September to October

Tuscany's cosiest hill-town circuit

Siena, San Gimignano and Montepulciano in shoulder season, a slow loop through the towns rather than a day-trip rush from Florence.

The route

#1
Siena
2 nights
Anchor on Siena. It has the deepest choice of characterful stays and it is the natural hub for the loop, so two nights here lets the other two towns be short drives out and back. Stay near the Campo and the historic centre is car-free at your door.
Where to stay
- 7.8
  Follonico
  Siena, Italy
- 7.3
  B&B Selvabella in Chianti,
  Siena, Italy
- 7.2
  Albergo Il Rondo
  Siena, Italy
#2
San Gimignano
1 nights
San Gimignano is under an hour from Siena and empties out in the evening once the buses leave. That is exactly why you sleep here for a night: the towers and the piazzas are yours after five, and a countryside stay just outside the walls is often cosier than anything inside them.
Where to stay
- 7.1
  Fattoria San Donato
  San Gimignano, Italy
- 7.1
  Agriturismo Poggiacolle
  San Gimignano, Italy
- 7.0
  Casa del Colombaio
  San Gimignano, Italy
#3
Montepulciano
1 nights
End in Montepulciano, the highest and quietest of the three, a steep walkable town of wine cellars and long views. It is the furthest point of the loop, so finishing here means you are pointed back towards the A1 and Rome or Florence the next morning.
Where to stay
- 7.3
  Fonte Martino Guest House & Estate
  Montepulciano, Italy
- 6.8
  Agriturismo Casagrande
  Montepulciano, Italy
- 6.7
  Borgo Tre Rose
  Montepulciano, Italy

When to go

September and October are the sweet spot: harvest light, warm days, cool evenings that make a fire or a heavy door worth it, and the summer crowds gone. July and August are hot and busy. Winter is beautiful but many countryside stays close.