Siena

What you gain

• ↑Piazza del Campo is the finest medieval public square in Europe: the scallop-shaped piazza, the 102-metre Torre del Mangia, and the Fonte Gaia fountain create an architectural ensemble of extraordinary coherence — sitting in the piazza with a coffee at dawn before the tourists arrive is one of the finest simple experiences in Italy
• ↑Il Palio (July 2 and August 16) is the oldest continuously running horse race in the world and the most intense civic event in Italy: the 90-second race around the Campo, preceded by days of contrada (neighbourhood) rivalry, medieval pageantry, and horse blessing in churches, is genuinely unlike any other event in Europe — book a year in advance
• ↑Siena's Duomo contains the finest medieval carved pulpit in existence (Nicola Pisano, 1268), one of the largest intact medieval floor mosaics (56 scenes in marble inlay), and Pinturicchio's Piccolomini Library — a 45-minute interior visit delivers more concentrated medieval art than most galleries

What you sacrifice

• ↓Getting to Siena from Florence by public transport requires a bus (1.5 hours) — there is no direct train, and the SITA bus system, while frequent, makes day-tripping from Florence more complicated than it should be
• ↓Siena's medieval hill city geography means that the car parks are at the base and the centre is reached by foot or escalator: arriving with heavy luggage requires planning