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Best Tours of Siena

The Italian city of Siena is known for its beauty and rich history. Don't miss a single one of its many attractions and take one of the best tours that this wonderful city has to offer.

Nicolas Reffray

Nicolas Reffray

10 min read

Best Tours of Siena

Siena | ©Skitterphoto

With its medieval buildings, cobblestone streets and sites such as the Piazza del Campo, the Palazzo Pubblico, and the Torre del Mangia, Siena is a city that has a lot to offer to those who visit it. Nothing better to get the most out of your visit than to take a guided tour.

There are many things to see and do in the city of Siena, you will see that there are options for all tastes, from walks through the historic center of the city or Vespa motorcycle rides, to tours aboard a classic Fiat 500 through the Tuscan countryside. Here I have selected for you all the options that await you in this interesting city.

1. Tour Siena on a Vespa and have lunch in a Chianti winery

Vespa| ©BrotherSnare
Vespa| ©BrotherSnare

If you are looking for an all-inclusive experience, maybe this is your best choice. On this tour you will ride through the Tuscan countryside on a classic Vespa scooter towards the Chianti Valley. On this very Italian ride, you will have the opportunity to appreciate the Tuscan hills, the vineyards and wineries, as well as the picturesque medieval villages.

At noon you will stop at a renowned winery. There you will enjoy a traditional Italian lunch, accompanied by the best wines produced in the winery, and then return to Siena.

Let me tell you that if the world of wine interests you, you have found the perfect destination. I recommend you also take one of the best wine tours in Siena, they are absolutely amazing.

This is a full day activity, and it is suitable whether you know how to drive a motorcycle or not, since in that case you can ride behind the driver as a companion.

Details of interest:

  • Price: from 124 euros per person.
  • Duration: about 7 hours and 30 minutes in total.
  • Means of transport: you will tour Tuscany on a classic Vespa scooter.
  • Advantage of this option: it offers pick-up from the place where you are staying.
  • Disadvantage of this option: it can be cancelled due to weather conditions.

Book a wine tour in Siena

2. Take a tour of San Gimignano, Chianti and Montalcino

San Gimignano| ©Steph Gray
San Gimignano| ©Steph Gray

Take this day tour to San Gimignano, Monteriggioni and Montalcino, where you will enjoy medieval architecture, majestic panoramic views and delicious wines. You will depart from Siena aboard an air-conditioned minibus in a small group of up to 8 people.

You will make stops at sites such as the Collegiata di Santa Maria Assunta, the Duomo di San Gimignano, the Piazza della Cisterna, the Palazzo Pubblico, the Torre Grossa and the Fortezza di Montalcino, where you will have free time to explore at your own pace.

At noon you will enjoy a delicious regional lunch and wine tasting at a winery in Montalcino. At the end of the day you will have an hour at your disposal in the majestic Orcia Valley, to be fascinated by its immensity and take the best photos.

Details of interest:

  • Price: from 101 euros per person.
  • Duration: the tour lasts 11 hours in total.
  • Means of transport: air-conditioned minibus.
  • Advantage of this option: the guides know several languages.
  • Disadvantage of this option: it is not adapted for wheelchair users.

Book a day trip to San Gimignano, Chianti and Montalcino

3. Get to know Siena Cathedral in depth

Siena Cathedral| ©Discovering the Globe
Siena Cathedral| ©Discovering the Globe

Undoubtedly, the Cathedral is one of the most iconic places in Siena, one of those that you should not miss if you are in the city. On this tour you will get to know it in the most complete and convenient way. You will go in a small group together with your guide, who will tell you the story behind its construction and all its surroundings.

The guided tour and access to the Cathedral of Siena also has the advantage that, thanks to having the tickets booked in advance, you will avoid having to wait in long lines. Afterwards, your guide will take you to walk around the surroundings of the Siena Cathedral, where you will enjoy some beautiful piazzas, hidden gardens and the medieval quarters of Siena.

Details of interest:

  • Price: from €36 per person.
  • Duration: about 2 hours and a half in total.
  • Means of transport: the tour is done on foot from a meeting point.
  • Advantage of this option: you will know every detail of one of the architectural jewels of Siena.
  • Disadvantage of this option: the visiting hours are fixed and no refreshments are included during the tour.

