How to plan your Florence to Siena day trip

Siena, the city of the Palio

During your stay in Florence, you certainly want to have a Florence to Siena day trip. There are many reasons why you want to visit Siena. It’s a charming city in the heart of Tuscany, filled with stunning architectural attractions, where the Medieval traditions seem to never end. one above all: the Palio di Siena, a horse race taking place in the main square of the city, Piazza del Campo, twice a year, on July 2nd and August 16th. And Piazza del Campo is the main public space of the historical center of Siena: the shell-shaped square is one of the most suggestive places in Tuscany, rivaling the famous Piazza Della Signoria in Florence. For all the Middle Ages and part of the renaissance, Siena and Florence were indeed rivals, until when, in 1559, Cosimo de Medici extended his territory conquering the city of the Palio and unifying Tuscany. The Palazzo Pubblico towers on the square adapting to the shape of the open space with its curved facade, and all the square is surrounded by historical palaces in gothic style. The Duomo of Siena (Cathedral of Santa Maria Assunta) is another 13th-century gothic wonder, decorated in white and black marble, to recall the symbolic colors of the city. Inside, it is an extraordinary museum of Italian sculpture, with works by Donatello, Michelangelo and Bernini. There are many more artistic attractions in Siena, but the great bonus of the city is its territory, featuring the most typical Tuscan landscape, made of hills filled with vineyards and ancient villages, one above all: the village of San Gimignano, an enchanted place that still preserves most of his ancient tower-houses. If you have to choose a day trip from Florence, Siena is a top choice.

Florence to Siena day trip: half day

There are some half day proposals for a Florence to Siena day trip, and most of them are in the afternoon, including a dinner. This is a very good way to visit Siena from Florence in my opinion: if you have limited time in Florence, like many travellers do, this way you have the morning to do something in Florence, where attractions and things to do seem to never end, and then you can relax and enjoy one of the most beautiful sunsets of your life in the heart of Tuscany. Let’s go through the various tours offered, I’m sure you will find the best for you.

Florence to Siena day trip in the afternoon, including San Gimignano and Chianti dinner

Tuscany Small-Group Day Trip with Chianti Dinner: Siena and San Gimignano

The first proposal we are going to review is a small group half day trip from Florence to Siena and San Gimignano with dinner in the Chianti included. It’s a rather expensive tour, but offers a lot and in my opinion it’s your best choice for a Florence to Siena day trip including San Gimignano. I like the itinerary and the pace is fine: you can enjoy Florence in the morning and then meet your small group (up to 16 people) in central Florence at 1:45 pm, hop on your minibus and relax while the driver gets you to Siena. During the short trip (Siena is less than 60 km away from Florence), you will have a chance to enjoy the beautiful Tuscan landscape. In Siena, a professional guide will provide a walking tour of the city, including Piazza del Campo and the backstreets filled with typical shops. You will be given a “surprise” taste of one of the many local specialties: Siena is famous for its desserts, eaten in all of Italy especially during the Christmas festivities, like panforte and ricciarelli. After visiting Siena, your minibus will drive you to San Gimignano, where you will have about one hour of free time to walk and shop around, admiring the Medieval towers. Finally, you will reach a wine estate where you will have a chance to see the sunset (let’s hope the weather is good). Here you will be served a complete meal with wine, consisting of three courses: a bruschetta, which is a typical Tuscan snack consisting in a slice of bread with extra-virgin olive oil and salt, then a dish with cheese and local cold cuts of pork, and finally the main course where you can choose between the ribollita (the most typical Tuscan soup) and lasagne. I plead you: don’t be a tourist and choose the ribollita! The dinner ends with a typical Tuscan dessert, the cantucci di Prato with a glass of Vin Santo (a sweet wine for dessert). Get back to Florence around 11 pm, in Piazza Della Repubblica. Can you ask for more? Book this tour before I do!

