More about: 4 Best Day Trips to Siena from Florence
Siena, with a historic center declared a World Heritage Site, 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. Tour 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 will 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 journey and 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 is included in this tour
- One day tour Pisa, San Gimignano and Monteriggioni from Florence
- Guide in several languages
- Roundtrip 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 a single day, this excursion to Pisa, Siena and San Gimignano from Florence is perfect for you. You will 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 round-trip bus transportation 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 from the inside one of the most iconic monuments of the country.
What is included in this tour
- Full day tour to Pisa, Siena and San Gimignano from Florence
- Professional guide for the entire tour
- Transportation 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 (pre-booked in advance)
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 at 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 can immerse yourself in Tuscan history, landscapes and gastronomy in a personalized 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 total attention to your interests. 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 center of Florence)
- Transportation 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 in a winery

This tour is my favorite, as it allows you to make the most of your time in Florence by immersing yourself in Tuscany and visiting its main jewels. 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, in addition to 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 that 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, almost 56 meters high and with 294 steps that you can climb to admire unparalleled views of the architectural ensemble of 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 transportation by air-conditioned GT coach 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 winery 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 center, flanked by splendid palaces and historic stores, historic buildings and monuments, among which you can't 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 center of city life.
Duomo of Siena
The 14th-century Cathedral of Siena is a spectacular building with a remarkable baptistery and crypt. It also has magnificent views of the city from its viewpoint, 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 remodeled in the Gothic style.
Palazzo Pubblico
Another place from which to get panoramic views of Siena is from the 88-meter tower of its Palazzo Pubblico, seat of the city council and one of its most representative historic buildings, with a brick and white marble facade.
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 travel style, here is my guide to 10 Best Tours and Daytrips from Florence. Personally, I recommend that 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.