Rome to Siena & San Gimignano: Tuscany Wine Tasting Tour

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Free cancellationExcellent quality

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Duration10h

GroupUp to 12

LanguagesEN · PT +3

PickupAt your hotel

Medieval towers, Chianti cellars, and 10 wines in one day from Rome

You visit Siena's medieval center and Piazza del Campo, explore San Gimignano's walled streets and towers, then taste 10 wines and eat lunch at a working estate near the town. Hotel pickup from central Rome is included, as is your guide for the whole day. The fixed schedule means you see both cities and the cellar without arranging transport or timing anything yourself.

10h

Step-by-step itinerary

Visit Siena and San Gimignano with wine tasting

Visit Basilica of San Domenico
See Duomo di Siena exterior
Explore Piazza del Campo
Walk medieval streets of San Gimignano
Visit San Gimignano old center
Tour Tenuta Torciano estate
Taste 10 wines and local products

The Experience

The minivan picks you up at your hotel in central Rome while the light is still soft. By the time you reach the Chianti hills, the landscape has already shifted—rolling vineyards, cypress trees, the kind of view that makes you understand why people write about Tuscany instead of just visiting it. The drive takes a few hours, but it's not wasted time; you're moving through the thing itself, not toward it.

Siena arrives first. Your guide walks you through the historic center on foot, and you stand in Piazza del Campo—the shell-shaped square where the Palio horse race happens twice a year, July and August, when the whole plaza gets covered in earth and the neighborhoods send their riders at a gallop. It's empty when you're there, but the shape of the space tells you what it's for. You'll see the Duomo, the striped marble cathedral built between 1214 and 1263, and the Basilica of San Domenico on the slopes above. Two hours here, which is enough to walk the medieval streets without rushing, to buy a panforte or ricciarelli—the local sweets Siena is known for—and to sit for a moment before moving on.

San Gimignano comes next, and it's smaller, walled, with towers still standing that medieval families built to show their wealth and power. The town is called "The City of the Hundred Towers" though there are fewer now, and it's a UNESCO World Heritage Site. You walk the old center, and then the real reason for the day begins: Tenuta Torciano, a wine estate near the town where thirteen generations of winemakers have worked the same land. You visit the cellars where they process grapes and age wine, and then you sit down to taste. Ten different wines—reds, whites, the local Vernaccia di San Gimignano—paired with lunch made from local products. Oil, cheese, bread, the kind of meal that tastes like it came from the place you're standing in. It's not rushed; you have time to taste, to ask questions, to understand what you're drinking instead of just swallowing it.

The return to Rome happens in the afternoon. You're back at your hotel by evening, and the whole day—the drive, the two cities, the cellar, the lunch, the wines—is included. No separate tickets to buy, no figuring out the train schedule, no negotiating with a taxi driver at the end. Hotel pickup and drop-off are part of it, and the minivan is air-conditioned, which matters on a long day in summer.

What’s included

Your day includes free hotel pickup and drop-off in an air-conditioned minivan, a professional tour guide for the entire trip, two hours exploring Siena's historic center with visits to Piazza del Campo, the Duomo, and the Basilica of San Domenico, a walk through San Gimignano's medieval streets, entry to Tenuta Torciano estate and wine cellars, a tasting of ten different wines, and lunch with local products including oil, cheese, and bread.

Good to know

Easy physical levelStroller friendlyInfant seats availableInfants must sit on laps

Operated by Welcome Italy

Is this one for you?Book this if you want to see two major Tuscan cities and taste wine at a working estate without arranging separate transport, entry tickets, or a lunch reservation—the full-day structure and included pickup handle all of that, leaving you to focus on the places and the wine.