The red glow cast by the setting sun illuminates the tuscan hills with a magenta glow, blushing in a way I have not yet seen before. The marbled, snow-white peaks of mountains burn red to match the sparse clouds that float above on this clear winter day. I spend nearly an hour on top of this fortress, watching the sunset over the UNESCO world heritage valley.

San Gimignano is one of the most charming medieval towns I have had the pleasure to visit this year. Heavily restored at the beginning of the 20th century in honor of the 600th death-day of Dante Alighieri, who visited the city as a diplomat and drew inspiration for his Divine Comedy. Now 700 years later, the buildings maintain a medieval look mixed with modern paved roads, making much of the winding alleys and steep side streets accessible.

Entering through the front gate of San Giovanni, I am transported back to the 13th century, when the gate was first built. Aromas of wood burning fill the air, mixing with the butcher and cheese shops lining the Main Street. Following it to the central plaza, I find large towers and an interesting arch monument by the town hall.

I wind my way through the outskirts of the town, embracing a beautiful tuscan vista with mountains as the backdrop. I walk nearly the entire way along the outer wall “passagiata di Mura”, deviating only to walk through a park towards a medieval fountain.

I return to the town center through a church complex and trace the cobblestone streets to the main road. I hike my way up to the fortress only to discover I have seen nearly the whole town, in under two hours!

With little else to do, I head down the greenery of the fortress towards the huge tower. There is a museum of christian art, in the byzantine style which I much prefer for its use of gold and sometimes humorous depictions of common folk. I scale up, up and up through the almost rickety grand tower, up 50 meters to the top with a dangerous, but beautiful 360 degree view of the valley. I see all the iconic landmarks from here, and realize there is one more street to visit!

I go down and make my way through the last of the main streets, ducking into what seems like every last medieval archway and alley tunnel, until I find myself on the outskirts of the town walls again. I snack on some ripe wild strawberries (unrelated to strawberries, but delicious all the same) until I return to the fortress for the sunset.

After enjoying the sunset display, I watch the town illuminate with Christmas lights as I make my way back in time for the bus. I dine on a delicious carbonara crepe, which would ordinarily horrify French and Italians alike, but I quite enjoy. The main plaza is aglow, and the large town is lit up in purple, an interesting choice, and I make a final tour through the main streets as I bid arriverderci to one of my new favorite Tuscan towns.

A layover between buses allows me some time to explore Poggibosi, which was once a central hub of Tuscany. There are a couple blocks with lights strung up, so I kill time and am surprised to see many medieval palaces of Medici and others lining the streets.