The Campo, and everything past the walls.
The shell-shaped piazza, the black and white Duomo, and the wine roads out to Chianti, Montalcino and San Gimignano. What each tour is really like, what it costs, and where to book.
What to book before anything else.
Second visit or first, these are the ones travellers keep coming back for: a walk through the contrade to the Campo, a long lunch among the Chianti vines, a cellar in Montalcino that pours the real Brunello.
Siena Cathedral and Piccolomini Library Entry Ticket
Skip-the-line entry to Siena Cathedral and the Piccolomini Library. See Duomo mosaics and Pinturicchio frescoes for $9.
From $9 per person
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The wine country starts ten minutes past the gate.
Sangiovese on stony hills, cypress lanes to a family cellar, lunch on a terrace with the whole Orcia valley laid out below. A Tuscan wine day is the outing most people plan the whole trip around, and the one worth choosing carefully.
Which wine road is yours?
Everyone wants a day in the vineyards; the right one depends on your taste and your trip. Three ways to spend it. Pick the one that sounds like you, and every tour behind it is already reviewed and priced.
Closest to home
The Chianti day
from $164 · 3,762 reviews
The hills between Siena and Florence, black rooster on every bottle, castles that have made wine for eight centuries. Easy to reach, generous with the tastings, and the safest first bet if you have never done a Tuscan cellar before.
Compare the Chianti days →
The serious reds
The Brunello day
9 hours (approx.) · from $217 · 952 reviews
South to Montalcino, where Sangiovese Grosso ages for years and lunch happens inside a fortress. Fewer stops, deeper pours, bigger wines. For the traveller who came to Tuscany mostly to drink it properly.
See the Montalcino days →
Towers and a white
The San Gimignano day
2 hours 45 minutes (approx.) · from $108 · 170 reviews
The medieval skyline of towers, plus the one great white in a region of reds: crisp Vernaccia poured within sight of the walls. Half sightseeing, half tasting, and the pick when the group cannot agree on wine alone.
See the San Gimignano days →
The best hours are the slow ones.
Dinner comes late in Tuscany and lasts. A table set in the rows as the hills turn gold, a cellar opened by candlelight, a food walk through Siena that ends over Chianti Riserva. The kind of evening you book once and talk about for years.
Learn to cook it, then eat it.
Pici rolled by hand, ragu left to tick over all morning, pecorino and warm bread to start. A Tuscan kitchen sends you home able to make the meal, and very full before you leave it.
Truffles, oil and pecorino.
A dog and a hunter into the oak woods for truffles, a mill press near Montalcino, a dairy in Pienza where the pecorino is still made by hand. The tastes that never leave the region, met where they are actually made.
Siena keeps its medieval self.
The Campo where the Palio is run, the seventeen contrade with their flags and fountains, the striped Duomo and the frescoed Piccolomini Library. A good guide turns the old stones into the story of a city-state, if you take the right hours.
Siena, and the towns around it.
Southern Tuscany works town by town, each an easy run from a Siena base. Chianti for the classic cellars. Montalcino for the big reds. San Gimignano for the towers. Pienza for the pecorino and the view.
What kind of day do you want?
Twelve ways to spend a day in southern Tuscany. Pick the one that sounds like your kind of afternoon and every tour behind it is already reviewed and priced.
A day out, back by dinner.
The best of southern Tuscany sits within an hour of Siena. Walled hill towns, DOCG cellars, cheese dairies and the cypress roads of the Orcia valley, each an easy morning out and home in time for a proper meal.
The first three days.
You cannot see all of southern Tuscany in one trip; you can absolutely do the right three days from Siena. Do it in this order and nothing feels rushed.
Day 1
Settle into Siena
The Campo first thing, the Duomo and the Piccolomini Library, a slow walk through the contrade, then a food tour that turns into dinner. Easy pace, all on foot.
Start in the Campo →
Day 2
Into Chianti
North into the black-rooster hills: two family cellars, a castle, lunch among the vines. Swap in a Vespa or a Fiat 500 if you would rather drive the roads than ride them.
Into the Chianti hills →
Day 3
South for the Brunello
Down to Montalcino and Montepulciano for the biggest reds and the widest views, with a stop in Pienza for pecorino. The long day, and the one people remember.
South to Montalcino →
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