untold italy small group tours

Umbria in Fall Tour Overview

Vineyards stretch for miles in hues of yellow, orange and red. This is Umbria during the harvest time and it’s full of mystery and allure. Sometimes described as “the new Tuscany”, Umbria is an ancient region found between Rome and Florence that has a rustic charm of its own. The people of Umbria are proud and passionate, and ensure their local traditions and rituals endure for centuries.

Our Fall Umbria itinerary is a journey of food and wine discovery that will open your eyes to this region of verdant pastures and hill top towns. Starting in charming Orvieto, we’ll head to the heart of the region to discover its Medieval cities and enchanting towns.

Along the way we’ll visit family vineyards, some of the prettiest towns in Italy, Assisi and Perugia (the home of Italian chocolate). Our tour features gastronomic experiences including making pasta, cheese tasting, and long lunches with matching local wines, all in the company of fellow food and wine loving travelers with a passion for Italian culture.

perugia umbria

The colors of Fall are incredible in Umbria as vineyards and olive groves are harvested. The air is crisp and fresh and it’s the perfect time to enjoy the hearty local dishes of the region and their specialty cured meats and olives.

We’ll try mouthwatering porchetta, local truffles and delicious Umbrian olive oil and the local Orvieto, Sagrantino and Pecorino wine celebrated throughout Italy. So come and join us as we taste our way through hidden Umbria, bite by bite.

Upcoming Umbria in Fall Tours

book now

Umbria in Fall Tour Highlights

Delicious Umbrian food and wine • Picturesque hilltop towns • Medieval cities • Truffle hunt and cooking class • Local wine and olive oil tasting • Artisan ceramics • Chocolate experience

umbria olives
tour umbria
umbria hills in fall
umbrian ceramics
umbria tour aperitivo
sagrantino wine grapes
panini porchetta umbria

What Our Guests Say About Untold Italy Tours

Magical! Beautiful! I’m a bit of a dreamer and I just got lost there last night. Lost in this beauty.. Magnificent! I just loved it – view video

Vicki / Australia

We have been to Italy several times, but never like this. It has been a wonderful experience – view video

Pati / USA

Aside from every little surprise around every corner, I’ll remember Cosimo and the genuine excitement and pride that come out of him and his storytellingview video

Steve / USA

Umbria Fall Tour Itinerary

orvieto fall

Day One

Arrive in ORVIETO

Welcome to charming Orvieto! This beautiful hilltop town is famous for its majestic cathedral and stunning hilltop views. 

Meet your host and fellow travelers in Rome this morning before we make our way to unforgettable Orvieto. Together we head to a favorite local trattoria where we have a chance to get to know one another over a spectacular lunch. Your host Olivia will let you know what’s in-store during our week together as we enjoy local wines with tasty cured meats and local pasta.

Next, it’s time for a guided walking tour through this fascinating hill-top town. Our local guide will bring this incredible town to life, recounting stories of its Etruscan past with a stop at its magnificent cathedral of course.

After taking in the sights, enjoy some free time to wander, snap some photos or do a little shopping, before we whisk you away to our charming countryside relais.

Check-in at our hotel in the afternoon and relax into the Umbrian way of life. Once you are settled in, we meet in the evening for our first aperitivo together. Enjoy a refreshing spritz or one of Orvieto’s famed white wines alongside some snacks. Salute!

  • Hotel: Charming 4 star relais (luxury country house)
  • Meals: Lunch with wine, Welcome aperitivo
  • Activities: Guided sightseeing tour of Orvieto
umbria ceramics

Day Two


Pack your bags this morning and prepare to say arriverderci to Orvieto. We are off to another beautiful hilltop town – Todi. Here you have some free time to wander the pretty streets, take some photos, or even do some shopping. There’s a wonderful shop that sells handmade linens in the main square.

With tummies beginning to rumble, we set off in search of lunch. Our destination is a lovely organic family-run winery and olive oil grove nestled in the countryside.

We tour the groves and learn how they make extra virgin olive oil and their delicious wine using indigenous Umbrian varieties before experiencing a tasting and delicious light lunch. Enjoy local goat cheeses, and pork and wild boar salumi from the winery’s favorite artisanal producer just over the hill.

As you sip your caffè (coffee), do you ever wonder who made the cup that you’re drinking from? This afternoon, we’ll find out as we head to the home of Umbrian ceramics. Here we visit an artisan’s workshop and discover the stories and techniques needed to make their beautiful ceramics. Afterwards, you have free time to explore some of the beautiful boutiques and do some shopping of course.

Laden with precious ceramics, we head towards our four star accommodation in Montefalco – home to some of Umbria’s best wine. You have a chance to unpack, settle in and take in our home base for the next three nights.

Tonight, we meet again for a delicious traditional dinner in Montefalco. One thing is for sure- pasta and Sagrantino wine is on the menu, so bring your appetite!

