The Ultimate Tuscany Tour From Florence: Siena, San Gimignano and Chianti

About Florencetown / Towns of Italy

This tour is operated by local company, Florencetown, which now operates nationwide as Towns of Italy. They takes pride in offering small group and private tours throughout Florence and Tuscany.

Towns of Italy promotes unique and fun new ways to discover the country, such as Vespa tours, hiking trips, cooking classes, wine tastings, pizza & gelato making classes, and more.

This Tuscany tour from Florence takes us to the Tuscan towns of Siena with a local guide, offers free time in San Gimignano (in the late afternoon when most of the crowds have dissipated), and an elegant dinner at an exclusive villa in the countryside.

Our driver and tour guide was a young fellow named Giacomo. We hopped into his mini-van and he expertly navigated out of the hectic Florence city center.

Before long, the crowds had disappeared and we were driving down a highway with views of green, rolling hills dotted with tall trees. Giacomo was quite enthusiastic, friendly, and spoke perfect English.

Tuscany Tour From Florence Stop #1: Siena

We received a fully guided tour throughout Siena from a local who has lived in the town for her entire life. It was really fascinating to learn about Siena's rich history and her wealth of stories steeped in tradition.

We also listened to the perspectives of a local citizen who could interject some of her own personal tales.

The historic centre of Siena has been declared a UNESCO World Heritage Site as an exceptional medieval city with a preserved Gothic appearance from the 12th to 15th century. Our guide walked around Siena with us for around two hours, showing us all of the best spots in town.

We were able to ask her any questions as we thought of them. Justin and I thoroughly enjoyed being guided by a local.

We would have never learned as much as we did if we had merely walked around by ourselves. It was a truly enriching experience.

Brief History of Siena

Siena was founded in the time of the Etruscans, and the first documentation mentioning the town dates back to 70 AD. Nowadays, Siena is a smaller Tuscan town, though it used to be a major city centre in the region.

It was located along a major trade route and thrived as a prosperous trading post. The Republic of Siena was an incredible wealthy and highly populated state throughout the Middle Ages.

Unfortunately, the Black Death of 1348 ravaged the city, killing many of its citizens. The Republic of Siena existed for over 400 years until it was defeated by Florence in the Italian War of 1551-1559.

The first place we visited was the Basilica of San Domenico, also known as Basilica Cateriniana.

This church is one of the most important ones in Siena as it is devoted to St. Catherine of Siena. It was first constructed in 1226-1265 and was enlarged in the 14th century.

Over the years, parts of the church have been destroyed by fire, military occupation, and even an earthquake. Unfortunately, I was not allowed to take pictures inside of the church, though it was quite magnificent to see.

There are several large paintings that paid tribute to St. Catherine, displaying stories from her life and after her death when the Pope made her a Saint. The church contains several relics of St. Catherine.

At the Chapel of St. Catherine, there is an altar prominently displaying these relics: her preserved head and thumb.

We left the church and began to walk around the town. One of the first important places we stopped at was Piazza Salimbeni.

Palazzo Salimbeni is a Gothic urban palace built in 1472, located in Piazza Salimbeni. It was associated with the ancient mercantile family, Salimbeni. It now serves as the headquarters for the Monte dei Paschi di Siena, the major banking corporation in Europe.

As our guide explained to us, there were two feuding wealthy and notable families that lived in Siena during the Middle Ages: the Salimbeni family and the Tolomei family. We also saw Palazzo Tolomei (pictured above).

Contrade of Siena

Siena is divided up into 17 neighborhoods, or contrade. Our tour guide had lived in Siena for her entire life and was born in the Nicchio contrada (Seashell district).

Each contrada has its own motto, flag, museum, and fountain. When a baby is born, it is baptized into the contrada which represents that he or she will always belong there.

Each contrada has its own festival week. While we were in Siena, the Oca (Goose) contrada was celebrating. There were lights, decorations, and flags out for the Goose neighborhood.

Twice a year, the 17 neighborhoods compete in the Palio di Siena. This horse race is on July 2nd and August 16th of each year.

In each race, only 10 neighborhoods compete: the seven which did not compete in the previous year, and three by random draw.

The Palio event is much more than just a horse race; it represents the competition and historical rivalries between the contrade.

Piazza del Campo

This interesting shell-shaped piazza is home to the semi-annual Palio races. The jockeys in the race must ride around Piazza del Campo three times, which is covered in a thick layer of dirt.

The event usually lasts about 90 seconds in total. Many jockeys are thrown off the horses during the race, and it is common for a horse to finish a race without its jockey.

The first horse across the finish line is the winner, and that contrada gains all of the glory. The Piazza del Campo also contains the Torre del Mangia, one of the tallest secular towers in medieval Italy.

The tower is exactly the same height as the Siena Cathedral to demonstrate that the church and state are equal in power.

Siena Cathedral

The Siena Cathedral is a very impressive structure with ornate detail carved in marble throughout the facade. It was designed and built between 1215 and 1263. The population of Siena in the Middle Ages exceeded 50,000 people and the construction of a massive addition began in 1339 to accommodate all of the citizens.

In 1348, the Black Plague was devastating to Siena and wiped out about 75% of the city's population. Construction of the addition came to a grinding halt.

