Where does the tour start?

Meeting point is communicated after booking: A ser comunicado após a reserva.

Are wine tastings included?

Yes—tastings at a selected Montalcino winery are included; lunch is optional and available for an extra charge.

Can we visit Siena Cathedral (Duomo)?

Yes—visiting the Duomo requires an extra hour (+€88). Ticket handling can be added (+€11) or you can purchase entry online.

What is the group size?

Groups range from 1 to 15 people, and the tour is private to your party during the booking.

Are transfers from Florence provided?

Meeting logistics and transfers are arranged after booking; the operator will confirm pickup or meeting details.

Is the tour suitable for children?

Children are welcome but expect walking on cobbles and stairways; inquire about winery policies for minors when booking.

Private Montalcino and Siena Tour: Brunello Tastings and Medieval Siena in 6 Hours

On a clear Tuscan morning, rolling hills stitched with cypress and vines lead from Florence toward two of the region’s most compact, character-rich towns: Siena and Montalcino. The Tour Montalcino e Siena – privativo is a six-hour private drive-and-walk experience that collapses centuries into a single day of brick streets, Romanesque cathedral facades and Brunello tastings. It begins with Siena’s medieval core, where narrow alleys open onto the fan-shaped Piazza del Campo, the stage for the fiercely contested Palio and a place where community identity is still visible in painted contrada flags and carved stone. In Siena, this itinerary highlights the Basilica of San Domenico, the house and chapel of Santa Caterina de Siena, viewpoints popular with photographers, and the Duomo precinct including the Museo di Santa Maria della Scala — sites that map the city’s artistic lineage from Duccio to Simone Martini and its civic life centered around the Monte dei Paschi di Siena. If you want to enter the Duomo, note that the tour can extend by one hour for access (additional fee applies; see booking details). The afternoon shifts into the Brunello country of Montalcino, a small hill town of roughly 5,900 residents whose compact fortress and stone streets slope toward vineyards. Here, the tour includes a visit to a select winery chosen for quality and context, with guided tastings of Brunello di Montalcino—wines rooted in Sangiovese Grosso grapes grown on galestro and alberese soils—and an explanation of how terroir, vine age and cellar practice shape each vintage. Optional lunch at the winery can be arranged to pair local pasta and dessert with the wines. What makes this private tour special is its combination of deep cultural layering and sensory reward: medieval civic drama in Siena followed by the slow, gustatory focus that defines Montalcino. The route shows distinctive geology and cultivated landscape—olive groves, stone walls and vineyards cut into clay-limestone slopes—and includes both iconic monuments and quieter corners favored by locals. Logistics: meeting point is A ser comunicado após a reserva. Group size ranges from 1 to 15 people. Languages and exact winery selection are confirmed after booking. Bring comfortable shoes for cobbled streets, a charged camera, and an appetite for history and wine. A local guide will shape the day to your interests, whether you want more time in artisan shops off Via di Città, history about Siena’s Etruscan and Roman roots and the legend that Siena was founded by Sènio, son of Remus, or longer tastings at a cellar. If you wish to visit the Duomo, expect the tour to add one hour (+€88) and ticket handling can be added (+€11) or bought online. Small groups make it easy to tailor pacing and pairings.

Private Montalcino and Siena Tour: Brunello Tastings and Medieval Siena in 6 Hours

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