Walking into Siena feels like stepping back into the Middle Ages. This beautifully preserved hilltop city in Tuscany, a UNESCO World Heritage Site, has kept its medieval character, with brick-red buildings, winding lanes and a warm, intimate feel that's quite different from nearby Florence.

At the heart of the city is the Piazza del Campo, a sweeping, shell-shaped square that's one of the most beautiful in Europe. Twice a year, in July and August, it hosts the Palio, a thrilling bareback horse race between the city's neighborhoods that dates back centuries, along with fierce local pride and pageantry. Climb the Torre del Mangia for spectacular views over the rooftops and the Tuscan hills, and visit the Siena Cathedral, with its striking black-and-white striped marble and incredible inlaid marble floors. Explore the city's museums, enjoy local specialties like panforte and pici pasta, and taste Chianti and Brunello wines from the surrounding countryside.

Siena is about an hour from Florence and makes a perfect base for exploring Chianti, San Gimignano and Montalcino. I'll plan your stay, Palio tickets if your dates line up and Tuscan wine country day trips.