  • Hotel: Beautiful 4 star hotel in Montefalco
  • Meals: Breakfast, Light lunch at winery, Dinner with matching wines
  • Activities: Ceramics visit, Winery visit with tastings, Todi town visit
umbria cheese

Day Three


This morning we enjoy a later start with some free time to explore Montefalco or visit some local enotecche for wine shopping. Save your appetites though, because we have a full day of foodie adventures awaiting.

There is nothing quite like tasting freshly churned cheese and this morning we have the opportunity to taste our way through some of the very best. Prepare for a morning of mind-blowing deliciousness as we taste perhaps the freshest cheese of our lives.

We visit to a nearby family-run dairy farm in the hills of Montefalco that make wonderful Pecorino cheeses. We learn about the production and how the taste of each cheese changes depending on the season over a degustation of soft, semi-soft and hard cheese. Relax over a light lunch with freshly house-made bread, local wine, cheeses and seasonal fruits.

After our cheesy lunch, we enjoy a drive through the countryside towards another of Umbria’s stunning hilltop towns – Bevagna. We meet our local guide who takes us on a fascinating tour through town where we have the opportunity to meet local artisans and watch them work their crafts from candles to silk. This Medieval village is truly lovely and you also have a chance to wander and enjoy the scenery.

This evening, we are off to a totally biodynamic family-run winery. They are the ‘real deal’ and have bought up surrounding land to ensure that their vines are truly organic. Tonight, they have opened up their dining room specially just for us. We sit down to enjoy a traditional dinner featuring a real specialty- goose. Enjoy our delicious three course meal over a degustation of their fantastic wines.

  • Meals: Breakfast, Light lunch at cheese farm, Dinner with matching wines
  • Activities: Cheese farm visit with tastings, Winery visit with tastings, Bevagna visit
  • Accommodation: Beautiful 4 star hotel in Montefalco
black truffle

Day Four


Today we are off to one of Italy’s prettiest villages right in the heart of Umbria. This ancient town is known as the city of oil and is also famed for its celery. We arrive for a unique experience in the forest with trained dogs and our private expert local truffle hunter in search of black truffles.

After spending some time outdoors and hopefully finding a truffle or two, you’ve surely built up an appetite. Truffle is definitely on the special menu our hosts have prepared, so you can savor these decadent fruits of the earth.

Unwind after a long lunch with some free time to stroll around this beautiful Medieval town or grab a gelato, another favourite Italian pastime. This afternoon, before heading back to the guest house, we visit another local wine maker.

Today’s winery is at a small organic family run winery just outside of Montefalco. Enjoy a taste of indigenous Umbrian wines including of course a Montefalco Sagrantino, all enjoyed against the backdrop of the stunning green hills and vineyards.

We head back to our accommodation in the evening where you have free time to relax before we meet again for our final dinner in Montefalco.

  • Meals: Breakfast, Lunch with wine, Dinner with wine
  • Activities: Truffle hunt, Trevi town visit, Bevagna town visit
  • Accommodation: Beautiful 4 star hotel in Montefalco
assisi castle

Day Five


This morning we are off to UNESCO heritage listed Assisi. But before exploring, we roll up our sleeves and learn how to cook some of the fantastic Umbrian dishes we have already enjoyed. Our cooking class is held at a local woman’s house that has been in the family for generations in the tranquil countryside.

We enjoy a glass of wine and a walk through our hosts beautiful herb garden before donning an apron to learn how to make ravioli, stringozzi, or perhaps lasagne along with some other traditional dishes. We’ll relax in the panoramic terrace afterwards taking in the views and enjoying our well deserved three course meal.

A trip to Umbria would not be complete without exploring UNESCO heritage listed Assisi. This is the birthplace of St Francis, the patron saint of Italy, and is famed for its Medieval architecture and resplendent Basilica. We meet our private guide for a walking tour through town including, of course, a visit to the St Francis Basilica comprised of two equally beautiful churches.

You’ll have some free time to wander Assisi, before we continue our drive towards the capital of Umbria, Perugia. This gorgeous hilltop city is known for its chocolate and is sure to warm your heart. We check-in at our city centre hotel and have free time to unwind, grab a gelato or stroll around the Medieval streets before meeting again for a light dinner in town.

  • Hotel: Luxury 4 star hotel in Perugia
  • Meals: Breakfast, Lunch with wine, Dinner with wine
  • Activities: Cooking class and Assisi guided tour
olives umbria

Day Six


You can never see too many hilltop towns in Umbria, so this morning we journey to ancient Gubbio. Here we meet up with our private guide to learn about the pre-Roman Umbri and Etruscan civilizations as we admire the town and its winding Medieval streets.

After a beautiful walk through town, we drive through the lush countryside towards the mountains. Prepare for a truly local experience, impossible to organize unless you know some friendly locals. Today, we have the opportunity to participate in a real olive harvest and understand the steps involved. In Umbria, olive trees hold an incredibly special significance to the people – most Umbrians have their own olive trees that truly feel like an extension of their family.

