Late spring (May and June) and early autumn (September and October) are ideal, with warm days, cooler evenings, and the Tuscan countryside at its greenest or its golden-harvest best. Summer is hot and busy, but it is also Palio season: the two horse races run on July 2 and August 16, drawing huge crowds and a electric atmosphere (book accommodation months ahead if you want to be there). July and August afternoons can top 32C/90F. Winter is quiet, cool, and atmospheric, with lower prices and misty vineyards, though some rural wineries and restaurants keep reduced hours.

Siena has no major airport of its own; most visitors fly into Florence (Amerigo Vespucci, about 75 minutes by car) or Pisa (about 90 minutes), then take a bus or train. The fastest public option is the direct Autolinee Toscane rapida coach from Florence (roughly 75-90 minutes), which drops you near the center; trains are slower and the station sits downhill from the old town, connected by escalators and buses. Once inside the walls, Siena is entirely walkable and largely pedestrianized, so wear good shoes for the hills and cobbles. Driving into the historic center is restricted by a ZTL zone with camera fines, so park in a garage like Santa Caterina or Il Campo and continue on foot.