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Undiscovered Umbria - A Week In The Green Hills
time 9 Days / 7 Nights

Assisi area (7 nights)

Discover the underrated region of Umbria, filled with castles, farmhouses, rich landscapes and gastronomic glory! Relax in the privacy of your own VILLA or step into the Middle Ages and explore nearby cities full of culture and history!

This package includes a car rental and private villa accommodations for 7 nights.

Below we have listed our top suggestions of private tours to add on as you wish. You can decide to have every day at leisure, explore on your own, add a private guide for each suggested tour or even hire a private chauffeur driver. 

Customize the package and make it YOUR dream vacation!

Click HERE to look at our selected villas in Umbria. 

inclusionAt a Glance
  • Suggested Itinerary: Departure from US
  • Arrival in Umbria
  • Perugia & Gubbio
  • Assisi & Spello
  • Orvieto, Cooking Class & Todi
  • Spoleto & Trevi
  • Montefalco & Bevagna with Wine Tasting
  • Deruta's Ceramics & Torgiano's Wine
  • Departure to US
dates Itinerary
Click on the plus sign for full day description.

Board your overnight flight and you're off to your exciting Italy Vacation! 
*Flights are not included in the price of this package.  We are happy to arrange them for you.

Whether you arrive in Rome or Florence - welcome to Italy! Head to the car rental office to pick up your car, then check in at your private villa in Umbria region for an exciting week of exploration and relax.

After you check in, take some time to explore the beautiful grounds and take in your first view of the Umbrian countryside.

*This is just a suggested itinerary. Tours as mentioned below are not included in the basic package price.  We are happy to arrange for you or customize the package based on your own interests.

The capital of the Umbria region, Perugia is a beautiful hilltop town surrounded by valleys and mountains. It was founded by the Etruscans in the 7th century BC. The historical center is one of the largest and most interesting in Italy. From the ancient Etruscan remains to the Middle-Ages, from Renaissance to Baroque, each period produced absolute masterpieces. Every visitor leaves this region astounded by its combination of historic and natural attractions. 
Then head over to Gubbio, an ancient city dating back to the Etruscan period, famous for the discovery of the Eugubine Tablets 1444. They are a set of bronze tablets that make up the largest surviving text in ancient Umbrian. Visit the city museum to see these and other treasures of the region. Gubbio is one of the best preserved medieval towns in Italy, a walk through its alleys is like going back in time.

Tonight, you can either have dinner in town or hire a private chef that will prepare a delicious Italian meal at your villa.

Assisi is a peaceful picturesque town set on the hills of Umbria. It is the birthplace of Saint Francis, the founder of the Franciscan Religious Order and the Patron Saint of Italy. St Francis renounced all of his possessions in order to devote his life to helping the needy. Here, the splendid Basilica of St Francis is dedicated to him and is one of the emblems of Christianity located on Mount Subasio from which it overlooks the entire valley. Apart from being a strong appeal for millions of religious believers, the Basilica is a monument of great artistic value.
Spello is a small town comprised of 6000 inhabitants, here you can experience the charm of a small Italian village free from tourists.
Considered one of the most beautiful villages in Italy, due to its significant environmental, cultural and artistic heritage. Three well-preserved Roman stone arches form the entry points to the town, Porta Venere, with its towers, Porta Urbica and Porta Consolare. Once inside, the cobblestone streets meander in and out of mysterious alleyways that lead to simple, yet elegant stone houses. Evidence of the Roman period coexists beautifully with today's medieval urban style. Spello is a pleasure to those who love walking!

Orvieto is a charming little hill town in the Umbrian countryside with a rich history dating back to the Etruscan times. Set atop a mountain overlooking the Umbrian valley, it is a spectacular feast for the eyes.  Experience this beautiful town in the most authentic and comfortable way.  If you decide to hire a private guide, you’ll hear fascinating stories of ancient times from your guide as you tour the historic city center including Orvieto’s famous 13th century Gothic cathedral and St. Patrick’s well, a 175 foot deep well built by the Pope in the 17th century.
Then, learn the secrets of traditional Umbrian and Tuscan cuisine with a hands-on cooking class in Orvieto. Learn how to prepare a typical Umbrian meal using locally sourced ingredients and then enjoy your lunch with a wine tasting!

In the afternoon we suggest a visit to Todi, a town perched on a tall two-crested hill overlooking the east bank of the Tiber river commanding views in every direction. During a study in the 1990’s, Todi was used as the model sustainable city, because of its scale and its ability to reinvent itself over time.  Following this, the Italian press did a report naming Todi as the world's most livable city. Interesting fact- almost all of Todi's main medieval monuments – the Gothic Cathedral church, the Captain’s Palace, the Priors’ Palace and the People’s Palace are situated on the main square which has often been used as a movie set.

Spoleto is a nearly perfect medieval city with loads of charm in a beautiful setting. The town is full of vibrant cultural opportunities and a perfect spot to visit central Italy. Spoleto is home to two important annual events - the Two Worlds Festival (Festival dei Due Mondi), a celebration of art, music and theater; and the Spoleto Jazz Festival, which bring people from all over the world. This mingling of culture and art gives Spoleto a stimulating and invigorating atmosphere. The tiny historic center is a delight to stroll through. The medieval streets are well-kept and the town maintains its ancient atmosphere. Medieval-era shops fill up the narrow streets, still being used by artisans and boutiques.
Trevi is a small town on a hillside in the heart of the Umbria region of Italy, and is rich in history and art. Trevi was originally a province of the Papal States, however political power was actually exercised by a small number of noble families and it was these families that gave much of the artistic and cultural heritage to the town we see today. The enjoyment starts even before you enter the village - the view of Trevi running down the hillside as you approach is very beautiful and one of the highlights of a visit. The medieval center of Trevi is a network of alleys and narrow streets still surrounded in part by the original defensive walls (built in the 13th century). The raised position of the town means it also has some exceptional views across the Umbria countryside as far as Assisi and beyond.

Tour the historic medieval cities of Montefalco and Bevagna. See the Romanesque, Renaissance, and Gothic churches of Montefalco and visit the Castelbuono of Bevagna. Then, savor local Umbrian products including a selection of Sagrantino and Rosso di Montefalco wines, with wine cellar visits.

Deruta is a small hill town, long known as a center of refined maiolica ceramic production. The excellent quality of the local clay encouraged the production of Deruta pottery since the early Middle Ages. Today Deruta remains known for its excellent quality ceramics which are exported worldwide. A visit to a ceramics factory and shop, and perhaps bring home a piece to remember Deruta!
Torgiano is a tranquil place, ideal for strolling streets without the worry of crowds of tourists or vendors! The ancient part of town is still partly surrounded by medieval walls.  Torgiano owes its fame to the excellent agricultural productions that have made it one of the most appreciated capitals of olive oil and wine in Italy. The most famous and appreciated wines are Rubesco (red) and Torre di Giano (white), both dating back to a very ancient tradition. You may visit the Museo del vino (Wine museum) and Museo dell'olivo e dell'olio (Olive and oil museum).  Some other interesting sights include the 13th century Torre de Guardia, San Bartolomeo church and Oratory of St. Anthony (16th century) with frescos of the Domenico Alfani school.

Sadly, today you say Arrivederci! to the beautiful Umbria. Make sure you allow enough time to fill up the gas tank, return the car and take care of any final charges (like the GPS rental). Then make your way to the airport. Hopefully you'll have time for one more cappuccino!

We hope you enjoyed this exciting opportunity to stay at a private villa, live like a local and explore the gems of the Umbria region.