your own: a glassblower in her home studio, artisans in Cortona, the weavers of Perugia's Atelier Giuditta Brozzetti, and Rosa, who'll teach us her pasta. Plus, there are the curious, unhurried travelers sharing the week with you, which means this trip becomes as much about the company as the villa. There's something about a week with no rush to it that lets conversations go further than they would anywhere else.

Questions We Hear All the Time

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Do I need to come with someone?

Not at all. Plenty of NextTribe travelers come solo, and this group bonds fast.

How much time do we spend in Tuscany?

One full day in Cortona, the Tuscan hilltown just across the border, for wandering, shopping, lunch and visits with local artisans. The rest of our outings are in Umbria, which sits right next door. You get the best of both regions while sleeping in the same gorgeous bed every night.

What is a MICHELIN Key?

It's the Michelin Guide's award for truly outstanding hotels — the hospitality world's version of a Michelin star. Tenuta di Murlo, the company that runs our villa and its estate restaurant, Il Caldaro, earned one in 2026. In other words, you're in very good hands.

How much walking is involved?

A comfortable amount — cobblestone streets in the hilltowns, an easy pace, nothing that resembles a hike. The longest stretch is our stroll down the hill to a neighboring winery. This trip is about lingering, not covering ground.

What's included?

Your stay at the villa, breakfast every day, six lunches and seven dinners, day trips to Umbria's hilltowns and Tuscany's Cortona, artisan visits, a wine tasting, paint-making and pasta-making classes, and a NextTribe host throughout. International flights are not included.

Will I know anyone?

Probably not at the start. Almost certainly by day two. That's just how this works.

I've heard about NextTribe's creativity sessions in Umbria. Are they part of this trip?

Not this time. We've traded the creativity sessions for more time out exploring, including our day in Tuscany. You'll still get your hands busy, making paint in Assisi and pasta at the villa, but there's no studio time on the schedule.

What if I need to cancel?

Full refund up to 90 days out (except for your deposit, which can be applied to a future trip). We highly recommend travel protection insurance, and can point you toward options.

Meet Your Trip Leaders

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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.

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Day 1

SATURDAY, May 8th
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Welcome to your Castle

We'll meet in Rome and travel together to Villa Castiglione Ugolino, arriving late afternoon to a glass of prosecco. After settling into your room (and probably taking seventeen photos of the view), we'll gather around the fire pit as the light softens over the valley.

Then it's a catered, family-style dinner in the villa's 800-year-old chapel, where original frescoes still grace the walls — the perfect setting to kick off the week. Consider it your official permission slip to leave your regular life behind.

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Accommodation: Castiglione Ugolino Villa

Check inSaturday, May 8, 2027
Check outSaturday, May 15, 2027

Perched on a hilltop above the Tiber valley, Villa Castiglione Ugolino draws you into a timeless embrace of history and elegance. Once an ancient 13th-century castle and church, it now unfolds as a grand sanctuary, ten beautifully appointed bedrooms and luminous living spaces where stone, wood, and light meet in gentle harmony.

Outside, an infinity pool seems to melt into the valley, while panoramic terraces, shaded pergolas, and an outdoor hot tub offer intimate corners for slow afternoons and evenings under the rising stars. At sunrise or nightfall, Villa Castiglione Ugolino becomes a retreat of serene grandeur, a place where history whispers, nature unfolds, and luxury takes its most poetic form. The villa is managed by Tenuta di Murlo, recipient of a 2026 MICHELIN Key, the Michelin Guide's recognition of the world's most exceptional hotels.

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Day 2

SUNDAY, May 9th
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Medieval Gubbio

After a leisurely breakfast, we'll head to Gubbio, one of Umbria's most perfectly preserved medieval towns, to wander its steep stone lanes. Lunch is at the iconic Taverna del Lupo.

Then we'll visit a local glassblower at her home studio to watch molten glass become art. Back at the villa, the late afternoon is yours. Dinner is a relaxed pizza night, with pies delivered from Il Caldaro, the estate restaurant of our Michelin Key–winning hosts.

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Day 3

MONDAY, May 10th
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Into Tuscany

Today we cross into Tuscany. Cortona, perched high above the Val di Chiana, is one of the oldest hilltowns in Italy, with Etruscan roots and the sun-washed charm that made Under the Tuscan Sun a classic.

