Italian Exclusive Vacations

The Medieval Villages of Tuscany & Umbria

It seems that every inch of land in these regions has been filled with a small gem of architecture and art. Some of these villages are quintessential cultural reference points. No one can say to know Italy without having visited Anghiari, Montone, Arezzo, Assisi, Gubbio, Spello, Citta’ di Castello just to mention some of them. Here, time stands still. It is touching to see how these places are part of a long history of architecture and civilization. Very often there are Roman or even Etruscan ruins wisely integrated into the Medieval villages. Surely everyone who finishes a stay in Tuscany and Umbria feels a pinch of regret overlaid with a feeling of peace. Leaving Umbria means leaving the regions where, almost 800 years ago, Saint Francis felt his hearth fill with joy in awe of all the beauty that God had given to Earth. Assisi’s Saint was absolutely right.

Daily program

Day 1 / Departure from the USA
Departure from Boston.
Day 2 / Anghiari
Arrival at Rome, connecting flight to Florence. Upon arrival, transfer, by private car and driver, to Anghiari. Check in at the Hotel La Meridiana. Anghiari is a lovely and peaceful medieval village with beautiful views over the countryside. It is located in the geographical heart of the Italian Renaissance. Its surrounding wall remains almost intact, just as it was when built between the 12th and 13th centuries. The historical center is full of workshops which are the symbol and passion of the village: Ceramics and textile.
Day 3 / Anghiari
After breakfast, join your local guide for a guided tour of Anghiari.
In the afternoon, visit the Busatti textile factory. Late afternoon, transfer to Castello dei Sorci, demonstration of ancient crafts.
Day 4 / Citta di Castello and Montone
Departure to Citta’ di Castello, where “Art is in the Air”. Crossroads of great artistic and cultural ferment, the village has been enriched in its evolution of works of art from all eras, from the Middle Ages to the Renaissance. Guided visit of the village. In the afternoon, transfer to Montone, a charming town that still preserves the original medieval atmosphere. In a medieval context and surrounded by imposing walls, the town developed on two hills upon which in the north rises the Franciscan convent and in the south the Braccio Fortress. The three neighborhoods that make up the town are accessed by the doors of Monte, Verziere and Borgo Vecchio.
Day 5 / Arezzo and Cortona
Excursion to Arezzo, a town with plenty of monuments, churches and museums that offer visitors a chance to step back into history.
Guided visit to The Church of San Francesco hosting the incredible Early Renaissance fresco cycle by Piero della Francesca depicting the Legend of the True Cross and to the Church of San Domenico with the wooden Crucifix by Cimabue
In the afternoon, transfer to Cortona considered the main cultural and artistic center of the Val di Chiana after Arezzo. The prevailing character of Cortona's architecture is medieval with steep narrow streets situated on a hillside (altitude 600 metres), embracing a view of the whole of the Valdichiana.
Two of the churches in Cortona are prime examples of two different principles of Renaissance construction.
Day 6 / Spello
Departure to Spello. After arrival, check in at the Hotel Il Cacciatore.
In the afternoon, guided visit of the village.
Day 7 / Assisi and Deruta
Excursion to Assisi. A visit to the magnificent Lower and Upper Basilica where the mortal remains of St. Francis lies. Here one can see the blossoming of Art and Faith in the 13th and 14th century’s frescoes by Cimabue, Giotto, Simone Martini, Ambrogio Lorenzetti and other great artists illustrating Christ, St. Francis and other Saints’ lives and miracles.
In the afternoon, transfer to Deruta, a pretty stone hill town. At first glance it looks like any other medieval town dotting the countryside. But when the visitor enters through the ancient gates he will see that this hamlet is distinct: its sole industry is ceramics.
There are nearly two hundred workshops and stores, along with a school for Ceramic Arts and a Ceramics Museum, dedicated to Deruta's thriving artistic tradition. The Moorish design influences are retained even today in many traditional patterns. All of the patterns are brilliantly colored, highly decorative, hand-painted masterpieces.
Day 8 / Gubbio and Spello
Excursion to Gubbio. Guided visit of the town reach of historical attractions spanning many periods. The 14th-century Palazzo dei Consoli houses Umbria’s largest collection of Roman artifacts. Afternoon free time at Spello.
Day 9 / Departure to US
Transfer, by private motor coach, to Rome, flight back to Boston.

Dates and Price details

Dates Price details
Avaliable year around From *$ 2019.00 per person – Land only
Single supplement $ 519.00


  • 7 Nights hotel accommodation
  • 7 Buffet breakfasts
  • Private guide at Anghiari, Citta’ di Castello, Montone, Arezzo, Cortona, Assisi, Deruta, Gubbio
  • Entrance fees at sites visited
  • Private motor coach for transfers and excursions as per program
  • City taxes


  • Air valid for departures from Boston. All major gateways are available. Round trip air transportation includes air taxes and fuel surcharge (subject to change).

Map – The Medieval Villages of Tuscany & Umbria

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    I want to start off by saying thank you for making the accommodations, they’ve been lovely. Florence was more than we could imagine, the hotel and staff were exceptional. As was Venice, so far I love Venice more than any city so far.  Thank you very much for helping to change things around for us. The room they moved us to in Rome is sooooo much better. The window lets in fresh air and there’s more space. Roberto, the manager, says hello. He said he is friends with your father and was pleased to help us out. Our day is off to a much better start and I feel so much better. Grazie Mille.


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  • Good day Luca,
    Recently you put together a vacation for my clients Stanley and Katherine  and I would like to thank you so much for making their vacation a very memorable one. I received a call from them and they were so Pleased and excited about how they loved it from start to finish. Your choice in hotels and the transportation provided from one city to the next with the private drivers was such a pleasant experience for them. They said everything was perfect and your drivers so pleasant.

    So once again, Thank you!