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Florence to Siena day trip in the afternoon, including Chianti region and dinner in Piazza del Campo

Sunset Siena and Chianti Wine Tour with Dinner from Florence

This is a well organized, not expensive and not too fast paced Florence to Siena day trip which I recommend for the wine lovers. It includes both art and history and food and wine, but if wine, in particular, is your passion, then read about the tours from Florence to Tuscany countryside. If you are interested more in shopping, wine, food but still want some art and history, you will be pleasantly surprised by this tour, even though it doesn’t involve a professional guide for your time in Siena (you’ll be on your own), nor a visit to San Gimignano. You will, by the way, have a tour leader that can give you directions and suggest what to see or where to go. The tour will leave Florence (close to Santa Maria Novella train station) at 3 pm when your private coach will drive you to Siena. In the city of the Palio you will have about 2.5 hours of free time to stroll in Piazza del Campo, see the Duomo (entrance fee not included) and explore the narrow Medieval streets filled with typical shops. Once back to your coach, you will be driven to a wine estate in the Chianti region, where you will have a chance to visit the cellars. Be advised not to speak loud in the cellars, as the vibrations could disturb the process of aging. This and many more particulars about the complicated process of production of the Chianti wine will be explained to you by an expert. Finally comes the main event of the tour: a complete dinner with wine tasting in the beautiful main farm of the estate: you will not only taste typical Tuscan food, but the wine produced in that same farm, with your tour leader explaining you the different features of each glass of wine (up to four… more than enough to come back “happy”). You’ll be back in central Florence around 10:30 pm. If you love to walk around beautiful places with no stress and love wine and food, book this tour and rest assured you won’t regret it.

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Florence to Siena day trip: full day

The full day offers for a Florence to Siena day trip are better suited for who has more time in his vacation to Florence. At least three nights I would say, because there is a lot to see in Florence. Anyway, if you have a passion for traveling and you are of the kind that gets bored soon when staying in one place, these trips are for you. A longer Florence to Siena day trip has the advantage that you won’t be rushed and you will enjoy in full your time in the beautiful heart of Tuscany. Below you’ll find the best offers I personally selected for your full day experience.

Siena and San Gimignano day trip from Florence

This is the most popular Florence to Siena day trip; I recommend it for the art and history lovers. Certainly, having a very low price is part of the popularity, and, of course, it means that some of the bonuses you had in the previous tours won’t be offered in this one. The tour offers wine (one glass) and food (traditional sweets) tasting, but no complete meal is provided, so you have to consider the expense for lunch. The trip starts from central Florence, near the Santa Maria Novella train station, at 9 am. A private coach will get you to Siena with live commentary on board. A professional guide of Siena will show you the San Domenico Basilica inside (entrance fee included), the historical places of the city and one of the contrade museum (the contrade are the districts of the historical centre that challenge each other in the Palio, the famous historical horse race), you will get to know how the Palio works and why it’s something that makes the city crazy during the Summer (if the museum is closed for any reason, a visit inside the Cathedral or any other main attraction will replace this part of the tour). After lunch, which is on your own and at your expense, you will hop on the coach again to be driven to San Gimignano. You will visit the San Gimignano 1300 museum, where artists reproduce miniatures of the ancient town in terracotta, which are then painted. Then you will have time to relax tasting a glass of Vernaccia (the typical white wine of San Gimignano) accompanied by panforte and ricciarelli, two typical sweets of the territory. You will be back to Florence around 7 pm, in the same place where the trip started. Although it doesn’t offer a complete meal, this Florence to Siena day trip offers a lot more than any other else in terms of art and history. Add the very competitive price to the equation and, if you love art and history, book this tour because this is your best choice for a full day trip.

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Pisa, Siena and San Gimignano day trip from Florence including lunch

Choosing a 14 hours Florence to Siena day trip is something to ponder about, but if you have limited time and don’t want to miss either Pisa or Siena, this is a good choice with a very reasonable price. Well actually an amazing price, given what is included. So don’t expect excellent food for lunch, expect a large group instead and prepare to stay on the coach for a long time and in the cities for a short time, because Pisa is not exactly along the way coming back from Siena. Once you know and accept this, you will be on the right way to enjoy what this tour has to offer. If not, then I suggest you choose another Florence to Siena day trip and add Pisa to a Cinque Terre day trip from Florence, or go to Pisa with a dedicated day trip: you can find more info in my article about choosing a Pisa tour from Florence. This Florence to Siena day trip starts from Piazza Adua in Florence, close to the Santa Maria Novella train station, at 8 am. You will be driven to Siena, where a professional tour guide will entertain you showing the main attractions of the city, and the Duomo inside (entrance fees included, not many trips to Siena have this bonus). Lunch will happen in a local winery or restaurant, will be made of three courses plus samples of two to three wines. After this break, you will hop on your coach to reach San Gimignano, where you will be given some time to explore the village independently. After rejoining the group, you will be driven to Pisa where you will have a chance to see the Leaning Tower and the other attractions like the Duomo and Baptistery, on your own (no guide). Finally, the coach will drive you back to Florence around 10 pm. A wearisome but comprehensive tour: if you don’t want to miss anything and have limited time, book this tour.

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