While in Tuscany, it is simple to become oblivious to the stunning splendor of the region’s major cities. When everything is said and done, there are a great number of them in a pretty limited region, and each one requires a visit that lasts for a good several consecutive hours. Nevertheless, if you find yourself with a little bit extra time, or if you get onto a trip that takes you from Florence to Siena, you could have the chance to see one or two of the smaller cities that are every bit as gorgeous as Florence. There are a number of breathtaking villages that can be found along the Chiantigiana road, which is the route that leads from Florence to Siena. Each of these towns is well of a visit, and the terrain is breathtaking. In the Val di Pesa, near San Casciano Although it is just 15 kilometers away from Florence, this hilltop hamlet is a beautiful destination that is sometimes overlooked. It is a beautiful place to get a cup of coffee in the morning since it is surrounded by magnificent cathedrals and fortifications. It is possible to see the Pieve of Santa Cecilia, the Pieve of San Pancrazio, and the Pieve of Santo Stefano if you have an hour of free time before your scheduled appointment. There are many well-known castles in the vicinity, such as Bibbione, Gabbiano, Pergolato, and Montefiridolfi. Additionally, in close proximity to San Casciano lies the hamlet that served as the exile location for Niccolò Machiavelli, an Italian writer and politician. He authored “The Prince and the Mandrake” when he was living in exile while he was in prison. Certaldo An area that is rich in history is Certaldo, which is located a little farther away from the capital of Tuscany. As the place where Giovanni Boccaccio, the author of The Decameron, was born and raised, the most popular tourist destination in Certaldo is the author’s old residence. Palazzo Pretorio or Vicariale, which was originally owned by the Florentine ruling magistrates, is the edifice that represents the highest point in this area. It was first constructed in the eleventh century, but it was reconstructed three hundred years later. If you happen to be in this area during the summer, you may be able to attend the Mercantia festival. This is a spectacular extravaganza that features a variety of performances, including music, magic, theater, and dance. The town of San Gimignano The charming hilltop village of San Gimignano is a more well-known stopover, and it is defined by the fourteen stone towers that date back to the middle ages. One of the most impressive examples of Romanesque and Gothic architecture may be seen in the center of the city, which has been declared as a UNESCO World Heritage site. In addition to that, it is famous for the Vernaccia di San Gimignano wine that it produces, and a trip to the Wine Experience museum is certain to be a pleasure! Fortress of Val d’Elsa Colle Val d’Elsa has a rich and intriguing history, and it is most known for the crystal glassware that it manufactures because of its worldwide reputation. Located in the oldest portion of the town, which is referred to as “Colle Alta,” the Palazzo del Campana, the Castello, the Duomo, and the Palazzo dei Priori are all examples of medieval architecture. The streets are dotted with artisan workshops and craft stores, and if you are interested in purchasing any of the crystal that is created locally, there are an infinite number of choices available to you. Monteriggioni Along the Tuscan portion of the Via Francigena, Monteriggioni was a historically important stopover. It was a lovely walled town that was placed high on a hill. Even though the walls are just as intimidating as they have always been, once you go inside this beautiful venue, you will find that it is just as hospitable as any other establishment in the area. On a yearly basis, this location plays host to both the Monteriggioni Medieval Festival and the Slow Travel Fest. During the process of organizing your journey from Florence to Siena, I hope that you will be persuaded to make a few of stops along the way. There is a high probability that the majority of organized excursions will offer the opportunity to visit at least one of these towns. It is important to keep in mind that when you book an organized trip, it is ideal to collaborate with a local operator that has a good reputation. Publisher’s Plate Mauro Bramante is the Director of WalkAbout Florence, an independent company that provides tours and excursions around Italy that are really remarkable. These tours and excursions include day trips from Florence to Siena. It doesn’t matter whether you want to ride a vintage Vespa, sample the world-famous Chianti wine, or get your hands dirty in the kitchen with fresh foods from the area; Mauro’s business guarantees exhilaration, adventure, and most importantly, fun. There is no need to seek any farther than WalkAbout Florence for your next vacation if you are eager to experience the enchantment of Italy with the assistance of some tour guides who are enthusiastic and very informed.