Charcuterie appetizer board Outdoor table with vineyard background in Italy

The Heart of Italy Tour - Umbria

October 11 - 18, 2025

Join us for a week in the heart of Italy!

Immersed in the green heart of Italy, silent and unassuming, stands Umbria, a land of gentle hills and valleys, mushroom truffles, wine, and olive oil.

This unexplored region is surrounded by mighty walls, vineyards, and olive trees and is full of churches, sanctuaries, monasteries, palaces, and museums. In Umbria, you’ll journey through the most beautiful villages of Italy, where history and culture mix with spirituality and a landscape that captivates the eyes and soul of those who experience it. Villages perched on green hills among flowering valleys and oak forests. Umbria is a region that surprises and allows for traveling slowly. In Umbria, you’ll be surrounded by centuries-old vines trees and sunflower fields that line the roads towards precious sanctuaries. Umbria is a region where you travel slowly, continuously up and down, on green hills and brushstrokes of yellow sunflowers that line the roads towards the picturesque villages like Assisi, Perugia, and Spello.

Journey through this still somewhat undiscovered region with us for a week and get to know it via its food, art, culture, and nature. In the greenery, you will enjoy truffle hunting in the woods and long guided walks in hamlets such as Spello, Assisi, Montefalco, and Bevagna. Taste just pressed olive oil, visit several wineries, enjoy leisurely lunches in unique spots, learn about the art of pork curing, and sample the many wines this region has to offer. When you’re not enjoying amazing experiences, you can relax at the pool of your 5* hotel or enjoy some time alone, wandering the safe streets of Perugia, where you will find medieval alleys to get lost in and breathtaking views.


  • 8 days / 7 nights in 5* accommodations in the center of Perugia
  • Private transportation for all our scheduled activities during the week
  • Daily breakfast at the hotel and all lunches during the week
  • Welcome and thank you multi-course dinners with ample wine
  • Private tours with certified guides 
  • Private visit to winery in the Sagrantino area with wine tastings and lunch on location
  • Winery visit in Montefalco with afternoon guided visit in the city known for wine and olive oil
  • Food tour of Perugia with ample tastings of local products and wines
  • Guided afternoon in Assisi with entrance to the Basilica. Also time on your own to explore.
  • Visit to agriturismo for a truffle hunt in the woods with lunch following
  • Visit to olive oil mill to taste the year’s production of new olive oil
  • Guided afternoon visit to Lake Trasimeno with entrance and tour of Palazzo della Corgna
  • Hands-on cooking class in winery with large lunch following
  • Guided visit to Spello, the city of flowers and art
  • Bi-Lingual native Italian host at your service during the entire week


  • Airfare / Flights (Folks should fly into Perugia or Rome Airport).
  • Transfer from / to airport
  • Tips / gratuities for guides, instructors and drivers
  • Travel Insurance: As of 2023, we will require everyone traveling with us to carry some form of Travel Insurance. Click here for info.

Day 1 - Welcome to Umbria!

Welcome Dinner and Meet and Greet

Umbria has been called the heart of Italy, and our home base, Perugia, can easily be named the heart of Umbria. Today, we will welcome you to Umbria at our 5* hotel in the center of Perugia. Settle in and unpack, relax tired muscles in the hotel pool, or head out for your first gelato. We will welcome you to Umbria tonight with a delicious typical dinner with abundant wine. During dinner, you’ll get to know your fellow travel companions and learn all about the week ahead.

Day 2 - Cooking Class in Agriturismo + Tour of Gubbio

Hands-On Cooking Class in Agriturismo + Tour of Gubbio

Today, you’ll have to work if you want to eat! We head a little north today to the enchanting city of Gubbio. Our first hands-on culinary experience will take place in an agriturismo. An agriturimso is a working farm which produces some of its products on location. During our class, we will be preparing several local Umbrian dishes to enjoy as a group afterwards. The location, the food, the company, the wine, it’s all a perfect combination! Weather permitting, we can enjoy our lunch outdoors.

After class, we enjoy a guided tour of the city of Gubbio. The city walls, the gray stone buildings, the cobbled streets, the charming little squares – Gubbio is one of the most beautiful and best preserved medieval cities in Italy. Its alleys offer enchanting views, where you can discover a cuddly cat, an old-school Fiat 500 still in use, some clothes hanging out, or a curious nonna looking from a window . In Umbria, you are sure to discover a place of peace and spirituality.

Day 3 - Food Tour of Perugia & Assisi

Morning Walking Food Tour of Perugia, Afternoon Guided Visit to Assisi

Today, we will meet my dear friend Susan for a one-of-a-kind food tour of Perugia. Susan has been calling Perugia home for over ten years, and over these years, she has met amazing local food purveyors that you, too, will get to meet during our foodie walk. You’ll taste, sip, and stroll along the ancient streets and learn not only about these amazing foods but also about this equally amazing city.

In the afternoon, we will walk off our morning’s tastings in one of my favorite Italian cities, Assisi. Assisi is a fascinating village that seems to live in a world of its own, separated from the clamor and chaos of other cities. Thanks to its rich history and its incredible art, Assisi is a city with a multifaceted identity. During our guided walk, you will have the opportunity to wander with your imagination from the pre-Roman era to the Middle Ages, enjoying the extraordinary beauty of places full of spirituality such as the Basilica of Santa Chiara, dedicated to the founder of the Order of the Poor Clares, and the Basilica of San Francesco, home to masterpieces such as paintings by Cimabue, Giotto, Pietro Lorenzetti and Simone Martini.