Book a tour of the Cathedral of Siena

4. Drive an antique Fiat 500 through the Tuscan hills

Monteriggioni| ©Michela Simoncini
Monteriggioni| ©Michela Simoncini

If you have always dreamed of driving a Cinquecento through the Italian countryside, this tour is for you. You will have the opportunity to take a picturesque ride aboard this classic Italian automobile. You will be picked up at a point located in the historic center of Siena, to head towards the town of Monteriggioni through the Tuscan roads.

You can drive yourself, or be accompanied by a driver. The caravan of cars will be led by the group guide. On the tour you will cross the Chianti hills and marvel at the breathtaking scenery of the Italian countryside.

The tour makes a stop at one of the local vineyards to taste their delicious wines and recharge your batteries with a hearty three-course lunch of regional food. Groups are limited to a total of 10 people, so the experience is personalized. You'll be able to take full advantage of your guide's knowledge and explanations.

Details of interest:

  • Price: from 150 euros per person.
  • Duration: about 7 hours and 30 minutes in total.
  • Means of transport: the vehicle is a classic Fiat 500 car.
  • Advantage of this option: you will have the opportunity to experience a classic, you will drive through the countryside of Italy aboard one of the most iconic cars of the country.
  • Disadvantage of this option: some parts of the excursion are not suitable for people with reduced mobility or wheelchairs.

5. Get to know Chianti by bike and have lunch in a winery

Chianti| ©denis legendre
Chianti| ©denis legendre

If you like to ride a bike, this tour will allow you to do so while enjoying the beautiful landscapes of Tuscany. Your guide will pick you up from your accommodation in Siena and take you aboard a van to Chianti, where your bike and helmet are waiting for you.

Once you are ready, you will set off with your group and your guide to tour the Chianti area. Through the rural landscape you will see all the wonderful Tuscan nature, visit an ancient monastery, then stop at a winery. The stop includes a traditional lunch and a wine tasting.

This is an ideal ride for those who enjoy physical exercise and touring the sites in a more interactive way with the environment. Dare to pedal through Tuscany! And if you would like to take the tour, but doubt if you can handle the exercise, don't worry, since these are electric bikes, you choose the level of effort.

Details of interest:

  • Price: from 159 euros per traveler.
  • Duration: about 6 hours in total.
  • Means of transport: air-conditioned van and on-site mountain bike.
  • Advantage of this option: the groups are small and you will have the pleasure of pedaling along the paths next to the vineyards.
  • Disadvantage of this option: not suitable for people with disabilities or physical limitations.

Book a bike tour in Chianti

6. Discover the best of Siena walking through its streets with a guide

Piazza del Campo| ©Hervé Simon
Piazza del Campo| ©Hervé Simon

This is a great option to get to know the most important sites of Siena with a specialized local guide. You will walk through the historic cobblestone streets of the medieval old town and appreciate emblematic sites such as the Basilica of San Domenico, the Sanctuary of St. Catherine of Siena, Piazza del Campo and the imposing Cathedral.

On this walking tour you will also see important works of Renaissance artists, along with the stunning architecture of the city, so it is ideal if you want to see Siena in 1 day. The groups are small, so the experience is much more personalized and you will be able to make the most of all the information. This is an excellent way to tour Siena without missing out on any of its main attractions.

Details of interest:

  • Price: starting at €140 per person.
  • Duration: about 3 hours in total.
  • Means of transport: on foot, there is no pick-up service, but you have very accessible public transport in the area.
  • Advantage of this option: You will be able to walk through the old town with a local guide, which guarantees you to know those places that would otherwise escape you.
  • Disadvantage of this option: it does not include the entrance to the Cathedral or the Contrada Museum, if you wish to enter you can still buy your ticket on the spot.

7. Discover the secret side of Siena

Basilica di Santa Maria dei Servi| ©Pedro
Basilica di Santa Maria dei Servi| ©Pedro

Designed for those who already know the typical sights of Siena, this tour takes you a little deeper into the rich heritage of the city. With a small group and a professional guide you will walk through other attractions. You will be led through the areas less crowded with tourists and walk through alleys and streets that will make you feel like a local.

