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Tuscany

Florence, Siena & the Val d'Orcia

Tuscany

FOOD7 days

Renaissance cities and hill towns, with the Val d'Orcia in between

Dosage

7 days

Indication

Art, wine, food & landscape

Contra-indication

August heat and crowds

Side effects

A cellar full of Sangiovese

Florence, Siena & the Val d'Orcia  why go

A week of Tuscany that balances the cities against the countryside. Start with Florence and its art, wind through the hill towns of Montepulciano and Siena, and give yourself real time in the Val d'Orcia — the rolling, cypress-lined landscape everyone pictures when they think of Italy.

✦  Walked in person. Every stop below is from our own notebook — including the wrong turns.

2 min readShare

At a glance

Dosage7 days

The itinerary  what to do, where

4 places

The route

F

Florence

The cradle of the Renaissance, best taken slowly. Book the big galleries ahead, then leave time to just wander the Oltrarno side of the river.

What to do

  1. 01The Duomo and Brunelleschi's dome — book the climb
  2. 02Uffizi and Accademia galleries (timed tickets, well ahead)
  3. 03Ponte Vecchio and the Oltrarno artisan workshops
  4. 04Sunset from Piazzale Michelangelo

Eata proper bistecca alla fiorentina; coffee in Santo Spirito

Florence
Florence
TipReserve the Uffizi and the dome climb online days in advance — the on-the-day queues cost you half a morning.
M

Montepulciano

Up into the hills and the wine. A Renaissance town stacked on a ridge, famous for its Vino Nobile and the cellars carved beneath the streets.

Stay: an agriturismo in the surrounding countryside

What to do

  1. 01Walk up to Piazza Grande at the top of the town
  2. 02A Vino Nobile tasting in an underground cellar
  3. 03Day trip to nearby Pienza for pecorino cheese
Montepulciano
Montepulciano
TipBase yourself at a rural agriturismo here rather than in town — it's the best way to feel the Val d'Orcia.
S

Siena

Medieval to Florence's Renaissance. The great shell-shaped piazza, a striped cathedral, and streets built for walking, not cars.

What to do

  1. 01Piazza del Campo and the Torre del Mangia climb
  2. 02Siena Cathedral and its marble floor
  3. 03Get lost in the contrade — the old city districts

Eatpici pasta and a glass of Chianti

Siena
Siena
TipThe Campo is the place to sit with a coffee and watch the town — arrive before the tour buses at mid-morning.
V

Val d'Orcia

The postcard landscape and a slow last day. Rolling hills, lone cypress trees, and the thermal town of Bagno Vignoni before you head home.

Getting there: fly out of Florence or Rome

What to do

  1. 01The classic drive between San Quirico d'Orcia and Pienza
  2. 02The cypress-lined roads near San Quirico — the photo everyone wants
  3. 03A soak at the thermal baths of Bagno Vignoni
Val d'Orcia
Val d'Orcia
TipGolden hour is everything here — plan the Val d'Orcia drive for the last hour of light.

From the road  8 photographs

Before you go  take it with you

Make Tuscany your next story

Questions about timings, seasons, or where to swap a stop? Write to us — we answer every message with the map open.

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Read the route
IndicationArt, wine, food & landscape
Contra-indicationAugust heat and crowds
Side effectsA cellar full of Sangiovese