What Awaits You

Escape the ordinary and step into a living medieval canvas where time seems suspended among rolling hills, ancient towers, and vibrant piazzas. Your private driver navigates Tuscany’s picturesque landscape while sharing insider knowledge about the region’s rich tapestry of history and culture.

In magnificent Siena, a private art historian reveals the stories behind the fan-shaped Piazza del Campo—stage for the legendary Palio horse race—and the dramatic zebra-striped cathedral. Wander through narrow medieval streets where centuries-old rivalries between noble families shaped this UNESCO treasure into the architectural gem it remains today.

Journey deeper into the Chianti countryside to an organic family vineyard where tradition meets terroir. Tour sun-drenched vineyards and cool cellars before savoring a farm-to-table lunch paired with estate wines, guided by experts who illuminate the secrets behind Tuscany’s liquid gold.

The adventure culminates in San Gimignano, the “Medieval Manhattan,” where stone towers pierce the sky—silent sentinels from an age of ambition and artistry. Explore cobbled lanes at your own pace, discovering artisan shops and breathtaking vistas that capture the essence of Tuscany’s timeless allure.

Signature Experience
This extraordinary adventure is exclusively available as a part of a personalized Nancy Aiello Tours itinerary.