The stage from Casciana Terme to San Gimignano is without a doubt one of my favorites on our self-guided tour. The scenery along this route is simply breathtaking and unforgettable. Surrounded by vineyards and gentle hills, we experience the true essence of Italian living. After several climbs, we take a well-deserved break to enjoy a glass of Aperol Spritz and a delicious plate of pasta. Unfortunately, we spot dark, heavy clouds gathering outside the restaurant, and our ride to the next hotel, Albergo Le Colline, ends up being a rainy one. But as the saying goes—there’s no such thing as bad weather, only the wrong clothing.
Our next stage to Siena is packed with unforgettable highlights. It begins with a stop in the fairytale village of Monteriggioni, which we explore on the recommendation of the friendly staff at our hotel in San Gimignano. We continue through the charming wine town of Castellina before arriving at our destination: the enchanting and vibrant city of Siena. Completely captivated by its timeless beauty, we check in at Hotel Italia Spa in the late afternoon and soon head out for a stroll through the city—a walk that will stay with us forever. Narrow alleyways and quaint shops guide us to our dinner spot, where we wrap up the day with a delicious meal and a warm dose of Italian hospitality.