The unique charm and ancient monuments of Assisi & Cortona are truly something to behold on this guided tour through the idyllic crossroads of the Tuscan and Umbrian countryside. See where they filmed ‘Under the Tuscan Sun’, and learn about the life of Saint Francisco as you meander through some of the oldest medieval streets.

From: $680.00

SKU: SI-010-DT Category: Tags: ,

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This unique journey is perfect for small town explorers

Two stunning regions of Italy, two picturesque village towns, one perfect day.

Setting out from Florence or surroundings, a private driver will take guests through the stunning Tuscan landscape through the neighboring Umbria region. Therein lies the jewel of Assisi. An ancient town that spirals around a hill, a stroll along its walkways offers stunning vistas at each turn.

To explore are the many poignant dedications and historic monuments honoring the town’s most beloved resident of all time, St. Francis. Guests will have free time to visit the traditional artisan stores, the Temple of Minerva, the stately Basilicas and Cathedral or perhaps even the imposing bastion of Rocca Maggiore perched atop the town.

The group will then proceed back to the Arezzo area of Tuscany for a visit to the charming village town of Cortona. There is free time to stroll along the cobbled streets to explore the boutiques or perhaps visit the Etruscan Academy Museum that harks back to the origins of this historic village.

Lunch can be enjoyed in one of the traditional eateries of the town, possibly whilst taking in spectacular views of the Val di Chiana laid out beyond. Guests will be able to relax on the return drive to Florence whilst submerged in the picturesque Tuscan landscape.

What is it that makes Siena and San Gimignano so extraordinary?

Bordering the Tuscan region is the lush Umbria region, in which lies Assisi. Its history stretching back to around 1000 B.C., it has a uniquely spiritual feel that goes beyond the presence of many churches, temples and Basilicas.

Assisi holds the unmissable Basilica di San Francesco, frescoed by renowned artists including Giotto, whose depiction of St. Francis’ life dates back to the 1300s. There is Basilica di Santa Chiara where the saint’s body is displayed and the Baroque Basilica Santa Maria degli Angeli where St. Francis died, his rope belt now on show.

Contrasting spiritual Assisi is the cultural and artistic Cortona. A quintessential Tuscan town, it is dissected by one main street from which stretch out a number of quaint alleyways buttressed by stunning Tuscan views.

The Etruscans named the area Curtun some 7 centuries B.C. After later falling under Roman rule, Cortona then passed through various ruling powers throughout its long history. What stands testament to its past is predominantly Medieval, although parts of Etruscan walls also still stand.

Cortona’s main sites include Etruscan tombs, the Duocesan Museum featuring panels by Fra Angelico, the splendid Piazza Garibaldi, the Palazzo Casali holding the Etruscan museum, and the domed Santa Maria Nuova church by Vasari from 1554.


  • Cross two splendid regions of Italy: Tuscany and Umbria.
  • Enjoy free time exploring the picturesque villages of Cortona and Assisi.
  • Dine on Tuscan delicacies in Cortona.
  • Be collected directly from Florence or other central location upon request.

So that this tour may be tailored to individual preferences, any entry costs, food and beverages are additional, to be paid by guests directly on the day. This ensures our guests may experience the best of the region exactly as they wish. Our driver would be happy to provide dining suggestions.