Creativity Retreat in an Italian Hilltop Villa

At a Glance

Umbria, Italy
May 10 - May 18, 2025
8 Nights
Level: 3
We rate all trips on a 1 to 5 scale. A designation of 1 would be trips with the least amount of activity, such as our beach trips, where it's up to you if you'd like to be active. Our adventure trips (such as the Inca trail hike) are a 5. Most of our trips are rated 3, for people who don't mind a fair bit of walking.
12-16 Travelers

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Deposit: $1,000

Home >Trip >Creativity Retreat in an Italian Hilltop Villa

Trip Description

About this trip

Exploration, Inspiration, Culture, Community

 At Villa Castiglione Ugolino, a sumptuously renovated 13th century hilltop castle in the heart of Umbria.

During a week of play and exploration, we will have fun together creating expressions of what we value and want to remember about who we are, our authentic selves.

Read our story on an earlier Creativity Retreat here. 

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.

NextTribe members get a $100 discount. Become a member here. 

Villa Castiglione Ugolino

Atop a hillside overlooking the Tiber Valley lies the stunning Villa Castiglione Ugolino. The luxury residence offers panoramic views over rolling hills, green fields, olive groves, and sprawling vineyards.

You can take in the spectacular views from the heated infinity swimming pool before relaxing in the sunshine on the surrounding sun loungers. Throughout the grounds are several outdoor lounge and seating areas, as well as an al fresco dining table overlooking the surrounding valleys.

Inside the villa, the vaulted ceilings, reclaimed terracotta floors, travertine marble staircases, and 13th-century frescoes add to the property’s opulence, blending traditional design with modern comforts.




SATURDAY, May 10th

Welcome to the Villa

We will gather at a pre-determined location in Rome for transportation to Villa Castiglione Ugolino, the lovely 13th Century compound that will be our base for the week.

After we’ve settled into our rooms, we’ll meet for an aperitivo followed by a catered dinner either in the chapel, with remnants of early frescoes still visible, or out on a patio overlooking the valley. We’ll get a wonderful introduction to the happenings over the coming week.

SUNDAY, May 11th

Creativity introduction and Gubbio

We’ll start the day with breakfast overlooking the valley then spend the morning with some playful exercises that help open up our creativity. Break midday for lunch at the iconic Taverna del Lupo in nearby Gubbio and then wander the winding cobbled streets of this medieval town. Return to the villa at Ugolino to rest up before aperitivo by the pool and dinner.

MONDAY, May 12th


We'll depart after breakfast for the historic town of Assisi, a UNESCO world heritage site and the birthplace of St. Francis, the patron saint of Italy, founder of the Franciscan order and one of the most popular Catholic saints in history. The architecture is stunning and we'll make sure to visit the Roman church, St. Francis' home and the basilica.

Lunch will be on your own, but we'll meet up to visit another breath-taking town, Spello.

Once we get back to Villa Castiglione Ugolino, we'll have free time for a swim in the infinity-edge pool or studio time. Over an aperitivo, we'll talk about the creative process and learn about the art history of the region. Dinner will be at the villa.

TUESDAY, May 13th


We’ll start the day with yoga on the villa’s lawn, for those who want to get some stretching in. After a few creative mental exercises, we’ll enjoy a light lunch at the villa, then it’s off to Perugia, capital of the region of Umbria.

The hilltop setting is spectacular, as are its fine old buildings. Before it came under Roman rule, ancient “Perusia” was one of the twelve cities of the Etruscan federation, and considerable sections of the Etruscan walls, which extended for 2,800 meters around the town, have been preserved.

We’ll meet a local weaver, who will talk about textile design. We’ll have time to explore the city streets, shops, and museums, and will end the day at a beautiful restaurant in one of the lovely plazas.


Pasta Making and Dance Party

Today we’ll be staying at the villa, but we’ll have many visitors, including a local chef who will teach us how to make pasta from scratch. We’ll actually be eating our creations for lunch.

After an afternoon spent relaxing at the villa, we'll have a light dinner, then we'll turn the chapel into a disco and dance to a local DJ.

