Connecting with Tuscany

While Santolina feels wonderfully secluded, you're in the heart of one of the most vibrant and culturally rich regions in the world. Easily access many of Tuscany’s most famous historic medieval cities, and explore smaller towns yet to be discovered by the common tourist.

Prefer a cosmopolitan trip steeped in history? Visit Siena and Florence, 30 minutes to 1.5 hours away, respectively.

Prefer to follow your appetite? There are exceptional restaurants just minutes away, and many Michelin-starred kitchens less than an hour from the villa.

For those craving nature, the Riserva Merse offers scenic trails for hiking and exploring. Or explore the Maremma and relax on the beach, as the Tuscan coast is just an hour away, offering warm clear water, sandy beaches and medieval seaside towns.

From scenic hilltop villages to backcountry rocky roads, we can guide you through Tuscany at your pace and in your style. Whatever your preference, one thing remains certain—Santolina is your perfect starting point.

A historic Italian hillside town with medieval buildings, church towers, and lush greenery, illuminated by golden sunlight.
A panoramic view of a historic Italian city square with a tall clock tower, surrounded by old buildings with tiled roofs.
Beach with turquoise water, white sand, beach chairs, umbrellas, and people swimming and relaxing.

Seasonal Events

People harvesting bunches of dark purple grapes from a grapevine in a vineyard.

WINE HARVEST (September - October)

In the fall, guests can join our neighboring winery and participate in the harvesting and stomping of the grapes. Or just enjoy the view with a glass of wine in hand.

People riding horses at a bullfighting ring, with a large crowd of spectators in the stands, some wearing colorful costumes. The riders are dressed in vibrant, traditional outfits, and some are wearing helmets. The scene appears to be a part of a cultural or sporting event involving horseback riding.

PALIO DI SIENA (July, August)

This historic bareback horse race is held twice a year in July and August in the main piazza of Siena. With origins in the 12th century, the current race has been held since 1633, and is an intense rivalry between the contrade (parishes) of Siena. It is a must for anyone who truly wishes to understand Tuscany.

A man participating in a barrel rolling race during a street festival, with a crowd of onlookers behind a barricade watching and taking photos.

BRAVIO DELLE BOTTI (August)

This Montepulciano tradition features 16 competitors, two from each district, racing to push 80-kilogram wine barrels on an uphill path over a kilometer long, from the Colonna del Marzocco to the cathedral in the Piazza Grande. It celebrates the vibrant and distinct histories, symbols, colors, and achievements of the eight districts.

Two musicians playing jazz instruments on stage at a jazz festival with a black backdrop and the words 'SENA JAZZ' in large white letters.

SIENA JAZZ FESTIVAL (July -August)

Come appreciate jazz in the Italian style. During the summer, the city hums to the rhythm of the bass as the Siena Jazz University performs concerts and competitions throughout the streets.