SIENA · TUSCANY
Cathedral on the hill, vineyards in every direction.
A working guide to Siena and the Tuscan country around it. Brunello, Chianti, the striped Duomo, San Gimignano, Val d’Orcia — the days actually worth taking, ranked by what travellers said about them.
Only in Siena
Three things you only really get here.
Vineyard tours and cooking classes exist all over Italy. Brunello straight off the slope it grew on does not. The Duomo’s inlaid marble floor does not. Cooking pici in a Sienese home does not. Three days the city actually owns.
In the vineyard
Brunello at the source
Brunello di Montalcino comes from one grape (Sangiovese Grosso) grown on one hill (Montalcino) under one DOCG. Drink it in a cellar in Florence or London and you are paying to ship it out of here. Drink it where it is made and the bottle costs less, the producer poured it, and the view is the slope the grapes came from. Hour and ten by road from Siena.
- 1 Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
- 2 From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch
- 3 A Brunello Cooking Class with Vineyards View Winery
Inside the Duomo
The striped marble & the floor
White and black serpentine stripes climbing the pillars, a marble floor inlaid as fifty-six storytelling panels, Pinturicchio frescoes glowing in the Piccolomini Library next door. The cathedral floor only fully uncovers a couple of months a year. The skip-the-line ticket and the OPA SI Pass both get you in; the trick is knowing which days the panels are open.
- 1 Siena: Siena Cathedral and Piccolomini Library Entry Ticket
- 2 Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
- 3 Siena: Walking Tour and Skip-the-Line Duomo Tickets
In a Sienese kitchen
Pasta with Tuscan hands
Half the cooking classes here are in actual farmhouses outside the walls, half are with home cooks (the Cesarine network and similar) who teach you tagliatelle, pici, ribollita, tiramisu in their own kitchens. Lunch on the terrace afterwards. A Sienese skill set you take home, plus the wine on the table while you cook.
- 1 Tuscan Cooking Class in Central Siena
- 2 Siena: Pasta and Tiramisu Cooking Class with Wine
- 3 Siena: Small group Cooking Class in Chianti Farmhouse
If you only have one day
The Tuscan day everyone books first.
If you can only take one organised day out of Siena, this is the one. Big numbers, repeat bookings, near-perfect ratings — the day trip the rest of your week gets planned around.
The classics
Siena’s Most Popular Days Out
Chianti, Brunello, the Duomo, San Gimignano, the cooking classes. The bookings travellers come back to write five-star reviews about.
By place
Pick a corner of Tuscany.
Siena is the base. Each tile is a day out from it. Chianti for the wine roads. Val d’Orcia for the cypress photo. San Gimignano for the towers. Montalcino for the cellar lunch. Florence if you want a long Uffizi day and a late train back.
By experience
Or pick how you want to spend the day.
Wine cellar in Chianti. Pasta class with a Sienese home cook. Vintage Fiat 500 through the cypress avenues. Truffle hunt with a dog in San Miniato. Pick the shape of the day; the destinations follow.
16 AUG 2026 · Next race
Palio dell’Assunta
Two days a year
The Palio. Ninety seconds. Seventeen contrade.
The Campo gets packed flat with dirt for two afternoons every summer. Bareback riders representing the city’s seventeen contrade race three laps around the medieval shell. The whole thing is over in roughly ninety seconds. The losing contrade carry their hurt for the next twelve months. The winning one parades it.
If you are in Siena around 2 July or 16 August, plan your day around it. If you are not, the contrade museums and the Campo itself are open the rest of the year — and a guided city walk picks up the contrade lines block by block.
Siena city walks →The wine roads
Three glasses of Tuscany.
Chianti for the family castles and the lunch under the cypress. Brunello for the slope and the cellar. Vino Nobile for the cellar staircases under Montepulciano. One day per glass; the highest-rated way into each.
Up another hill
The hilltop village days.
San Gimignano’s towers, Pienza’s pecorino, Volterra’s alabaster, Monteriggioni’s walls, the cypress avenues of Val d’Orcia in between. Three days we’d hand-pick for a first week out of Siena.
Inside the walls
Slow days in Siena.
The Campo, the contrade alleys, the Sienese food, the Fiat 500 tour around the city walls, the secret medieval tunnels under the Duomo. Three city-only experiences that don’t need a rental car.
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