You will learn about some of the details of Siena's golden age of architecture and visit sites such as the Church of the Madonna di Provenzano and the Basilica di Santa Maria dei Servi. The latter houses masterpieces of enormous value.

You will learn about the history of some prominent local artists, the neighborhoods and districts of Siena, and of course the Palio di Siena race. You will also visit the medieval Fontebranda fountain where the guide will tell you about the geology of the area.

Details of interest:

  • Price: from €30 per person.
  • Duration: about 3 hours in total.
  • Means of transport: on foot, you will have to reach the starting point by your own means. Fortunately, public transportation is accessible in the area.
  • Advantage of this option: you will be able to enjoy a tour outside the classic, you will get to know another Siena.
  • Disadvantage of this option: you must be in good physical condition, as the walk is intense.

8. Delight yourself with the Italian opera

Italian Opera| ©Carlo Raso
Italian Opera| ©Carlo Raso

There is nothing better than enjoying a city with all your senses. With this tour you can delight in listening to the best of Italian opera. You will witness a live opera performance, during a fantastic evening.

In the concert the singers perform classic arias from famous operas, such as Il barbiere di Siviglia, Madame Butterfly, La Traviata and La Bohème among others. All in an imposing venue, the ancient baroque church Chiesa di Santo Stefano alla Lizza, which stands out for its impressive acoustics.

Details of interest:

  • Price: from €27 per person.
  • Duration: about 1 hour and a half in total.
  • Means of transport: the meeting point is easily accessible by public transport.
  • Advantage of this option: as it is an organized tour, you will not have to wait in line. You will have the opportunity to listen to some of the classics of the genre in an ideal environment.
  • Disadvantage of this option: refreshments and a glass of wine are not included.

9. Spend a day in Montepulciano and Pienza

Montepulciano| ©thy
Montepulciano| ©thy

Montepulciano and Pienza are two medieval settlements very close to Siena, which have been declared UNESCO World Heritage Sites. On this full day guided excursion from Siena you will enjoy not only the breathtaking Tuscan scenery and beautiful villages, but also delight in the flavors of the region's cuisine. The tour includes lunch with Pecorino cheese tasting.

If you wish, you can also visit a winery in Montepulciano, where you can taste and buy its best wines. The experience takes place in small groups of 8 people maximum, so the atmosphere is extremely relaxed and almost personalized.

Details of interest:

  • Price: from 173 euros per person.
  • Duration: about 8 hours in total.
  • Means of transport: air-conditioned minibus.
  • Advantage of this option: you will visit two of the most beautiful medieval villages of Tuscany, declared World Heritage Site by UNESCO.
  • Disadvantage of this option: it is not adapted for wheelchair users.

10. Dare to go for a walk in Tuscany

Tuscany by night| ©Alex Berger
Tuscany by night| ©Alex Berger

This is the ideal option for hiking lovers and those who enjoy walking through the sites to enjoy them at a leisurely pace. Your guide will pick you up in a comfortable air-conditioned minivan to take you to Tuscany and start the adventure.

On your way you will learn from your guide about the history and nature of the region. You will walk through olive groves, alongside hills and vineyards, and pass through ancient and idyllic villages that will make you feel like you have traveled back in time.

You will have a refreshment stop where you will have a picnic lunch with the best of regional preparations, country bread, cheese, Serrano ham and fresh vegetables, plus a glass of the most delicious wine. And if that's all it takes to whet your appetite, you should check out the best food tours in Siena.

The tour includes stops on the Via Francigena, an ancient medieval pilgrimage route, and the picturesque town of San Gimignano. Undoubtedly a tour that becomes an unforgettable experience.

Details of interest:

  • Price: values start from 50 euros per person.
  • Duration: about 4 hours in total, approximately.
  • Means of transportation: air-conditioned minivan with capacity for 8 passengers.
  • Advantage of this option: the cost includes a picnic with a glass of wine.
  • Disadvantage of this option: the activity is not suitable for people with physical limitations, walking difficulties or heart and respiratory conditions.