Together we learn how to put up the nets and collect the olives, before we taste their special golden green ‘new oil’ – a peppery deliciousness like nothing else. Different to wine, extra virgin olive oil is at its best young.

After a memorable local experience, we sit down to lunch overlooking the splendid Appenine mountains. Our host prepares a platter of local cheeses and cured meats to nibble on before we try his signature pasta dish. Share a toast with new friends and be sure to have a little bit of room in your suitcase for a special gift from your time in the Umbrian hills.

This afternoon, we take a drive to magical Spello. A true jewel of the region, we have the opportunity to explore the town and pop into the charming boutiques. Enjoy some free time exploring town before we meet our local guide for an aperitivo and learn more about the town, its fascinating Infiorata festival and local legends. Tonight, prepare for a buonissimo dinner at one of the best restaurants in town before we head back to the hotel in Perugia.

  • Meals: Breakfast, Lunch, Dinner with wine
  • Activities: Gubbio guided tour, olive oil harvest experience, Spello aperitivo
  • Hotel: Luxury 4 star hotel in Perugia
perugia city in fall

Day Seven


Are you a chocolate lover? You will never forget our final day in Umbria. Perugia is a city famed for its chocolate and plays host to the annual Eurochocolate Festival. It’s also famous for the Perugina company factory which makes millions of “Baci” chocolate kisses each year – each individually wrapped with a special love note.

Today we’re going to take a look at the city’s artisan chocolate making traditions that are the true chocolate heritage on which this company was built on.

We visit an artisan chocolate maker and see how they make their delicious pralines, chocolates and other sweet treats by hand each day. Together, we roll up our sleeves to learn how to make these fantastic sweets and have the opportunity to craft our own creations and take some home.

After our chocolate class, we get to know Perugia a little better with a delightful food and history walking tour. We meet our local guide who shows us around the best culinary spots in town and recounts the stories, legends and tales of Perugia. Bring your appetites – we hear porchetta is on the menu!

After a few hours of eating our way around town and discovering some of the most famous sights in the city, it’s time to say farewell to Umbria. Rejuvenated and inspired after our week long excursion in Umbria, we’ll make our way back to Rome where you can continue your Italian adventures. Ciao, for now!

  • Meals: Breakfast, Lunch included in food tour
  • Activities: Artisan chocolate experience and guided food walking tour in Perugia
  • Group departure transfers to Rome

Umbria in Fall Tour Inclusions

We have strived to make our Umbria tour as all inclusive as possible with no hidden surprises. Included in your tour are:

  • 6 nights in charming luxury 4 star accommodation
  • 4 guided walking tours with expert local guides
  • Unique experiences: Cooking class, 2 winery visits, truffle hunt, olive grove visit and tasting, gourmet walking tour in Perugia and artisan chocolate experience
  • Meals: 6 breakfasts, 6 lunches, 2 aperitivo and 4 dinners as specified in the itinerary, wine and bottled water is included with meals other than breakfast
  • Luxury air-conditioned mini-bus
  • Tips and gratuities for drivers and guides
  • Group arrival and departure transfers to and from Rome
umbria olive groves
umbria produce
umbria in fall
trevi olive trees

Umbria in Fall Tour FAQ

Accommodation on Tour

We have three wonderful boutique 4 star accommodation stays on our Umbria in Fall tour. Close to Orvieto we stay at a charming wine resort before moving to our beautiful base in Montefalco, complete with frescoes on the ceiling. We’ll be in the heart of Medieval Perugia, close to local shops and views of the countryside beyond, for our final stop.

Meet Your Host

Olivia is an Australian woman living in Rome, with a passion for the land of la dolce vita, cooking and wine. Her super powers include finding the most charming villages and delectable cheeses.

Olivia is your local host that ensures your trip is memorable for all the right reasons.

Arrivals and Departures

Our tour begins in Rome at 10am where we will collect your luggage and begin our adventures in Umbria. Our activities conclude in the afternoon of our final day back in Rome at around 5pm. Inquire if you need assistance with hotels in Rome or planning transfers.

Upcoming Tour Dates

  • 2024 – November 1- 7 – book now
  • Exclusive tours available on request for groups of 6-10 – inquire

Booking information

  • Price from $US 5,190 per person based on twin share accommodation
  • A supplement applies for solo travelers wanting a private room
  • 30% deposit required to reserve your spot
  • Cancel for a full refund up to 120 days before departure
  • Read complete terms and conditions

Discover Umbria

Hidden in plain sight to the north of Rome and south of Florence, Umbria is sometimes referred to as the “new Tuscany” but this region has plenty of charm in its own right and a proud and unique culture, largely untouched by waves of conquests and immigration that influenced other Italian regions.

Umbria Travel Guide

Uncover the highlights of the region


Dishes from Umbria

Tastes of Umbria to try on tour

listen to podcast