THURSDAY, May 15th

Citta Di Castello

Today, we’ll head to one of the best markets in the region, in the charming town of Citta di Castello, where we'll have a delightful lunch in one of the town's loveliest restaurants.

Following lunch, we’ll have free time for relaxing before dinner.

FRIDAY, May 16th

Wine-Tasting and Farewell Dinner

The morning will be devoted to relaxing or creativity exercises. Then we’ll break to take a walk down the hill to Vineria di Carmine for a wine tasting and lunch. We’ll have free time in the afternoon and then we’ll have a light dinner and a farewell party.

SATURDAY, May 17th

Depart Villa Castigliano Ugolino

Alas, our week comes to an end. We’ll take a van to the town of Todi on our way to Rome. We'll stay at sweet hotel in Rome, where travelers can relax before their further travels or catch dinner together.

SUNDAY, May 18th

Leaving Out of Rome

Everyone on their own to catch flights to the U.S. or other destinations Itinerary is subject to change because in the real world, things can change. But we promise that if we have to substitute a restaurant or activity it will be of equal or better value.


Fly in and out of Rome (FCO).

In the early afternoon of Saturday, May 10th we'll meet you at a central Rome location (probably the central Termini train station) for the 2 1/2 hour drive to the Castiglione Ugolino in Umbria, which will be our home for the week.

After 7 nights at the villa, vans will take you back to a central Rome hotel, where you will stay for one night. You will make your own way to the airport on Sunday, May 18th for your flight home or to other destinations.

If you want, you can arrive in Rome early or stay later, but know that the trip begins in central Rome on May 10th and ends in central Rome on May 18th.

What's Included

  • 8 nights Accommodations

7 at Villa Castiglione Ugolino and 1 at hotel in Rome area

  • 7 Dinners

All but last night in Rome

  • 7 breakfasts

  • Wine at lunches & dinner

  • Creativity Sessions

  • Talks & Demonstrations

By local artistans

  • Pasta-Making Class

  • Yoga at villa

  • Transportation

To and from Rome to Umbria, and around Umbria.

  • Art Supplies

  • Handmade leather book

For your art/writing/collage

  • Wine Receptions

  • Local Knowledge

Locals will offer guidance on all to see and do in the vicinity

  • Friendship and Support

On your creative journey

What's Not Included

  • Airfare
  • Airport transfers
  • Alcohol not mentioned above
  • Tips

Gratuities to local guides, drivers, maids and hotel staff, 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.

Additional Add-Ons


Castiglione Ugolino

Umbria, Italy

Our travelers love us (yay!)

Colleen M., California

What I love about the NextTribe trips is that there is so much camaraderie of other women that are like you, and then the fabulous things that the organizers puts together to give you that viewpoint, it’s awesome.

Courtney M., Texas

What I love about NextTribe trips is that you get the experience from an insider’s perspective—someone that has ties to the community and focused on building relationships from the start. I’ve been on a trip with another women’s travel group that dropped a guide in, not personally knowing anything about the locale, traditions, or culture. She was there to make sure you showed up on time, got on the bus, etc. With NextTribe, you feel like you’re having a personalized experience with your best girlfriends.

Donna B., Washington

I didn't know anyone going on the trip but that didn't stop me from signing up. I have learned that some of my life's greatest adventures have come from taking a risk and jumping in feet first. So glad I did with NextTribe! I may not have known anybody at the start, but now I feel like I know everybody.

Connie B., Pennsylvania

I love to meet and interact with strong, mature women from across the country as we learn together.

Leslie M., Georgia

I always come by myself on NextTribe trips because I like to meet super fun and interesting women. We're always doing fun and interesting things in great cities that you couldn't do on your own because you wouldn't know the people or places or the insiders.

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NextTribe fills the need I have to travel with older interesting women who are curious about the world and want to share the journey.

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Frequently asked questions

What’s different about your trips?

We curate trips specifically for curious, engaged women over 45. You’re pretty well assured that your fellow travelers will be a lot like you–since you’ve all responded to the idea of “aging boldly.”. That means built-in compatibility in your small group, including the woman who is leading the adventure.. In addition to specializing in group travel for people who don’t normally like group travel, we also pride ourselves on creating experiences that allow you to interact with local women or get deeper into the culture than you would if you planned the trip yourself.

