Enjoy a full-day private tour through the heart of Tuscany, visiting the stunning cities of Siena, San Gimignano, and the renowned Chianti Classico wine region.
Your adventure begins in Siena, where you can explore at your own pace the magnificent Siena Cathedral and the famous Piazza del Campo, home to the thrilling Palio horse race. Afterward, head to San Gimignano, the “Town of Towers,” known for its medieval charm and sweeping views of the Tuscan countryside. Enjoy the freedom to stroll through its picturesque streets and visit local artisan shops on your own. In the afternoon, journey into the Chianti Classico region, where you’ll visit a local winery for a wine and olive oil tasting, sampling some of the finest Chianti Classico wines and local olive oils.
Exact time will be provided in final documents. Pick up at your hotel.
- Transportation
- Private English-speaking driver at disposal for 9 hours
- Wine tour, wine and extra virgin olive oil tasting and a snack
- Gratuities (optional)
- Tour Guide
- Lunch
- Entrance into churches requires a dress code - shoulders and knees must be covered.
Traveling through the hills of Crete Senesi, just around an hour from Siena, you will discover the ancient cities of Arezzo and Cortona. On this full day tour, you will first stop in Arezzo, an ancient city with Etruscan roots, famous for its stunning works of art by Piero della Francesca and Cimabue. Visit the Basilica of San Francesco, Piazza Grande, and the medieval Church of San Domenico, home to Cimabue’s remarkable crucifix. Stroll through charming antique shops and boutiques, soaking in the city's rich artistic heritage.
Next, travel through the picturesque Val di Chiana to Cortona, a hilltop town offering sweeping views of the valley below. You may explore the Sanctuary of Santa Margherita, perched at the highest point of the village, and take in the panoramic scenery. Descend into the city center, where you can visit the tranquil Eremo delle Celle, a 13th-century convent founded by St. Francis. As you arrive in the main square, admire the historic Town Hall and Clock Tower. You’ll have time to shop, capture stunning photos, and soak in the timeless beauty of Cortona.
Exact time will be provided in final documents. Pick up at your hotel.
Take an excursion to a land of ancient wine making traditions, unique landscapes, medieval castles and abbeys, and gorgeous vineyards surrounded by woods, olive groves and cypress trees. A region filled with exceptional beauty – Chianti. First stop along the winding hills of the Chianti Castles Route is the beautiful medieval town enclosed by massive walls, Radda in Chianti. This magnificent town is the perfect place to enjoy good wine and embrace the natural picturesque landscapes that surround you. Next is the ancient village of Castellina in Chianti, a town rich with history as if time itself has stopped.
In this beautiful region you will visit one historical wine estate in the heart of Chianti. Here you will be guided through the estate cellars and enjoy a wine tasting.
Exact time will be provided in final documents. Pick up at your hotel.
Traveling through the Tuscan hills with your private English-speaking driver, you will visit the ancient cities of Perugia and Assisi on your own.
Upon arriving in Perugia, you will cross ancient archaeological finds and the brick vaults of the Rocca Paolina (a fortress constructed in the mid-16th century); then travel up to the Carducci Gardens overlooking the entire valley. You will discover the main sights of the historic city center on your own including Corso Vannucci, IV Novembre Square with its gorgeous Fontana Maggiore, Palazzo Dei Priori, and the amazing San Lorenzo Cathedral.
Then continuing on your journey, you will arrive in Assisi: a gorgeous town with 14th century streets, squares, and churches. Stop for a delicious lunch at a traditional restaurant in this ancient village and have the chance to discover on your own the Basilica of St. Francis overlooking the city and entire valley. It is truly a masterpiece to treasure, consisting of two churches built one on top of the other, and the amazing art works of Cimabue, Simone Martini, Lorenzetti, and Giotto. You will also have the chance to admire the Cathedral of San Rufino and the Church of Santa Chiara, both filled with amazing history. While heading back to Siena, you may stop at the Basilica of Santa Maria degli Angeli which houses the sacred Porziuncola where St. Francis of Assisi himself lived, and at the Transito Chapel where St. Francis died.
Exact time will be provided in final documents. Pick up at your hotel.