Day 4 - Visit the Bevagna & Sagrantino Area with Lunch

All About Wine! Visit Several Notable Wineries in the Sagrantino Area with Lunch on Location

Umbria is increasingly becoming famous in Italy and worldwide for its food and wine specialties. One of these is undoubtedly the wine produced among the rolling hills of this region. The most famous area for wine production in Umbria is the Sagrantino area, a red wine that is making its way worldwide thanks to its unique characteristics. The Sagrantino grape is grown mainly in Bevagna, and we will visit several wineries in the area today.

Bevagna is a perfectly preserved medieval village that has become one of Umbria’s main points of reference for traditions and medieval culture. Piazza Silvestri stands out in the center of the town as backdrops to the Romanesque churches of San Silvestro, San Michele, and the nineteenth-century Teatro Torti.

After a guided tour of this charming hamlet, we will visit several wineries in the area, enjoy lunch on their property, and taste numerous local wines.

Day 5 - Truffle Hunting and Olive Oil Mill

Visit to Agriturismo for Truffle Hunting in the Woods. Afternoon Visit to Olive Oil Mill.

We’re visiting Umbria in the fall, so visiting the woods for some truffle hunting is a must. Did you know these highly prized funghi are cultivated the most in Umbria? More so than Tuscany and even Piedmont. The truffle in Umbria is a fundamental element of good cuisine. Combined with many dishes, it is an element that enriches the typical cuisine of the area. The soils of this region are rich in truffles, and living this truffle-hunting experience in Umbria will make for a most memorable experience! Experience the thrill of truffle hunting in the company of the quarryman and other expert truffle hunters. You will discover how this precious product is harvested, thanks to the talented truffle-hunting dogs, the real protagonists of our day! A complete lunch with truffle tasting will follow for a perfect conclusion to this unforgettable experience.

After our outdoor excursion and delicious lunch, we will tour a frantoio. A frantoio is an olive oil mill, and seeing as we’re visiting in the fall, we will get to taste the olio nuovo, the new oil. And Umbria is probably the region with the best quality in Italy, having won numerous global awards recently—a tradition devoted to the oil’s quality and not the quantity of production. So, while southern Italy gets most of the attention for olive oil production, oils from Umbria are also considered some of the best in Italy and the world.

Day 6 - Factory Visit and Visit to Lake Trasimeno

Morning visit to Producer for Food Tasting and Lunch with Afternoon Guided Tour of Lake Trasimeno

We will visit a local producer in the morning and learn about local products. We will enjoy lunch on their property before heading out to another unique destination for the afternoon!

In the past, Lake Trasimeno was called “the Sea of Perugia,” today, it offers a wide choice of attractions for visitors. Lago Trasimeno is a true natural gem that provides an oasis of tranquility and scenic beauty. Its clear waters and green banks surround rolling hills, medieval villages, and nature reserves, creating a unique and fascinating environment. The fourth-largest lake in Italy is located in the heart of the Umbrian hills. Today, we will visit this lovely area, enjoy a guided tour, and visit the Palazzo della Corgna, an imposing palace built on a pre-existing building lined with beautifully undiscovered frescos.

Day 7 - Cooking Class and Tour of Spello

Morning Hands-On Cooking Class of Local Specialty Product, Plus Afternoon in Beautiful Spello.

Grab your apron, and let’s head to the kitchen! Today, you will learn all the tricks to make the delicious Assisi Schiacciata! Visit one of the oldest organic wineries in Umbria, where you can learn how to create and taste this delightful special bread. After preparing the ingredients, all strictly local and with organic flour produced by the cellar with organic wheat, and kneading the schiacciata, all you have to do is wait for the quick cooking and be able to taste your dish immediately. You’ll enjoy this special bread with typical Umbrian cheeses and salumi. There will also be a special tasting of the cellar’s organic wines and the delicious extra virgin olive oil.

Make sure your camera is charged for this afternoon’s visit! After lunch, we visit Spello, one of the most picturesque towns in Umbria. This pretty town overlooks olive groves and is characterized by charming winding alleys adorned with pots of colorful flowers hanging everywhere. In the Renaissance, its main church was decorated with frescoes by Pintoricchio, one of Italy’s most important painters of the 15th-16th century. Art lovers must see it. You’ll love your time in Spello, the city of extra virgin olive oil, flowers, and art!

Day 8 - Arrivederci Umbria

Breakfast at the Hotel Before Checking Out

It’s time to bid farewell to the heart of Italy. Enjoy breakfast at the hotel before checking out for your next destination or to return home after a most memorable week in the heart of Italy.

Price & Details

8 Days / 7 Nights

Price: $5,200 USD Per Person in Superior Room / Single Supplement is $1,300 USD.
$5,500 USD Per Person in Deluxe Room.

$1,000 USD Non-refundable deposit is required to secure your spot.

Francesca Montillo, Native Italian, Owner and Tour Leader Accompanies all Activities​​. Contact Francesca at for booking/reservation and further details.

If you would like to reserve a spot for this tour, or have any questions, please use the contact form below and we will send you the necessary booking instructions or additional information.

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