Best Activities in Siena

Venture just outside the city walls to cycle through one of Tuscany's most surreal and beautiful landscapes. The Crete Senesi is characterized by rolling clay hills, stark ravines, and isolated farmhouses sitting atop cypress-lined drives. The roads are often quiet and provide sweeping, unobstructed views of the countryside. It offers a physically rewarding challenge with scenery that looks straight out of a Renaissance painting.

Follow in the footsteps of medieval pilgrims by hiking a segment of the ancient route that connects Canterbury to Rome. The stretches leading in and out of the city are particularly scenic, passing through dense woodlands, vineyards, and ancient fortified hamlets. Walking this historical path allows you to approach the city gates exactly as travellers have done for over a millennium. It is a peaceful, reflective way to experience the surrounding natural beauty.

Given the city's obsession with horses, exploring the nearby woodland trails on horseback feels entirely appropriate. Local equestrian centres offer guided rides through the oak forests and vine-covered hills of the Chianti region just to the north. Suitable for various skill levels, it allows you to access rugged paths and hidden clearings unreachable by car. It is an immersive, tranquil way to connect with the agricultural heartland of Tuscany.

Launch into the early morning sky to witness the sunrise illuminating the iconic patchwork fields and medieval towers below. Floating silently over the Chianti vineyards and ancient hilltop fortresses offers an unparalleled perspective of the region. The flight usually concludes with a traditional prosecco breakfast upon landing. It is a serene, once-in-a-lifetime adventure for those looking to see the landscape from above.