Where do you go?

We have a wide range of weekend jaunts here in the U.S. for those who want a quick getaway. We also love taking women to Mexico, where founder Jeannie Ralston used to live. We’re always talking about pushing boundaries, and we’re doing that in the geographic sense too. For those with more time, we offer trips all over Europe, to India, Vietnam, Peru (for a hike on the inca Trail to Machu Picchu). Soon, our travelers will be getting passport stamps in even more countries on six continents. Be saving those frequent flier miles!

What do you mean by transformational travel?

NextTribe is affiliated with the Transformational Travel Council, an international group of travel professionals dedicated to making the world a better place, one trip and one traveler at a time. We recognize that travelers, especially post-pandemic, are looking for more than just a date and a destination. They can shop for that anywhere online. Our community honors the intention behind a traveler’s investment in a trip. Our travelers want to have fun (we do too!) and to travel with a sense of purpose and belonging. That’s why we go to great lengths to provide ways for women to self-select by reading the articles in our magazine and the content of our website. If you like what you see, you’re likely to be a NextTribe traveler, and we look forward to seeing you on a trip soon!

What if I travel solo?

If you really prefer to book your travel yourself and go it alone, we applaud you. That’s brave and bold and we would never try to talk you out of it. But our trips are designed so that even a woman who’s used to traveling alone, or someone shy about meeting new people, will feel comfortable in our group. Our trip leaders are there to “read the room” and make sure everyone feels included and respected.

What if I don’t like group travel?

We don’t either! Not the way most groups do it. If you feel like doing what the group is doing, great! Join us for dinner or just some of the activities. All the benefits of solo travel and the comfort of being with a group. Our groups are small (normally around 12 to 14 women) and in most situations, you are free to opt out of an activity. We figure you’re grown-ass women who know what’s best for you.

What’s the price range of your trips?

We are committed to providing what we call “affordable-luxury” travel. Don’t expect
the Four Seasons, but who wants to stay in a gilded bubble anyhow? We always look for good value and offer wonderful hotels and memorable experiences that won’t break the bank and will get you closer to how locals live. Our prices depend on the length of the
trip and the destination. We offer domestic trips for under $2,000 for a shared room, which we encourage. If you don’t have a roommate we will match you with someone. Sometimes this has resulted in lasting friendships with new travel buddies., Some of
our longer trips–two weeks in India or Vietnam, for example–will cost between
$4,800 and $6,000.

What’s included in the price?

Our trips cover most everything you’ll need to dive into a destination. Hotels and most meals, plus special experiences such as hands-on classes and sessions with local artists, writers or entrepreneurs are almost always included, but each trip is different so please be sure to read The Experience and the itinerary. We occasionally have an add-on for an extra price, but those are clearly designated. What’s not covered as a rule are airfare, alcohol and tips.

Do you have payment plans?

We sure do. It’s easy to pay for our trips by setting up automatic credit card charges at regular intervals, interest free. Think of it as the layaway plan to feed your soul.

How do I get trip discounts?

Our NextTribe members get a discount on every trip. Plus, members are the first to hear about new trips and receive upgrades on rooms if they’re available. Check out our three different membership levels here.

What’s the average age of women on the trips?

We welcome all women over 45, but most of our travelers are in the 50 to 65 age range. More important than age is the spirit of the traveler–her curiosity about the world, and her eagerness to embrace new opportunities. We’ve found women of any age with those qualities fit in well with our groups.

What’s the activity level of the trips?

Most of our trips are geared for active travelers who like to walk–a rating of 3 on our 1-5 rating scale. Here are some examples of how we rate. A designation of 1 would be our beach trips, where it’s up to you if you’d like to stroll down the beach, or play in the waves or walk around the small town. Trips where we have dedicated transportation for much of the time (such as India) are a 2; Paris is a 3 because we believe the best way to appreciate a city is to view it on foot. San Miguel de Allende, Mexico, is a 4, because you’ll be walking up some hills (at 6,000 feet altitude) and occasionally on cobblestone sidewalks. Our Inca trail trip is a 5, as are our more adventurous outdoor trips.

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