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 this wonderful city has to offer.

Nicolas Reffray

Nicolas Reffray

10 min read

Best Tours of Siena

Siena | ©Skitterphoto

With its medieval buildings, cobbled 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 visitors. Nothing better to get the most out of your visit than a guided tour.

There are many things to see and do in the city of Siena, and you will see that there is something for everyone, from walks through the historic city centre, to Vespa motorbike rides, to tours on board 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 wine cellar

Vespa| ©BrotherSnare
Vespa| ©BrotherSnare

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

At midday you will stop at a renowned winery. There you can enjoy a traditional Italian lunch, accompanied by the best wines produced on the premises, before returning 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 is suitable whether you know how to drive a motorbike or not, as in that case you will be able to 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: offers pick-up from the place where you are staying.
  • Disadvantage of this option: 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'll 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 midday you will enjoy a delicious regional lunch and a wine tasting at a winery in Montalcino. At the end of the day you will have one hour at your disposal in the majestic Orcia Valley, to be fascinated by its immensity and take the best pictures.

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: 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 Siena Cathedral also has the advantage that, thanks to having your tickets booked in advance, you will avoid having to wait in long lines. Afterwards, your guide will take you around 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 2.5 hours in total.
  • Means of transport: the tour is done on foot from a meeting point.
  • Advantage of this option: You will get to know all the details of one of Siena's architectural jewels.
  • Disadvantage of this option: the visiting hours are fixed and no refreshments are included during the walk.

Book a tour of the Cathedral of Siena

4. Drive a vintage Fiat 500 through the Tuscan hills

Monteriggioni| ©Michela Simoncini
Monteriggioni| ©Michela Simoncini

If you've always dreamed of driving a Cinquecento through the Italian countryside, this tour is for you. You'll have the opportunity to take a scenic drive in this classic Italian automobile. You will be picked up at a point located in the historic centre 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 stops at one of the local vineyards to taste delicious wines and recharge your batteries with a hearty three-course regional lunch. Groups are limited to a total of 10 people, so the experience is personalised. You'll be able to make the most 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, driving through the Italian countryside in one of Italy's most iconic cars.
  • Disadvantage of this option: some parts of the tour are not suitable for people with reduced mobility or wheelchairs.

5. Discover Chianti by bike and have lunch in a winery

Chianti| ©denis legendre
Chianti| ©denis legendre

If you enjoy cycling, this tour will give you the opportunity 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 will be waiting for you.

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

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

Details of interest:

  • Price: from 159 euros per passenger.
  • Duration: about 6 hours in total.
  • Means of transport: air-conditioned van and on-site mountain biking.
  • Advantage of this option: the groups are small and you will have the pleasure of cycling 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 way to see the most important sites of Siena with a local guide. You will walk through the historic cobblestone streets of the medieval old town and see iconic sites such as the Basilica of San Domenico, the Sanctuary of St. Catherine of Siena, the Piazza del Campo and the imposing Cathedral.

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

Details of interest:

  • Price: from 140 euros per person.
  • Duration: about 3 hours in total.
  • Means of transport: on foot, there is no pick-up service, but public transport is very accessible in the area.
  • Advantage of this option: You will be able to walk around the old town with a local guide, which guarantees you will see those places you would otherwise miss.
  • Disadvantage of this option: it does not include entrance to the Cathedral or the Contrada Museum, but 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 explore other attractions on foot. 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 neighbourhoods 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 euros per person.
  • Duration: about 3 hours in total.
  • Means of transport: on foot, you will have to get to the starting point by your own means. Fortunately, public transport is accessible in the area.
  • Advantage of this option: you will be able to enjoy an unusual tour, 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 is noted for its impressive acoustics.

Details of interest:

  • Price: from 27 euros 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 organised tour, you will avoid queues and annoying waits. You will have the opportunity to listen to some of the classics of the genre in an ideal setting.
  • Disadvantage of this option: refreshments and a glass of wine are not included.

9. Spend a day at Montepulciano and Pienza

Montepulciano| ©thy
Montepulciano| ©thy

Montepulciano and Pienza are two medieval settlements very close to Siena, which have been declared World Heritage Sites by UNESCO. On this full day guided tour from Siena you will enjoy not only the breathtaking Tuscan landscapes and beautiful villages, but you will also be able to indulge in the flavours 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 the best wines. The experience takes place in small groups of 8 people maximum, so the atmosphere is extremely relaxed and almost personalised.

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 get to know two of the most beautiful medieval villages of Tuscany, declared World Heritage Sites 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 hikers 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 about the history and nature of the region from your guide. You will walk through olive groves, alongside hills and vineyards, and pass through ancient and idyllic villages, which will make you feel like you have travelled back in time.

You will have a refreshment stop for a picnic lunch with the best of regional delicacies, 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. Without a doubt a tour that becomes an unforgettable experience.

Details of interest:

  • Price: values start from 50 euros per person.
  • Duration: about 4 hours in total.
  • Means of transport: 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.