More about: 4 Best Day Trips to Siena from Florence
Siena, with its World Heritage listed historic centre, is one of the wonders of Tuscany that you can visit on a day trip from Florence, as well as Pisa, Chianti, San Gimignano or Monteriggioni.
1. Excursion to Siena, San Gimignano and Monteriggioni with wine tasting

With this guided day trip to Siena, San Gimignano and Monteriggioni, you will discover Siena in depth thanks to a local guide who will take you through this beautiful monumental city, home of the famous Palio horse race. In addition, you can explore on your own the charming medieval town of San Gimignano, halfway between Florence and Siena and known as the 'Manhattan of the Middle Ages' with its skyline of numerous tall medieval towers.
You will also enjoy a typical Tuscan lunch to replenish your energy during your tour, paired with a tasting of local wines at a vineyard in the village of Monteriggioni. This tour is available in several languages, including English, Italian, Portuguese and Spanish, among others.
What this tour includes
- One day tour Pisa, San Gimignano and Monteriggioni from Florence
- Multilingual guide
- Round-trip transportation by air-conditioned minibus or minivan
- Free time
Itinerary
- Siena, with Piazza del Campo, Duomo di Siena
- Monteriggioni
- San Gimignano
2. Excursion to Pisa, Siena and San Gimignano from Florence with optional visit to the Tower of Pisa

If you want to discover some of the most emblematic corners of Tuscany in just one day, this excursion to Pisa, Siena and San Gimignano from Florence is perfect for you. You'll be able to explore three of the region's most fascinating cities, accompanied by a professional guide who will reveal all the secrets of their heritage, history and culture.
In addition to return bus transport from Florence, this experience includes a guided visit to the Cathedral of Siena, a typical Italian lunch with local wine tasting and, if you wish, the possibility of adding the entrance to the Tower of Pisa to discover one of the country's most iconic monuments from the inside.
What is included in this tour
- Full day excursion to Pisa, Siena and San Gimignano from Florence
- Professional guide for the entire tour
- Transport by air-conditioned bus with WiFi
- Included entrance ticket to visit the Duomo of Siena
- Typical Tuscan lunch with tasting of local wines
- Option to include entrance to the Leaning Tower of Pisa (advance booking)
Itinerary
- Pisa, with the option of visiting the Leaning Tower
- Siena and its impressive Duomo
- San Gimignano, one of Italy's most beautiful medieval villages
- Lunch and wine tasting in a local Chianti winery
3. Private tour to San Gimignano, Siena and Monteriggioni

For an exclusive experience in Tuscany, this private tour to San Gimignano, Siena and Chianti from Florence will allow you to explore three of the region's medieval gems at your own pace and in total comfort. Accompanied by a private guide and picked up directly from your hotel, you will be able to immerse yourself in Tuscan history, landscapes and gastronomy in a personalised way.
From the mythical Piazza del Campo in Siena, to the panoramic views of the vineyards of Chianti or the towers of San Gimignano, each stop is designed to allow you to experience the best of Tuscany unhurriedly and with your best interests at heart. Please note that the price is closed for groups of 3 to 7 people, so it is in your best interest to book this option the larger your group is.
What is included in this tour
- Private tour from Florence to San Gimignano, Siena and the Chianti region.
- Hotel pick-up and drop-off (if you are staying in the centre of Florence)
- Transport in luxury air-conditioned vehicle with WiFi on board
- Private guide who adapts the explanations to your interests (in English and 4 other languages)
- Free time in each location to explore at your own pace
- Option to add lunch and wine tasting at a local winery (not included in the price)
Itinerary
- Siena, with stop at the Cathedral and Piazza del Campo
- Chianti region, with views of the vineyards and the possibility of wine tasting
- San Gimignano, with free time to explore its towers and medieval streets
Tuscany tour from Florence to Siena, Pisa, San Gimignano and Chianti, with lunch at a winery

This tour is my favourite as it allows you to make the most of your time in Florence by immersing yourself in Tuscany and visiting its main gems. In one day you will visit the typical Tuscan vineyards in Chianti with a typical lunch and a wine tasting of its Denomination of Origin, as well as touring San Gimignano and visiting the other two Tuscan cities such as Pisa, with its famous Leaning Tower and Siena, with a guided tour.
Pisa is a city that is really worth including in your discovery of Tuscany and which you can visit on your own with this tour. It is home to one of the most famous monuments in the world, the Leaning Tower, which is almost 56 metres high and has 294 steps that you can climb to admire unparalleled views of the architectural ensemble of the Piazza dei Miracoli, with the Cathedral and the Baptistery.
What is included in this tour
- 12 hour excursion from Florence to Siena, San Gimignano, Chianti and Pisa.
- Round trip transport by air-conditioned GT bus with Wi-Fi on board
- English speaking guide and 3 other languages in Siena
- Headphones during the guided tour of Siena
- Entrance to the Cathedral of Siena
- Lunch in a Chianti wine cellar paired with 2 wines of the region
Itinerary
:
- Siena with guided tour
- Chianti with Tuscan lunch
- San Gimignano
- Pisa
Why a trip to Siena is worthwhile

Siena is a magical city in which to lose yourself in the narrow medieval streets of its historic centre, flanked by splendid palaces and historic shops, historic buildings and monuments, among which you should not miss:
Piazza del Campo
This medieval square, one of the most beautiful and largest in the world, hosts the famous ancient horse race of the Palio of Siena and is the centre of the city's life.
Duomo of Siena
The 14th century Cathedral of Siena is a spectacular building with a remarkable baptistery and crypt inside. It also boasts magnificent views of the city from its belvedere, the 'Panorama del Duomo'.
Church of San Domenico
This is the second most important church in Siena. With a sober appearance due to its brick construction, the Church of San Domenico was erected in the 13th century and later remodelled in the Gothic style.
Palazzo Pubblico
Another place to get panoramic views of Siena is from the 88-metre tower of its Palazzo Pubblico, the seat of the city's town hall and one of its most representative historic buildings, with its brick and white marble façade.
Other interesting activities in Florence
If this article on how to visit Siena from Florence has been useful for you or if you are still not sure which excursion best suits your style of travel, here is my guide on how to visit Siena from Florence. 10 Best Tours and Daytrips from Florence. Personally, I recommend you consider Cinque Terre or Pisa as alternative destinations to Siena. Here are the articles I have written about them: Day Trips to Cinque Terre from Florence y 5 Best Day Trips to Pisa from Florence.