Fall in Italy: Harvesting Olives, Truffles and Creativity

At a Glance

Umbria, Italy

Oct 31 - Nov 7, 2025

7 Nights

12-15 Travelers

Starting At

$4,999

Deposit: $500

Home >Trip >Fall in Italy: Harvesting Olives, Truffles and Creativity

Trip Description

Exploration, Inspiration, Culture, Community

We’re thrilled to have another reason, and another season to bring a small group of women back to Umbria. Our travelers love making Villa Castiglione Ugolino, a beautifully renovated 12th century hilltop villa, their home base for our annual creativity retreats in the Spring . This year we’ve added a trip in the Fall with a different focus: the olive harvest, oil production and truffle hunting, and a few different medieval villages in the area that we didn’t get a chance to see in the Spring…Plus an opportunity to metabolize your experiences in watercolor with one of our trip leaders, an artist and art instructor, if you choose to do so. You can also just soak up the scenery and relax.

*Read our story on an earlier Creativity Retreat here.*

Want to learn more? Join our live information session on Tuesday March 11th at 6:30 ET. RSVP here. All attendees will be entered into a drawing to win $400 off the cost of the trip!

Why visit in the Fall? Here’s what NextTriber Jen Vickers–one of our guides and the villa’s owner says: “Finally, after a few years of missing it, I got back to Umbria for the olive harvest in early November. I was hit with full force by what a magical time of year it is and rediscovered that my happy place is found amidst the gnarled branches and silvery green leaves of olive trees during the raccolta. Castiglione Ugolino sits on a hilltop overlooking the Tiber River, so in the Fall we often wake up above the clouds in a sort of hush, sipping cappuccino while watching the mist lift to slowly reveal our valley below. It’s the time I most think of this place being ‘the green, golden land,’ when late roses bloom, oak leaves pop amber and red, and the sun casts long shadows.”

*Want more Italy? Book this with the Fall Adventure in Florence and Tuscany (Nov. 11-18) for a deep dive into the culture. Here’s all the info about the Florence trip.*

“The weather,” Jen continues, “is usually still perfect for lunches outside under our pergola while cool enough for long hikes in the woods or to comfortably explore nearby hill towns that are active with locals rather than packed with tourists. Towns like Città di Castello, Gubbio, and Montone host Fall festivals where you smell the wood from fires roasting chestnuts, and you can taste seasonal truffles, foraged mushrooms, fresh-pressed olio nuovo, or wild boar sauces from the fall hunts. Days are shorter yet seem to be filled with productive energy, and nights are chilly, more cozy for lingering dinners by the fire with friends or simply reading a good book to end your day. So, basically–heaven.”

*NOTE: NextTribe members get a $100 discount. Become a member here.*

5 Reasons We Love This Trip

The Villa. The history, the beautifully realized renovation, the centuries-old frescoes. It’s all here in a compound that Conde Nast Traveler nominated as one of the most Instagramable houses in the world.
The Artistic Inspiration. Even if you’ve never painted before, Shannon and Jen will inspire you to play around with watercolors, so you can capture the reds and golds of autumn in Italy and the myriad impressions you see and feel during the week. Plus, Shannon, an art historian and artist, will help us engage with the art all around us in this region.
Olive Harvesting and Truffle Hunting. At this time of year across Italy, farmers take part in the raccolta, or olive harvest. We’ll get to help in the villa owner’s own olive grove, and we’ll have the chance to experience another culinary adventure–truffle hunting in the surrounding hillsides.
Exploring Medieval Villages. We’ll take day trips to introduce you to some charming Italian towns–some will have harvest festivals and one hosts an internationally known antiques market. With a traveler’s spirit of appreciating what is around you, we hope to reignite your sense of wonder and reaffirm your curiosity about the world.
Meeting Fascinating Women–both locals and fellow travelers. Because you’re engaged with curious, open-minded women in an idyllic setting, this trip be a gateway for expanding your mind and your friendships.

Meet Your Guides: 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 (right) is an artist and art educator, with a BFA from the University of Texas and an MFA from the School of the Art Institute of Chicago. For Shannon, local art, good conversations, and great food are as important as any “must-sees” on an itinerary. She is an experienced trip leader throughout Italy and beyond.

The trip to Umbria was truly magical. This trip provided an opportunity to stay in a restored 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. I also enjoyed getting to know 15 strangers that became part of my sisterhood.

- Sandy Stern

Photos

The stupendous Castiglione Ugolino--our base for the week.

On a truffle hunt in the hillsides around the villa.

Pasta Making class

Rosa, our pasta guru, toasting us at the lunch we made under her guidance.

Creativity sessions in the villa's chapel

A bedroom in the villa

The chapel in the villa.

The living room, with a fireplace we'll certainly be using.

The villa kitchen, where we'll have our pasta making class.

Medieval frescoes are visible through out the villa.

The view from the villa.

Seen in one of the nearby towns.

Oil pressing.

The batch of olive oil belonging to Castiglione Ugolino.

