Welcome to Val di Chiana


If you're in the valley on the third Sunday in June, don't miss the Palio dei Rioni that sees jockeys on horseback race around Piazza Garibaldi in Castiglion Fiorentino – like Siena's palio on a smaller scale.


Top experiences in Val di Chiana

Val di Chiana activities

$1153.15 Multi-day & Extended Tours

8- Days Best of Italy Trip from Rome

Day 1: RomeAfter meeting your driver at the airport, you'll be transferred to your hotel. Overnight stay.Day 2: Rome - Assisi - Siena - FlorenceDeparting at 7:15 am from your hotel, arrive in Assisi, ready to explore, at your own leisure. Take your time to visit the basilica of St. Francis, and then have free time for lunch (not included). Board on the bus to reach Siena. Next, you will continue on to Florence, where you will check in at your hotel before enjoying dinner.Day 3: FlorenceAfter breakfast, spend the day exploring Florence. Lunch in a typical Tuscan restaurant in Piazza Santa Croce. Spend the afternoon strolling the cobblestone streets of Florence on your own or take a short trip to Pisa (optional), one of the four main historical Marine Republics of Italy. There, you will tour the Piazza dei Miracoli with the Duomo, Pisa's symbol "the Leaning Tower" and the Baptistery. Dinner at leisure, overnight stay in Florence.Day 4: Florence - Bologna - Padua - VeniceAfter breakfast in Florence, departure to Bologna. There, you will discover the elegant city centre. From Piazza Malpighi, walk to Piazza del Nettuno and Piazza Maggiore (Neptune square and Major square), then King Renzo's Palace; Palazzo Podestà and the basilica of San Petronio. In the afternoon, continue toward Padova, with Sant'Antonio Basilica. Later in the afternoon, arrival in Venice. Check in at your hotel for dinner and overnight stay.Day 5: VeniceAfter breakfast, enjoy your private water-taxi transfer to Piazza San Marco, with "Skip the Line" tickets to visit the splendid St.Mark's Basilica and, after this, check out the most iconic places of the "Floating City": the Palazzo dei Dogi, symbol of Venice's glorious past, the legendary "Bridge of Sighs". Spend the afternoon roaming along Venice's canals at your leisure and then return to the hotel and overnight.Day 6: Venice - Montepulciano (Tuscany wine region) - RomeAfter breakfast, departure from Piazzale Roma heading to Tuscany. Proceed to Val di Chiana with a stop in Montepulciano, a medieval town rich in history and art. Lunch in a typical restaurant included, Spend the afternoon discovering Montepulciano at your own pace, enjoying lunch in a typical restaurant and free time for shopping. In the evening, you will arrive in Rome to check in into your hotel.Day 7: RomeAfter breakfast, departure from the hotel for the included tour of the Vatican Museums, Sistine Chapel and St. Peters's Basilica with our exclusive "Skip the Line" access. Afterward, enjoy the rest of the day to explore the city at your own leisure or get any one of our selected tours for the afternoon or at night! Overnight stay.Day 8: RomeAfter breakfast, transfer to the airport.

$6.85 Sightseeing Tickets & Passes

San Biagio in Montepulciano Entrance Ticket

Visit: Tempio di San Biagio, Montepulciano, TuscanyDiscover the masterpiece of architect Antonio da Sangallo the Elder, where the Val d'Orcia merges into the Val di Chiana. Montepulciano (province of Siena), whose palaces, churches, and town planning reflect the High Renaissance in a kind of open-air museum, has often been called the "pearl of the 16th century." In particular San Biagio church is considered one of the most perfect examples of High Renaissance architecture. Don't forget to add it to your itinerary! Please note that: • This is not a guided tour • There is not a meeting point • Ticket includes use of audio guide (25 minutes). • Free Admission for children under the age of 6

$50.24 Food, Wine & Nightlife

Olive oil tasting in a real crusher

Cortona is a beautiful town in the province of Arezzo, in Tuscany, Italy. It is situated 494 meters above sea level near the Monte Sant'Egidio, between Val di Chiana and Val Tiberina. Cortona holds within its walls a number of historic and religious buildings that testify to the illustrious past and its importance in the history of the region. It is the main cultural and artistic center of the Val di Chiana after Arezzo.Discover this amazing city and live an authentic culinary experience with a local. Meet your friendly guide, Brunella, and visit a real crusher. The oil tasting is like wine, you can taste 3 different types of oil. Enjoy the special location, the crusher, and listen to the history of olive oil making in Brunella's family. Take a sip of homemade white and red wine and enjoy the rural atmosphere.Don't miss this exclusive experience in Cortona!

