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The Perfect Day Trip From Florence

A few months ago Jason and I had the pleasure of spending a week in Florence. Most of the time we spent exploring that lovely Italian city, but we knew we wanted to get out and explore Tuscany for at least one day.

However, with so many charming towns and villages in Tuscany, it was tough to choose a day trip from Florence, Italy. Fortunately I had recently been introduced to a company called Walks, and found a tour on their website that was perfect--Tuscany Day Trip With San Gimignano, Chianti and Siena. 

Over the course of ten hours we would visit two classic Tuscan towns, drive through miles of beautiful countryside and eat a delicious lunch paired with regional wines. Add in a personable and knowledgeable guide and this turned out to be the ideal Tuscany day trip from Florence.

View of the countryside surrounding San Gimignano
View of the countryside surrounding San Gimignano

San Gimignano

Our first stop on the tour was San Gimignano. Our tour group was among the first to arrive so we had time to explore and appreciate the small village before it became too crowded. Our guide, Nebojosa, gave us some history about San Gimignano and then allowed us time to explore.

There have been settlements on the site of San Gimignano dating back to the 3rd century B.C. The current village began between the 6th and 7th centuries A.D. During the Renaissance this village was a popular resting place for pilgrims on their way to Rome. Today San Gimignano’s city center is recognized as a UNESCO World Heritage site.

Wendy and Jason at San Gimignano
Wendy and Jason in San Gimignano

One of the products for which San Gimignano has long been known for is saffron. In the last  few decades it has been the home of the highly regarded Gelateria Dondoli. Combine those two facts and you have saffron gelato. If you ever get to this tiny village, don’t leave without enjoying this gelato. And don’t mind the lines, the store is well staffed and quite efficient.

Wine barrels
Wine barrels at the Sant'Appiano winery

Lunch And Wine Tasting In Chianti

After our gelato is was time to head to Chianti for lunch and wine tasting. No wonder I love Italy so much! On the day of our tour we visited Sant'Appiano (the winery selected may vary for each tour group). We started with a short introduction to the winery and then were led upstairs for our meal.

Our group sat around a large rectangular table and spent the next hour and a half sipping wine and enjoying a flavorful three course meal. In typical Italian fashion the food was served slowly which allowed plenty of time for conversation with our fellow tour guests. We began with bread, cheese, meats and olive oil. Then a roast pork entree was served. And to make it a perfect Italian meal we ended with tiramisu for dessert. All the food is made on site using only local ingredients. Periodically our winery host would introduce a new wine and discuss its profile. 

If the tour had ended here, we would have been happy, but the best was yet to come.

Tour group enjoying lunch at a winery in Chianti
Our group enjoying lunch at Sant'Appiano Winery in Chianti

Tour of Siena

Many years ago I read a novel that took place in Siena. Unfortunately I can’t remember the name of the book, but it left me with a desire to visit Siena. In fact I had considered just booking a Siena day trip from Florence. Needless to say, I was very eager for this last stop on our tour.

Nebojosa led us on a short walking tour of the city sharing the city’s history along the way. Eventually we arrived in the main square, Piazza del Campo. Here we learned about the famous horse race, Palio di Siena. This adrenaline-fueled race takes place in the piazza, once in July and once in August, while 30,000 spectators watch.

View of Siena
View of Siena
Piazza del Campo in Siena, Italy
Piazza del Campo

Siena was founded as a Roman military outpost in 30 A.D. After the fall of Rome, the city was controlled by a variety of factions including the Catholic church. During much of its history Florence was its chief rival and several wars were fought to gain control. Eventually Florence gained the greater wealth and power in the region and Siena remained small.

Our walking tour ended in front of the Duomo di Siena, or Siena Cathedral, where we were given tickets to enter the church. I knew I would love the Duomo in Florence, but I was completely unprepared for how beautiful this one would be. There is so much to see inside Siena’s Cathedral that it’s hard to know where to start. The outer walls are filled with altars, paintings and stained glass while the floor is covered in mosaics. Many of Italy’s most famous artists are represented here including Bernini, Ghiberti, Pisano and Donatello.

It was hard to leave Siena and I know we will need to return someday in order to explore more of it. But we were also tired and ready to head back to Florence.

Siena Cathedral
Duomo di Siena or Siena Cathedral

Searching for the Best Day Trips From Florence? Check-Out Walks

The company, Walks, was started in Rome but has since expanded to 13 cities in Europe and the U.S. They have developed tours that are a bit different from the offerings of larger companies. They also pride themselves on keeping the groups small and hiring exceptional guides.

This was the first time we had used the company, but it won’t be the last. After researching dozens of day trips from Florence, I know we chose the right one.

Visit Walks and see what tours you can take on your next vacation!

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This Post Has 5 Comments

  1. Andi

    I’ve been lucky enough to have visited Florence 3 times for a week each time, it is such a lovely, walkable city and a great home base for day trips. You can see some good stuff in a day if that is all you have but I highly recommend longer!

    1. Wendy

      Any time in Florence is better than no time–but I’m jealous that you’ve been able to visit three times. I really need to get back and see more in this incredible city.

  2. Ann

    Oh my husband has been trying to get us to Florence for years, but for several reasons that trip just never seems to happen… I think I am going to have to start planning that, maybe for next year 🙂

    1. Wendy

      I highly recommend it! Florence was amazing.

  3. Aditi Sharma

    Ah, beautiful Tuscany. We absolutely loved visiting this charming corner of Italy and your post and all those amazing photographs definitely brought back fond memories. I am so intrigued by the saffron gelato you mentioned – definitely going to try that when we visit again.

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