Poggibonsi, Tuscany
CreatorJaap van Wijngaarden
DateMay 6, 2026
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Day 1
- Start with a slow morning in San Gimignano; go early for the best light and fewer crowds.
- Keep lunch simple in town, then continue to Monteriggioni for an easy walk around the walled village and countryside views.
- Return to Poggibonsi for a relaxed dinner at Ristorante Alcide.
- Pace for the day: classic hill towns, lots of strolling, no need to over-schedule.
Day 2
- Spend the morning in Colle di Val d'Elsa, which feels more local and less busy than the headline Tuscan towns.
- Head into Siena in the afternoon and make time to linger around Centro Storico di Siena - World Heritage Site.
- Keep the evening open for aperitivo and dinner in Siena before driving back.
- Pace for the day: one smaller town plus one major city highlight.
Day 3
- Make this your wine-and-food day with a late-morning tasting at Foresteria Villa Cerna Famiglia Cecchi.
- If you want a second stop, continue to Casale dello Sparviero for a more countryside-focused tasting and lunch pairing.
- Back in Poggibonsi, finish with dinner and a final glass at Innocenti Wines - Ristorante enoteca Poggibonsi.
- Pace for the day: easy driving, long lunch, and no rush in the evening.
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