San Gimignano, Siena & Chianti Tour

Enjoy a full-day tour of Tuscany’s villages and wine regions from Florence and travel into the heart of the beautiful Tuscan countryside. Visit the town of San Gimignano, the wine territory of Chianti, the medieval town of Siena, and the Monteriggioni.

Enjoy a full-day tour of Tuscany’s most fascinating villages and wine regions. Come with us and travel to the heart of the Tuscan countryside. We’ll take you to visit the town of San Gimignano, the Chianti wine region, the medieval town of Siena, and the well-preserved Monteriggioni castle. Follow us on a journey through space and time!

What you will visit: San Gimignano and Siena Chianti area

The town of San Gimignano relies on the top of a low hill at the center of Valdelsa. This wonderful landscape will seduce you with its unique skyline made of towers. They were built during the 14th century by families who wanted to demonstrate their growing power. At those times, after gaining autonomy from Volterra, more than seventy towers have been built in the S. Gimignano town center. This process was transforming a rural village into a prestigious town.

The tour will continue with the Chianti area and the Medieval town of Siena, both are situated in the heart of Tuscany. All these are compelling stops for those who want to see the true Tuscan landscape. You will learn about the region’s history and traditions. You will taste excellent food and wines. Here you will be able to find some of the most ancient Tuscan wine producers, family-run, still active for centuries. If you are asking yourself what villages are worth the visit, if you are curious to know exactly where is the Chianti region, all your doubts will be satisfied after this tour. When you’ll be there you will forget your problems and start to discover a lost rhythm in life.

How to get to San Gimignano from Florence

Your journey will start in Florence where you’ll meet our kind staff. Please come to the Villa Costanza tram terminal, at the end of Tramway 1, an easy-to-reach location, where you can also leave your car with comfort and ease.

Onboard, after the bus departure, you will be introduced step by step to the places you are going to see and visit. The first stop will take place really soon. After approximately one hour of losing yourself in the magical landscape of the Chianti Fiorentino (Florentine Chianti), you’ll reach San Gimignano. This is an extraordinary example of a well-preserved Medieval urban town, with the original old walls. This is also the main reason why UNESCO included this town in the world heritage sites.

Art, museums, and the best Italian ice cream are here

You will have free time to visit everything you want. The old town center is full of alleys and beautiful squares, museums, palaces, churches, magnificent towers, and craftsmen’s workshops. Furthermore, if you are interested in contemporary art, in San Gimignano you will find interesting contemporary art galleries, like the Galleria Continua, hosting works made by some of the most famous and valued international artists.

If you are looking for simpler and more popular things to do in San Gimignano, then you can taste one of the best ice creams in town. Here you can find few world-famous gelaterias, like Il Criollo or Gelateria dell’Olmo.

Chianti wine region: the taste of the Classic area

Your tour continues to the splendid area of the Chianti Classico in the Siena province. This is the original Chianti area. We will stop by a typical Tuscan winery where you will visit the cellars and vineyards. Afterward, you will taste the wine produced.

The magnificent Siena cathedral and the Palio square

In the afternoon the tour continues with sightseeing in Siena. Here our official guides will lead our tour to the old city center. You will have the chance to admire the magnificent Siena Cathedral (called Duomo) and the Town Hall in the Piazza del Campo, the scenery of the world-famous Senese Palio horse race.

Last stop: the Monteriggioni castle, another jewel of Tuscany

The tour will end with the visit to the marvelous Monteriggioni castle, a medieval fortress really well preserved that you may know also for the Assassin's Creed videogame series.

After this stop, it will start your ride back to Florence where the tour will end.