The work never resumed as the church no longer required the additional space. The outer walls of the extension can still be seen today.

An interesting fact that I didn't realize until our tour guide explained it: you might see some holes in the walls of some buildings. This demonstrates that the buildings were constructed during the Middle Ages as scaffolding was inserted into these spaces in the walls, and they were never filled in afterwards.

There are an immense amount of structures throughout Siena with these spaces in the walls, which illustrates the ancient age of the town and how it is incredibly well preserved.

Here are some photos from other places in Siena that we discovered on our guided walking tour.

Tuscany Tour From Florence Stop #2: San Gimignano

After exploring Siena, we met with Giacomo who drove us to the next Tuscan town, San Gimignano. San Gimignano is most known for its preserved towers that line the hillside, numbering a dozen or so, creating a medieval skyline.

The historic centre of San Gimignano is a UNESCO World Heritage Site. We arrived in San Gimignano just before 5:00pm, which was perfect timing.

Many of the large tour groups had left for the day, and the busy town was left without very many tourists. Florencetown has designed the tour with the crowds of tourists in mind and tries to minimize our exposure to them. We were very grateful for that!

Giacomo gave us one hour to explore the town, which was a good amount of time. Though it would have been nice to have been guided around the town by a local, it was also refreshing to have a bit of a break.

We were dropped off just outside the city's wall, left to admire the gorgeous pastoral landscape.

Wandering Around San Gimignano

We roamed around at our own pace, discovering the beautiful wonders of San Gimignano. The high walls, tall buildings, and narrow streets kept most of the Tuscan town shrouded in shadows, with rays of sunlight gleaming through at every turn.

Though we were surrounded by cobblestone roads and rocky walls, vines had reclaimed portions of the buildings and potted plants were carefully placed in doorways and alleyways.

We strolled around town, visiting small shops and piazzas, with our necks craned up to admire the tall towers and majestic churches.

Tuscany Tour From Florence Stop #3: Chianti

"See that building up there?" Giacomo pointed towards the side of a huge hill as we drove along. "We will be having dinner at that mansion."

Mansion? As if I didn't already feel spoiled enough by the riches of Siena and San Gimignano, we drove towards an elegant villa nestled in the hilltop of the Chianti region.

Florencetown rents space at a huge mansion in the countryside for their cooking classes, wine tastings, and dinners.

Before dinner, Giacomo told us all about the surrounding vineyards. This region is the ideal climate for growing grapes for wine and olives for making olive oil. There were vineyards and trees growing as far as I could see.

The wine we would be tasting was grown and produced at an estate within steps of the villa, Ruffino Winery. The sun began to set and the sky darkened.

Wine Tasting at Ruffino Winery

There was a separate room for the wine tasting, though we only tasted one wine there. The other wines we enjoyed with our dinner (we tried three different Ruffino red wines in total).

The barrel room was decorated purely for show, though I really enjoyed the ambiance. And we really enjoyed the wine! 

Dinner in Chianti at Ruffino Winery

It was time for dinner! We really didn't expect to be this spoiled.

The chefs created a huge table full of delightful vegan dishes for us! We mentioned that we were vegan and were told that they could create some salads for us. That sounded good to me.

When we walked out to the table, there was dish after dish of delicious Italian meals, and only for the two of us. We were the only two taking this tour, and we had the entire table of food to ourselves.

It was incredible as there were all sorts of local delicacies, highlighting the fresh produce of the region.

There was toasted bruschetta bread with an assortment of different balsamic vinegars and oils to try. There was a bean salad, a chickpea and rosemary salad, pasta in olive oil with fresh herbs, green beans, corn, carrots, grilled vegetables, an eggplant dish, rice dishes, and so much more.

I ate as much as I possibly could, trying a little bit of everything. It was like living inside a dream: talented chefs had prepared fresh and tasty Italian vegan meals for us in a serene and beautiful environment. I even saw a cat through one of the windows!

Though the meal for this tour wouldn't be typically served as a vegan one, it shows that you can definitely make special requests for dietary restrictions or choices. We were so impressed with our dinner.

Booking This Day Tour of Tuscany

We were so impressed with this tour. What a fabulous day we had enjoying Tuscany! At the end of the tour, GIacomo drove us right up to our apartment and dropped us off there to ensure that we didn't have to walk home in the dark.

We highly recommend booking this Tuscany tour from Florence. We could have visited Siena and San Gimignano on our own, but we definitely would not have had as amazing an experience as we did on this tour.

On this tour, we were transported from place to place with ease with the help of our driver. In Siena, we were given a thorough history lesson from our knowledgeable guide that was so interesting.

Otherwise, I would not have learned about the rich background and heritage of Siena. We definitely would not have dined in such a stunning and extravagant setting, and we would not have tried such a wide assortment of local dishes.

More Blog Posts About Tuscany

Looking for more articles about Tuscany? Check out all of our Italy travel guides or browse these recommended posts:

• From Florence to Pisa on a Half Day Trip
• Visiting the Duomo in Florence
• Vegan Guide to Florence
• How to See Michaelangelo's David
• La Farina Apartments in Florence: Where to Stay