Horseback Riding in Chianti with Under The Tuscan Sun Tours

Set in the heart of Tuscany, just a short drive from Florence, Under The Tuscan Sun Tours guides riders through the Chianti region’s rolling vineyards, olive groves, and medieval villages on horseback. This area offers a distinct blend of natural beauty and cultural depth, far from the bustling streets of the nearby cities. Riding here is a chance to absorb Tuscany’s famed rural landscape in a quiet, deliberate way, where every turn reveals terracotta rooftops, cypress-lined lanes, and softly undulating hills carved from limestone-rich soil.

The trip covers historic towns like Siena, San Gimignano, and Monteriggioni, each a living postcard of Tuscan architecture and heritage. San Gimignano’s towers looming in the distance, Monteriggioni’s perfectly preserved walls, and Siena’s ancient streets provide a fascinating narrative backdrop that enriches the ride. These towns hold centuries of history, from Etruscan origins to medieval defenses, which echo subtly in the peaceful countryside.

What sets Under The Tuscan Sun Tours apart is their knowledgeable guides, local to the area, who navigate these landscapes with skill and passion. Their focus on small groups ensures a personalized experience, whether you’re an experienced rider or new to horseback travel. The horses are calm and accustomed to the terrain, making this adventure accessible and safe.

Riding here means encountering unique Tuscan native flora such as umbrella pines and fragrant scrubland herbs, while the open landscapes invite wide views under expansive skies. It’s a practical way to connect with the environment on foot’s slower cousin, carving out space to appreciate the region’s distinct feel—bucolic yet historical, wild yet cultivated.

For travelers visiting Florence and seeking a distinct outdoor experience beyond the city’s art and architecture, this horseback journey offers an active, immersive route to Tuscany’s heart. It balances physical activity with cultural insight, connecting horse, rider, and landscape in a way that’s simultaneously timeless and thoroughly present.