$90.20 Food, Wine & Nightlife

Special dinner in Montepulciano with a unique view

Standing high atop a hill in southern Tuscany not too far from Siena, Montepulciano is a medieval town of rare beauty. The city, full of elegant Renaissance palaces, ancient churches, charmingsquares and hidden corners, boasts vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys that surround it.Live an authentic culinary experience in this amazing city. Meet Giulia, your friendly local chef, and enjoy a journey through Italian tastes in a wonderful location. Here's a sample menu:Starters- artichoke, primo sale cheese, strawberries- zucchini cream with mint, vegan homemade yogurt, millet muffin- beans salad, focaccia breadMain courses- spaghetti with chicory, Marzolino cheese fondue- gnocchi with sage and garbanzo beans cream with saffron, hazelnuts- marinated tofu, apple and mustard cream, almonds- special roll and pumpkin' dip- futomaki polenta with spinach and pecorino cheese, Brasil toasted nutsDesserts- meringa-lemon curd bisquit- dark chocolate soufflé- coconut mousee with cocoa and goji berry You can choose 4 dishes, and there's the option of gluten free or vegan menu.Don't miss this special experience in Montepulciano!

$170.12 Food, Wine & Nightlife

Montepulciano: Tuscan Food Cooking Class with a Local

Standing high atop a hill in southern Tuscany, Montepulciano is a medieval town of rare beauty. The city, full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners, boasts vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys that surround it.On this tour, discover traditional Tuscan cuisine on a farm. Collect the ingredients from the garden and discover recipes and traditional flavors. Learn the secrets behind typical Tuscan recipes while toasting with a glass of Rosso di Montepulciano DOC wine.Here's a sample menu:• Crostini• Fresh pasta rolled by hand• Seasonal and fresh vegetables• Typical dessertOnce the work is complete, take a seat and enjoy the fruits of your labor in a friendly atmosphere. Get ready for an amazing experience in Montepulciano!

$167.83 Cultural & Theme Tours

Private The Essence of Tuscany: Chianti Classico, Montalcino, Montepulciano

ItineraryThis is a typical itinerary for this productStop At: Piazza Matteotti, Greve in Chianti, TuscanyEnter the heart of real Tuscany with medieval villages of incomparable charm, an ancient farming tradition producing wine, cheese, cold cuts and excellent meat renowned and appreciated all over the world even today. The beauty of the landscape declines harmoniously where nature and the works of man have lived together for centuries in an unbeatable balance. Through the hilly expanses of the old vineyards and olive groves, which characterize the splendid Chianti territory, you reach Greve where you will enjoy the charm of its historic square flanked by open galleries and wander around the characteristic shops of local handicrafts and the typical Chianti products.Duration: 30 minutesStop At: Rocca di Castellina, Castellina In Chianti, TuscanyYou continue with a stop in Castellina, a characteristic ancient hamlet perched on a hillDuration: 30 minutesStop At: Chianti Road, TuscanyJust outside the village, in one of the most famous vineyards of the area, you will be guided through a tasting of different wines of the Chianti area, extra virgin olive oil on Tuscan bread, Vin santo with "cantuccini" locally producedDuration: 30 minutesPass By: Monteriggioni, Monteriggioni, TuscanyProceeding along a panoramic road you can admire the picturesque village of Monteriggioni, a small medieval jewel still surrounded by its ancient walls. Stop At: Val d'Orcia, TuscanyFurther on, the unmistakable clay landscape of the Crete Senesi, a hilly desert territory that rouses unforgettable feelings. Continuing, you reach an area that contrasts incredibly with the Crete territory, immersed in the green Val d'Orcia, UNESCO heritage, a harmonious landscape of hills dotted with cypresses, interrupted by castles, churches, ancient villages of Etruscan origin and farms that accompany the route of the famous "Via Francigena". Here, in a historic farm, you will be served a guided lunch-tasting of the renowned Rosso di Montalcino and Brunello, a large selection of typical products of the territory and a delicious homemade fruit pie. All this is followed by a visit to the cellars and some leisure time to enjoy the natureDuration: 2 hoursStop At: Fortezza di Montalcino, Montalcino, TuscanyYou then make a stop in the medieval village of Montalcino, with its boundary walls enriched with towers and the imposing fourteenth century fortress, offering one of the most beautiful views onto Val d’Orcia. Montalcino also has narrow streets with dozens of wineries and artisans’ shops selling products of the territory. Duration: 30 minutesStop At: Piazza Grande a Montepulciano, Montepulciano, TuscanyLastly, after a short journey on a panoramic road, you reach Montepulciano, enclosed by fortified walls and perched on a hill 600 meters above sea level between Val d’Orcia and Val di Chiana. The town is renowned for its Noble wine obtained from the surrounding vineyards.Please note that the order of the visits may changeDuration: 1 hour 30 minutes

Val di Chiana in detail