
Siena in the morning: the Piazza del Campo, tilted like a shell and home to the Palio, and the striped marble cathedral, whose entire floor is a storybook. In the afternoon, San Gimignano, forty minutes away, which keeps fourteen of its seventy-two medieval towers. Arriving late at San Gimignano is the best part: the coaches leave at five.
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A suggestion, not a rule: once you create the trip you can split it up however you like.
4 min on foot hasta la siguiente
28 km · by transport hasta la siguiente
💡Turn up at three and you do not eat
Tuscan kitchens serve from one to half past two and from half past seven to ten, and outside that they really do close, especially in small towns. The places on tourist squares that serve at any hour are exactly the ones to avoid. And many trattorias close one full day a week, usually Monday or Tuesday.
💡Three things to book ahead: the Pisa tower, the Siena floor and the wineries
Climbing the tower in Pisa needs a timed ticket and sells out in season. The cathedral floor in Siena is only uncovered for a few weeks a year, so check the dates before counting on it. And the wineries in Chianti and Montepulciano receive by appointment, not by walking in: write to them a few days ahead.
💡The Val d'Orcia is a first-and-last-light place, not a midday one
At midday the sun falls flat and the hills look washed out. What appears in the photographs — mist in the valleys, cypresses cut out against the sky, long shadows — happens at dawn and in the hour before sunset. If you only have one slot, take the end of the day, when the viewpoint car parks are empty too.
💡Do not drive into historic centres: the fine arrives months later
Nearly every Tuscan town has a ZTL, a limited traffic zone, marked with a red circle and watched by cameras. Nobody stops you: the fine reaches you at home months later, and with a hire car the company adds its own admin charge. Park outside and walk in, which is short everywhere. If your hotel is inside, ask them to register your plate before you arrive.
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