“The Cultural Landscapes of Tuscany” Tours: Val d’Orcia, Casentino Valley, Medici Villas and Gardens

Discover Val d’Orcia, Tuscany: Private Day Tour from Florence

The region of Val d’Orcia in southern Tuscany was inscribed by UNESCO as a “Cultural Landscape” in 2004 both for its natural and cultural heritage. The Val d’Orcia is the quintessential Renaissance landscape with its hilltop towns, vineyards, olive groves, and rows of Cypress trees punctuating the landscape.

Our architecture, landscape, and cultural heritage day tour takes us to the hilltop towns of Montepulciano, Pienza, and Montalcino. We leave from Florence with a private car service crossing through the Sienese landscape to the unique landscape of the Val d’Orcia. We stop in the charming medieval hilltop town of Montepulciano to experience its architecture, cultural history, and local food and wine traditions. This picturesque town is the setting for our lunch where we are introduced to the traditional foods of the area including the famous wine Nobile di Montepulciano.

From there we make our way through the scenic cultural landscape of Val d’Orcia renowned for its ever changing palette of colours depending on the season to the idealized Renaissance hilltop town of Pienza where we visit the garden and palace of Pope Pio II. We continue our journey through the panoramic landscape of the surrounding hills towards Montalcino, to experience the specific habitat “terroir”, for a personalized wine tasting of the celebrated Brunello di Montalcino at a local vineyard and cantina renowned for its sustainable and traditional cultivation of Brunello, one of Italy’s most famous wines.

As an alternative to the wine tasting, we may continue towards the beautiful Medieval hilltop town of Montalcino stopping along the way at the 12th century Abbey of Sant’Antimo in time to catch the last rays of sun on its Romanesque facade.

Experience the singular aesthetic beauty of the Renaissance landscape of Valdorcia.

Price available upon request.

Val d’Orcia, Tuscany, Private Two Day Tour

We also offer a two day tour to Val d’Orcia, which includes the above itinerary, and staying overnight at a 15th century monastery (known for its frescoes and garden), now an agriturismo, a ‘magical place’ near Pienza. On the second day of the tour we visit the famous and elegant garden of ‘La Foce’ designed by the landscape architect Cecil Pinsent for Antonio and Iris Origo. The two day tour is seasonal.

Price available upon request.

Tuscany Cultural Heritage Excursions

7 Days, 7 Nights Superior Accommodation
Orientation Wine and Cheese
Breakfast Included Each Day
6 Lunches Included
6 Dinners Included
Wine tastings
Museum and Site Fees Included
Transportation to Sites

The Florence and Tuscany walking tour, which is 7 days and 7 nights is an inspiring and immersed ‘experience of place’ of the architecture and cultural history of the historic centre of Florence and the Val d’Orcia region of Tuscany. Val d’Orcia is UNESCO World Heritage region famous for its wine and culinary traditions.

The walking tour will begin in Florence, the birthplace of Renaissance art and architecture, and a World Heritage site. We will stay at a charming hotel in the historic centre of the city overlooking the famous Duomo, and minutes from the Ponte Vecchio and the Arno River. We will spend two full days in Florence visiting the historic borgos (neighbourhoods) of the city with their architectural, artistic, and artisan treasures, including a visit to Brunelleschi’s Duomo and the Galleria Uffizi. Our excursions will also provide ample opportunity to sample authentic and regional cuisine for lunch, caffé pauses, and dinner at local spots that are frequented by the Florentines. The second day will be dedicated to one of Florence’s most famous citizens, Michelangelo, his sculpture and architecture. This will be followed by a winetasting at the restaurant of one of Florence’s most famous families and wine producers. Time will be reserved for shopping in local markets, artisan shops, and boutiques. The city is also well-known as one of Italy’s Fashion centers.

We will then travel to the scenic Medieval and Renaissance hilltop towns of Tuscany, including Cortona, San Gimignano, Montepulciano, Montalcino, and the idealised Renaissance town of Pienza participating in the rich cultural heritage of these hilltop towns. Our tour takes us through the Val D’Orcia, a UNESCO World Heritage region famous for its landscape, orchards, gardens, and wine. Our architectural and cultural experience of this region will be punctuated with visits to some of the region’s most famous vineyards as well as lunch and wine tasting at one of the most celebrated cantinas in the area.

In the foothills of the Val D’Orcia we will spend two nights at an agriturismo, formerly a 15th century monastery, with a panoramic view overlooking the surrounding countryside, described by visitors as “…a jewel, a magical place.” On the last day of our journey we will wind our way back through the scenic hills of the Val d’Orcia to Florence culminating our tour with a farewell dinner.

Small groups of 10 people. All transportation between sites by private car.

Price available upon request.

Click on tour calendar for dates.

Click here for full itinerary …

Booking terms and conditions

For Alumni and Friends please click here for Booking Terms and Conditions …

Travel partner with UBC Alumni Association.

For further information on itinerary and price contact: info@culturalheritagetoursitaly.org