Siena is one of the finest medieval cities in Europe — and one of the most underestimated. While Florence draws the crowds, Siena has kept its character almost entirely intact. The Piazza del Campo, one of the greatest public spaces in the world, still functions as the living heart of the city. The Cathedral — striped black and white marble inside and out — is extraordinary, and the narrow streets of the historic centre, a UNESCO World Heritage Site, are genuinely worth exploring at your own pace.

San Gimignano is just 30 kilometres from Siena — a hilltop town famous for its medieval towers and its exceptional white wine, Vernaccia di San Gimignano. The museums and civic buildings are worth a visit, but the real pleasure here is simply walking the streets, looking out over the Val d'Elsa and stopping for a glass of Vernaccia at one of the enotecas in the main square.

Between the two cities, the route passes through the heart of the Chianti Classico wine region. We include a private tasting stop at Fattoria La Marronaia — a family-run estate in the Chianti hills producing Sangiovese, Merlot and traditional Tuscan blends. The tasting is private and arranged in advance, so your group will not be joining a tour. Just you, the wine and the view.

Your driver collects you from your hotel or address in Florence at whatever time suits you. The route and pace are entirely yours — the itinerary below is our recommendation, but every element can be adjusted to match what you actually want from the day.