Is the tour fully private?

Yes, this is a private VIP tour, designed for your group alone with a dedicated driver-guide.

Are food allergies and dietary restrictions accommodated?

Absolutely. Let Under The Tuscan Sun Tours know in advance to customize your lunch.

How much walking is involved?

Moderate walking includes city streets and climbing the Duomo and San Gimignano’s towers.

What languages does the guide speak?

The driver-guide speaks English to provide rich cultural insights throughout the tour.

Is transportation included?

Yes, private transportation from your Florence address and back is included.

Can the itinerary be customized?

While the tour follows a set itinerary, special requests may be possible when arranged in advance.

Tuscan Wine & Culture Tour with Under The Tuscan Sun | Farm | Private

Set your sights on Tuscany, Italy’s rolling heartland where medieval architecture meets sun-drenched vineyards. Under The Tuscan Sun Tours offers a private, nine-hour journey weaving together history, local flavor, and landscape in a seamless story. This tour invites travelers to start in Florence before diving deep into the iconic sights and tastes of Siena, Monteriggioni, San Gimignano, and Chianti's famed vineyards.

The day begins with a pick-up right at your address in Florence, easing you into the pace of Tuscan life. First stop: Siena. Known for its well-preserved Gothic grandeur, Siena’s Duomo commands attention with its striking striped marble facade and intricate interior mosaics. A climb up the Duomo’s terraces rewards you with a commanding view of the city’s winding streets and the Campo, the historic square home to the Palio horse race, a centuries-old tradition pulsating with local pride.

Next, the tour rolls into the Chianti region, where the landscape transitions into a peaceful patchwork of grapevines and olive groves. Here, lunch is more than a meal — it’s an immersion. Savor traditional Tuscan dishes paired with estate-produced wines and olive oils at a boutique winery, an experience emphasizing terroir and tradition.

Afternoon brings the medieval charm of San Gimignano into focus. Famous for its soaring towers, climbing the Great Tower offers panoramic vistas of the surrounding countryside. Don’t miss a tasting of the village’s award-winning gelato — a sweet contrast to the robust reds of the vineyard.

The finale unfolds at Michelangelo Plaza, just outside Florence, where sweeping views of the city’s rooftops and the Arno River create a perfect closing tableau. Under The Tuscan Sun distinguishes itself by blending expert local knowledge with seamless private transport, ensuring each moment is rich and relaxed. This tour is far more than sightseeing—it’s a paced immersion into Tuscany’s soul, perfect for those who appreciate culture, cuisine, and landscape in equal measure.