We'll wander its steep streets and boutiques, then settle in for a long Tuscan lunch. In the afternoon, we'll meet local artisans, including a ceramicist and a leather craftswoman, in their workshops. We'll be back at the villa by early evening for a simple Italian supper of fresh bread, cheeses, salami, salad and wine.

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Day 4

TUESDAY, May 11th
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Villa Life and Wine Among the Vines

A day to savor home base. After breakfast, Jen opens the doors to her own house on the estate for a personal tour — with mimosas. Around midday we'll walk down the hill to Vineria di Carmine for a wine tasting and lunch among the vines.

The rest of the afternoon is yours: the pool, the hot tub, a book on the terrace. Dinner is a light, homey supper of roast chicken and stuffed vegetables.

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Day 5

WEDNESDAY, May 12th
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Assisi & the Art of Paint Making

We're off to Assisi, the UNESCO World Heritage Site and birthplace of St. Francis. We'll tour the Basilica — Giotto frescoes and all — with Shannon, who turns it into a fresco treasure hunt so you'll spot details most visitors miss.

Then it's a hands-on paint-making class and lunch with local artist A. Gallo, grinding pigments the way Renaissance painters did. Afterward, wander Assisi's streets, pop into its paint shop and boutiques, and head home for some downtime.

Tonight we dine at Il Caldaro, the estate restaurant of Tenuta di Murlo, the newly minted Michelin Key–winning team behind our villa.

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Day 6

THURSDAY, May 13th
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Perugia & Atelier Giuditta Brozzetti

An unhurried morning at the villa, followed by a casual lunch spread of charcuterie, sandwiches and salads. In the afternoon, we'll head to Perugia, the hilltop capital of Umbria, where ancient Etruscan walls still stand in impressive sections.

Our first stop is Atelier Giuditta Brozzetti, a family weaving workshop since 1921, set in a former medieval church, where centuries-old patterns are still woven by hand on antique looms.

Then you'll have time to explore Perugia's streets, shops and museums before dinner at Da Cesarino, in the heart of the old town.

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Day 7

FRIDAY, May 14th
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Pasta Making Magic

Today the experience comes to us. Rosa, a local cook, will teach us to make pasta from scratch (the kind that makes you wonder why you ever bought it in a box) — and then we'll eat our creations for lunch, naturally. The afternoon is free: hike the trails around the villa, lounge by the pool, or pack slowly.

In the evening we gather for a fully catered farewell feast in the Jeffersonian style — one table, one conversation — to share what surprised and delighted us this week. Equal parts grateful and bittersweet.

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DAY 8

SATURDAY, May 15th
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Arrivederci

All good things must end. After one last breakfast with a view, 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.

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Logistics

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Arrive in Rome on Saturday, 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 Saturday, May 15th.

We will transfer you back to Rome on the afternoon of May 15th. From here, you are free to continue your travels. Unless you're going somewhere else in Europe, you will probably need to book a hotel room in Rome on this night and we will give suggestions. You could stay in central Rome, or it you have an early flight the next day, you might want to stay at the airport FCO.

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

Legal Stuff: For complete terms of service, see below

What's included

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Inclusions

  • 7 Nights Lodging

  • 7 Dinners

  • 4 Lunches

  • 7 Breakfasts

  • Ground Transportation from Rome to the Villa

  • Ground Transportation for Day Trips

  • A NextTribe host through out the tour

  • A specially curated Enrichment Guide to help you prepare for the trip.

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.

Map of the trip locations

Map

A. Umbria

Umbria, Italy

B. Rome

Rome, Metropolitan City of Rome Capital, Italy

C. Assisi

06081 Assisi, Province of Perugia, Italy

D. Spello

06038 Spello, Province of Perugia, Italy

E. Perugia

Perugia, Province of Perugia, Italy

F. Cortona

52044 Cortona, Province of Arezzo, Italy

Pricing

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Insurance

What you need to know
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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.

On this trip, we require evacuation insurance. We are also an affiliate of Global Rescue. They offer comprehensive evacuation insurance if you feel you need more than what your standard policy will cover. This is extra coverage, in addition to your travel insurance.


About us

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NextTribe

For most of history, women past child-bearing years were basically put out to pasture. This was happening even in our mothers’ time. We call bullshit on that. We believe we are at a peak in so many ways and are devoted to helping women our age live the richest, most kick-ass lives possible.

We do that by informing, promoting and connecting women–through our magazine, through our member community and through the transformative experiences of travel.

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.

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Contact Us

For more information, please contact our travel manager at travel@nexttribe.com