Traveleriences
Siena's rooftops and Piazza del Campo from above, with the Torre del Mangia

Siena & Chianti, Italy

Ideal: 3 daysBest: Apr–Jun, Sep–OctPrice: Expensive
OverviewSeeEatHidden gemsAreasStayPracticalHistoryNearby

In 60 seconds

Siena & Chianti in 60 seconds

Siena is the Gothic counterpart to Renaissance Florence: a hill city of brick lanes that all run down to Piazza del Campo, the shell-shaped square where the Palio horse race is run twice a summer, on 2 July and 16 August, by riders from the city's rival districts. Climb the Torre del Mangia, then cross to the striped cathedral, whose inlaid marble floor and painted Piccolomini Library are among Italy's great sights. North of the city, between Siena and Florence, lies Chianti Classico — wooded hills, cypress drives, castles that are now wineries and villages such as Castellina, Radda and Panzano, where a butcher recites Dante over the bistecca. South, the Val d'Orcia's rolling fields lead to Pienza and Montalcino. Three days, with a car for the hills.

MedievalWineCountryside

Best for

  • Art
  • History
  • Food

Known for

  • Piazza del Campo
  • The Palio
  • Siena Cathedral
  • Chianti Classico

Skip if

You want to see Tuscany without a car — Siena is fine by bus, but Chianti and the Val d'Orcia really need one.

Your match

Choose a few travel interests and we will show how well Siena & Chianti fits them. Choose interests

See

Must experience

The things that would make the trip incomplete without them.

Piazza del Campo & Torre del Mangia

The shell-shaped square and its tower

Sit on the sloping bricks like everyone else, then climb the town hall's tower for the view over the rooftops.

CentroFreeMust-see

Siena Cathedral

Moderate

Striped marble, inlaid floor and the Piccolomini Library

Black-and-white marble everywhere, a floor of inlaid scenes, and a library painted by Pinturicchio in colours still fresh.

DuomoArtGothic

The Palio

A bareback horse race round the Campo

Ninety seconds of chaos on 2 July and 16 August, after days of pageantry; stand in the centre of the square for free, or book a balcony.

Piazza del CampoSummerTradition

Chianti Classico villages

Castellina, Radda, Gaiole and Panzano

Drive the winding roads between hill villages and castle wineries; taste Chianti Classico where the black rooster is on every label.

ChiantiCountrysideWine

Eat

Where to eat

A short list, kept short on purpose. Each entry answers one question: when is this the right choice?

More places to eat

Too few picks yet for their own heading, so they share this list.

Osteria Le Logge

Expensive

Creative Tuscan cooking in an old pharmacy

Dark wooden shelves of the old pharmacy and modern Tuscan dishes, a few steps from the Campo.

CentroBook aheadTuscan

Antica Osteria da Divo

Expensive

Dining in rooms cut into the rock

Sienese dishes in candlelit cellars carved from the tufa, near the cathedral.

DuomoAtmosphericTuscan

Nannini

Inexpensive

Old Sienese pasticceria

Stand at the bar for coffee and a slice of panforte or a ricciarello, Siena's almond biscuit.

Banchi di SopraCoffeePanforte

Beyond the obvious

Hidden gems

Less obvious, rarely queued for, and usually the part people remember.

Monteriggioni

A walled village crowned with towers

A complete ring of 13th-century walls on a hilltop; walk the ramparts at sunset.

MonteriggioniFreeMedieval

Orientation

Neighbourhoods

How the city is actually divided, and what each part is for.

The contrade

Seventeen rival districts

Each has its own flag, church, fountain and museum; look for the animal emblems on the street corners.

Stay

Where to stay

Areas rather than hotels — pick the right one and the rest follows.

Inside Siena's walls

Expensive

Hotels in the car-free centre

Stay in the city for evenings in the Campo once the day trippers have gone.

EveningsWalkable

Chianti farm stays

Expensive

Agriturismi among the vineyards

A farm with a pool and its own wine is the classic Chianti stay.

Car neededCountryside

Practical

Know before you go

Getting in
Direct buses from Florence take about 75 minutes and drop you nearer the centre than the train.
Getting around
Siena's centre is car-free and steep; for Chianti and the Val d'Orcia, hire a car.
The Palio
Hotels fill months ahead for 2 July and 16 August; the square is packed from early afternoon.
When to go
April to June and September to October; the grape harvest is in late September.
Taste locally
Chianti Classico, Brunello, pici pasta, Pecorino di Pienza, bistecca and panforte.

Plan this trip — useful links

Terre di Siena — official guide (opens in a new tab)

Context

History in 5 minutes

Enough to make what you are looking at legible.

  1. 1287–1355

    The Council of Nine governs Siena's golden age; the Campo and the town hall are built.

  2. 1348

    The Black Death kills much of the population and halts the cathedral's vast enlargement.

  3. 1716

    Grand Duke Cosimo III defines the boundaries of the Chianti wine zone, among the first in the world.

  4. 1995

    Siena's historic centre is inscribed on the UNESCO World Heritage list.

Further out

Nearby escapes

Worth a day if you have one to spare.

Val d'Orcia, Pienza & Montalcino

UNESCO-listed hills, Pecorino and Brunello

The cypress-lined landscape of the postcards, Pienza's Renaissance square and Montalcino's Brunello cellars.

1 hr by carUNESCOWine

San Gimignano

The town of towers

Fourteen surviving medieval towers; come early or late to miss the coaches.

45 min by carMedievalUNESCO