Day 2 – San Gimignano and Monteriggioni

Published by

John K

on

October 10, 2025

After a leisurely continental breakfast at Castel Pietraio, we headed north for about 30 minutes to San Gimignano. This medieval walled town is known for its towers, 14 still remaining towers built as a sign of wealth. I believe there were as many as 28 built, the most of any town. Although you could see the town as approaching by car, there were no shoulders on the roads here, and we didn’t encounter any pull-offs with a view to capture any pictures of the town. So here’s a stock photo.

San Gimignano

Parking lot 1 was already full, but we found spaces in parking lot 4 around the other side of town outside the city walls. From there we walked up steps and sloped pathways to enter inside the city walls. As you would expect, narrow streets, piazzas and lots of shops and restaurants.

We perused the shops, and checked out inside the Church of San Agostino, it’s convent and adjoining central landscaped plaza. We stopped at Gelateria Dondali for “the world’s most famous Gelato.”

The famous towers, which really don’t serve much purpose except for viewing are hard to appreciate right in the city. They are more visible from outside the city. Our plan was to stop by a winery just a couple of kilometers outside of town to look back at the city while tasting wine, but Corbucci Wine tasting had closed the nearby location and was now located much further away.

We grabbed a nice lunch (most of us had pizza) at one of the restaurants in the main piazza, explored some side streets and shops. Laura purchased a olive oil dispenser the shape of a pitcher with matching dipping bowls. And we brought a couple of watercolor paintings ( small enough to fit in our suitcase) from an artist shop. He even signed the back of them for us! We found an amazing chocolate shop where we had to get some of the candies we sampled. Then we returned back to Castel Pietraio for another wine happy hour outside on the terrace.

Based on the Julia’s recommendation, our dinner was in the town of Monteriggioni, only 15 minutes away. Osteria Antico Travaglio is within the walls of the small town, perched onto the top of a hill, as are most towns. Approaching the town at night is amazing, as its is all light up around the outside wall.

The dinner was amazing. We all started with our Primi first course of pasta. I had Pici with a cheese sauce topped with pepper. Laura had Lasagna. For our Seconi we ordered family style two Florentine Steaks and three shared side plates of potatoes, spinach, fried mushrooms. The steaks were 1200 grams (~42 ounces) T-Bones, about 2-inches thick. For those that didn’t want their steak rare, their pieces were cooked further.