Siena, San Gimignano & Chianti Full-Day Tour
- Duration
- 9h
- Type
- Small group
- Category
- Siena + San Gimignano + Chianti
- Cancellation
- Free, up to 24 hours before
About this experience
What to expect
Siena, San Gimignano and Chianti form a natural trio in central Tuscany, and together they tell a single story: how a landscape of pilgrims, merchants, rival city states and farmers produced the Tuscany people travel to see. This page follows that story through history and legend, which is a different way of looking at the region from a list of sights.
A road that built the towns
Both Siena and San Gimignano grew along the Via Francigena, the pilgrim road that ran from Canterbury to Rome. Travellers on foot needed food, lodging and money changers, and towns along the route became prosperous. San Gimignano's towers and Siena's banking families belong to this world of medieval trade. Today the Via Francigena is walked again as a long-distance route, and you can still meet walkers with backpacks on Tuscan roads.
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Siena and the sweet tradition
Siena has a famous baking tradition that dates back to the Middle Ages, when spices travelled along the same trade routes. Three sweets are the most famous:
- Panforte, a dense, chewy cake of nuts, candied fruit and spices.
- Ricciarelli, soft almond biscuits dusted with icing sugar.
- Cavallucci, spiced biscuits made with nuts and candied fruit.
They are traditionally eaten around Christmas but sold in Sienese pastry shops all year. Savoury Sienese cooking features pici, thick hand-rolled spaghetti, often served with garlicky tomato sauce or breadcrumbs.
San Gimignano, the town of towers
San Gimignano's towers were symbols of rivalry between families, and each house tried to build higher than its neighbours. Over the centuries many fell or were lowered, but the surviving ones still dominate the skyline from a long way off. The town sits on a hilltop above vineyards that produce Vernaccia, and its piazzas and lanes have changed little in appearance.
The legend of the black rooster
The most famous story of Chianti is about a rooster. According to legend, Florence and Siena, long-time rivals, agreed to settle their border by sending a rider from each city at the first crow of a rooster. The place where the riders met would mark the frontier. Siena chose a white rooster and fed it well. Florence chose a black one and kept it hungry, so it crowed far earlier. The Florentine rider set out first and the two met much closer to Siena, which gave Florence the greater share of Chianti. It is a legend, not a record, but it explains why the black rooster became the symbol of Chianti Classico.
The area also has a real historical administration: the League of Chianti, a military and administrative alliance formed in the Middle Ages under Florentine control. Its territory is the core of what is now Chianti Classico.
Cities, villages and open country
One of the pleasures of this part of Tuscany is the change of scale. Siena is a city of steep lanes and large civic buildings, San Gimignano is a village packed within walls, and the Chianti countryside is open, quiet and wooded. Each calls for a different pace and a different kind of attention. Layers of clothing, comfortable shoes and water are useful throughout, and the contrast between a busy piazza and a quiet vineyard track is a good reminder that Tuscany is mostly countryside.
Across all three, a short reading list of landmarks helps: the Campo and the Duomo in Siena, the Collegiata and the Piazza della Cisterna in San Gimignano, and fortified estates such as Castello di Brolio in Chianti.
Useful information
- Wear comfortable walking shoes, as Siena and San Gimignano are hilly and cobbled.
- Tell the organiser about dietary needs and allergies when you book, particularly for nut allergies, since Sienese sweets are nut-based.
- Carry water and sun protection in summer.
- Pack a light layer for churches and for cooler mornings in the hills.
Know before you go
- Sienese traditional sweets contain nuts, so people with nut allergies should be cautious.
- Plan for a mix of city streets, hill-village lanes and country roads.
Frequently asked questions
▸What is the Via Francigena?
The Via Francigena is a medieval pilgrim route from Canterbury to Rome. It passes through both Siena and San Gimignano and is now a long-distance walking route.
▸What is panforte?
Panforte is a dense Sienese cake made with nuts, candied fruit, honey and spices. It is traditionally associated with Christmas.
▸What are ricciarelli?
Ricciarelli are soft, chewy almond biscuits from Siena, usually dusted with icing sugar.
▸What are pici?
Pici are thick, hand-rolled pasta strands from the Siena area, made with flour and water and served with simple sauces.
▸What is the legend of the black rooster?
The legend says Florence and Siena set their border by racing riders at the crow of a rooster. Florence's hungry black rooster crowed early and won more land, which is why it became the symbol of Chianti.
▸What was the League of Chianti?
The League of Chianti was a medieval alliance of communities in the Chianti area, organised under Florentine control for defence and administration.
▸Why did San Gimignano build towers?
Wealthy families built towers as a display of power and prestige and for defence. The rivalry between families drove them ever higher.
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