Truffle pasta. Yum.

Truffle hunting dog. So adorable.

Map

Sample Itinerary

FRIDAY, Oct. 31st

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.

SATURDAY, Nov. 1st

Creativity Introduction and Olive Harvest

We’ll start the day (as everyday) with a continental breakfast overlooking the valley then, with Shannon's guidance, get started with our water color kits and brushes

Then we'll head out to the villa's olive grove to help with the harvest. You can gather as much or as little as you'd like. If you get tired you can sit and soak in the sights and sounds and maybe journal or sketch.

After a homemade lunch under a pergola with a view, we'll head to the oil processing mill in the region. We'll get to join the other farmers bringing in their haul, and see the olives sorted and sample the divine new oil produced.

Later that afternoon, you'll have time to play with your paints or journal, sketch or just relax.

SUNDAY, Nov. 2nd

Arezzo

We'll depart after breakfast for the historic town of Arezzo, known for its handsome main square used in the Oscar winning film “Life is Beautiful” and for the oldest antiques market in Italy. Once a month, more than 500 antique vendors sell their wares in the extraordinary settings of piazza San Francesco, Piazza Grande and the Logge Vasari, the very heart of Arezzo. If you're not a shopper, this is a good time for sketching, journaling, or plein air work.

Lunch will be on your own.

Once we get back to Villa Castiglione Ugolino, we'll have free time or art time. Over an aperitivo, we'll talk about the creative process and learn about the art history of the region. Dinner at the villa.

MONDAY, Nov. 3rd

Pasta Making and Relaxing at the Villa

We’ll start the day with yoga on the villa’s lawn, for those who want to get some stretching in. The main part of the day will be spent learning from a lovely local woman named Rosa how to make a fresh pasta meal from scratch. Then, we'll enjoy our pastas for lunch.

Free time in the afternoon.

TUESDAY, Nov. 4th

Exploring Medieval Villages

Umbria is filled with picturesque towns off the tourist radar. Today, we'll visit two of them: Bevagna and Montefalco.

In Bevagna , we'll see artisans who produce lovely products (stained glass, beeswax, paper, apothecary) the same way it's been done for centuries. We'll have lunch in Montefalco, one of several hilltop towns that sit like terra cotta crowns across the region. Montefalco is at the center of the wine-producing region, so this is a good chance to sample and maybe send some back home.

WEDNESDAY, Nov. 5th

Into Tuscany

After a leisurely morning and an early lunch, we’ll venture over the regional border to the town of Cortona, featured in the movie "Under the Tuscan Sun." This is a dream of an Italian village--with plenty of history and art.

We'll explore the small cobblestone streets, museums and art galleries. Then we'll visit the Le Celle Monastary. Spectacularly set on a wooded mountainside, next to a gentle waterfall, the monastery feels very much part of the surrounding nature. Ideal time for sketching, journaling or simply embracing the bucolic scene.

Dinner will be at one of Cortona's delish restaurants.

THURSDAY, Nov. 6th

Truffle Hunting, Wine-Tasting and Farewell Dinner

After breakfast, we'll head down the hill to a local winery for a scenic truffle hunt. We'll walk with the guide and his dog through the hillsides and watch the hound's nose at work. Afterward, we'll sit for a truffle-centered lunch at the winery, complete with tastings of their delicious wines.

We’ll have free time in the afternoon for more painting or journaling. Over an apertivo, anyone who wants to show or discuss projects from the week will have the chance to do so. Then we’ll finish with a catered farewell dinner in the villa.

FRIDAY, Nov. 7th

All Good Things Must End

Alas, our week comes to an end. We’ll take a van to the town of Todi on our way to Rome, where travelers can depart for home or further destinations.

Logistics

Fly in and out of Rome (FCO).

In the early afternoon of Friday, Oct. 31st 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. From there, you can follow your own plans--either to the airport for the flight home or other destinations.

If you want, you can arrive in Rome early or stay later, but know that the trip begins in central Rome on Oct. 31st and ends in central Rome on Nov. 7th.

What's Included

7 nights Accommodations

At Villa Castiglione Ugolino

All meals

Except a couple of lunches when you're out exploring on your own.

Wine at lunches & dinner

Creativity Sessions

Olive Harvesting and Pressing

Truffle Hunting in Countryside

Pasta-Making Class

Wine Tasting Lunch at local vineyard

Transportation

To and from Rome to Umbria, and around Umbria.

Art Supplies

Handmade book

For sketching, painting and journaling.

Wine Receptions

Local Knowledge

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

Credit card processing fees + a payment plan

NO HIDDEN CHARGES! Plus a payment plan that doesn't charge interest.

Friendship and Support

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

Hotels

Castiglione Ugolino

Umbria, Italy

Our travelers love us (yay!)

Colleen M., California

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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.

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Courtney M., Texas

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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.

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Donna B., Washington

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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.

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Connie B., Pennsylvania

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

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Leslie M., Georgia

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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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Teresa S., Kentucky

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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.

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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.