Castello Di Gabbiano  

Set among 100 hectares of olive groves and vineyards in San Casciano in Val di Pesa, in the heart of Chianti Classico. About 14 miles from Florence and within easy reach of Piazzale Michelangelo, Pitti Palace and the Ponte Vecchio. A medieval castle escape not far from Florence and Siena.

Stay in a medieval castle on a working farm with trekking paths through the vines. Rooms echo Tuscan Renaissance style with rustic terracotta floors, wooden furniture and mini‑bars; many feel like intimate country suites. Air conditioning is available in summer and the grounds include a large garden and an outdoor pool.

Outdoor swimming pool, on-site parking and pet-friendly rooms. Daily wine tastings, a chapel, laundry and ironing services, plus trekking routes among the vineyards. Wake up to olive-and-vine-scented mornings on a 100-hectare estate.

Breakfast features Tuscan specialties served in a drawing room or out in the garden. From April through November, lunch and dinner are available Tuesday evening to Sunday evening at a nearby restaurant 230 feet from the castle. Local wines are showcased with daily tastings.