Experiences in Siena

Medieval Siena and the rolling hills of the Val d'Orcia

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Siena

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Siena

6 experiences and tours

Supercar, Wine Tasting & Castello di Brolio Experience

New

A private afternoon and evening supercar experience through the Chianti countryside, combining scenic driving, wine tasting and Tuscan hospitality. The experience starts from Villa Ermellina in Siena

7 Hours

€2,020Per Group

Supercar & Wine Tasting Experience at Casanova di Neri

New

A private one-day experience combining the emotion of driving a supercar through the Tuscan countryside with a guided wine tasting at Casanova di Neri, one of the most renowned wineries in Montalcino.

7 Hours

€2,030Per Group

Supercar Experience in Siena and Val d'Orcia with Lunch

New

Driving a Supercar through Val d'Orcia and have lunch in one of the best meat restaurants

6 Hours

€1,940Per Group

Classic Car Tour Experience in Val d'Orcia with Lunch

New

Experience the thrill of driving a supercar through the enchanting Val d'Orcia, followed by an exquisite lunch at a premium meat restaurant - the epitome of refined indulgence.

7 Hours

€1,050Per Group

Classic Car & Wine Tasting Experience at Casanova di Neri

New

Indulge in an exclusive one-day journey through Tuscany, driving a supercar and savoring a guided wine tasting at Casanova di Neri winery, beginning from the elegant Villa Ermellina in Siena

6 Hours

€980Per Group

Classic Car, Wine Tasting & Castello di Brolio Experience

New

A private afternoon and evening classic car experience through the Chianti countryside, combining scenic driving, Tuscan heritage, wine tasting and refined hospitality.

8 Hours

€2,000Per Group

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Frequently asked questions

Siena's standout experiences combine the medieval city with the Val d'Orcia countryside — classic-car and supercar drives through the wine hills, tastings at historic estates such as Casanova di Neri, and guided walks of the old town and Piazza del Campo.

Yes. Our Siena and Val d'Orcia experiences are led by local guides and run in English, with small groups and hotel-friendly departure points.

The Val d'Orcia begins just south of Siena; most drives and wine experiences reach the vineyards and villages within 30–60 minutes.

Siena is the medieval jewel of central Tuscany and the gateway to the Val d'Orcia — a UNESCO landscape of cypress-lined roads, hilltop villages, and celebrated vineyards. Our experiences pair the city's Gothic old town with unforgettable drives and wine tastings across the surrounding countryside.

About Siena

Wrapped in medieval walls and centred on the shell-shaped Piazza del Campo, Siena is one of Italy's best-preserved historic cities. Beyond its cathedral and narrow contrade streets lies the Val d'Orcia, where estates like Casanova di Neri and Castello di Brolio produce some of Tuscany's finest wines. Whether behind the wheel of a classic car, riding in a chauffeured supercar, or tasting Brunello at a historic cellar, Siena is the perfect base for exploring the Tuscan good life with expert local guides.