Things to do in Siena, Tuscany: The Best City Tours

April 29, 2022 Osvaldo Hartline

This Tuscan hill town will transport you back to the Middle Ages. Siena's grand cathedral, built in the 1200s, has treasured artworks and marvelous marble floors. The Piazza del Campo, the main town square, is a UNESCO World Heritage Site. It's also home to the Palio, perhaps the most infamous horserace in the world. No goofy hats and mint juleps here—this is a medieval tradition involving bareback riders racing on cobblestones (so as you might imagine, it's quite dangerous). Siena is an easy daytrip by train from Florence, just 43 miles away.
Restaurants in Siena

1. Private Tour: Siena Walking Tour

Siena, Siena, Tuscany Tour Guide Siena and Province
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5.0 based on 30 reviews

Siena, 'the pearl of the Gothic style,' is a charming medieval town in the center of Tuscany. Come and discover the hidden treasures of this medieval town and the surroundings with a professional tour guide.

Inclusions: Professional guide

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Reviewed By vic10101

I have visited so many cathedrals and structures in Europe and this is one of the most fascinating. It’s design, the art on flooring, the sculptures, the paintings, the architecture — these make the cathedral of the most magnificent structures made. How religions can inspire such structure is amazing.

2. The best of Siena - Private Walking Tour

Basilica Cateriniana San Domenico, Piazza San Domenico, 1, 53100 Siena SI, Italy Demetra Tour Guide of Florence and Tuscany
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5.0 based on 3 reviews

Enjoy a private walking tour around Siena, a smart medieval city center that has been declared by UNESCO a World Heritage Site.

Inclusions: Local guide, private licensed guide

Exclusions: Transportation to/from attractions, Hotel pickup and drop-off

Reviewed By Clarissa D

Demetra was a wonderful and accommodating guide. I thoroughly enjoyed the tour and our time together. Had the chance to speak to, and learn from, the various artisans that we visited. All of whom I would not have known to visit or see if Demetra had not shown the way!

3. Private Walking Tour: Siena and its Treasures

Il Campo, 53100 Siena SI, Italy ABCD Tours of Tuscany
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5.0 based on 1 reviews

Discover Siena with a professional guide on this private tour to admire the beauty of this Tuscan town, like its Cathedral, the Baptistery and Opera Museum... Remember to take your camera  to take some pictures from the high Facciatone, one of the best panoramic site.

Inclusions: Professional guide, Private tour

Exclusions: Transportation to and from attractions, Hotel pickup, Entrance museums fees

Reviewed By Alexander12347

Cecilia is an exceptional tour guide, probably the best we have ever had. She gave us a extremely interesting and thorough tour of the Palazzo Vecchio. Her knowledge of city is very in-depth. She Is also a lovely person and very pleasant company. Grazie Cecilia! We’ll be back!

4. Minivan Tour to Siena and San Gimignano from Florence

Piazza dei Cavalleggeri, 50122 Firenze FI, Italy ACCORD Italy Smart Tours & Experiences
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5.0 based on 2 reviews

During this small- group  tour in a comfortable minivan, you will explore the breathtaking towns of Siena, Monteriggioni, and San Gimignano. All are symbols of Medieval and Gothic architecture, characteristic elements are the historic towers, pointed arches, and narrow streets. Moreover this Tuscan area is full of superb food specialties you will surely have the chance to taste, such as Panforte and Pici. The tour lasts 8 hours with 2 hours spent in Siena, a short visit in Monteriggioni for a photo stop, and approximately 1 hour in San Gimignano.You will also get a detailed description from our expert local guide in Siena.

Inclusions: Professional local guide in Siena - 1 hour, Air-conditioned minivan + english speaking driver

Exclusions: Guide in San Gimignano (upon request), Food and drinks, unless specified

Reviewed By sandyc17

My husband and I did this tour and it was fabulous - the driver was great and there were only four of us so you could talk away to the driver - we scooted through the city easily on the golf cart and it was such good fun and we saw loads of amazing stuff, I’d highly recommend this tour

5. From Florence to Siena - San Gimignano & Pisa by private minivan

Piazza dei Cavalleggeri, 50122 Firenze FI, Italy ACCORD Italy Smart Tours & Experiences
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5.0 based on 2 reviews

The tour starts with a ride by air-conditioned minivan and an English speaking driver from Florence to Siena.  First Stop at Piazzale Michelangelo for a wonderful Panorama over the city.  Than take the Motorway to Siena. In about 1 Hour you will be in Siena and meet our guide to start your visit of the old Town. You will se the famous Piazza del Campo where the famous Palio takes place every year. Continue the visit along the narrow Medieval Street to reach the Cathedral and visit ( closed on Sunday ). Free time in Siena and departure to reach San Gimignano where you will have free time to walk around the city centre.  After lunch (not included in the price) you will visit Pisa: the city is known for its bright monuments, which includes the 11th-century Cathedral, the Baptistery and the Leaning Tower.You will have free time to stroll around the city before leaving to come back to Florence.

Inclusions: Chauffeured air-conditioned vehicle 10 hrs, English speaking driver, 1 hour guided tour in Siena and 30 minutes in Pisa, free time in San Gimignano, WINE TASTING AND LIGHT LUNCH IN A FARMHOUSE

Exclusions: Food and drinks

Reviewed By sandyc17

My husband and I did this tour and it was fabulous - the driver was great and there were only four of us so you could talk away to the driver - we scooted through the city easily on the golf cart and it was such good fun and we saw loads of amazing stuff, I’d highly recommend this tour

6. Siena 2-hour private tour with an expert guide

Converse, Il Campo, 30, 53100 Siena SI, Italy Siena Faberest
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5.0 based on 1 reviews

On this private guided walking tour you'll explore a town which was declared by UNESCO a World Heritage Site. You'll see its main and beautiful sites, like Siena Cathedral, Piazza del Campo, Torre del Mangi, Fonte Gaia, Piazza del Mercato and much more!

Inclusions: Expert guide, Private tour

Exclusions: Entrance tickets to museums/attractions/churches (in case you decide to visit the interiors of some of them), Food & drinks

7. Private tour Siena, San Gimignano and Monteriggioni

Florence, Metropolitan City of Florence, Italy Driver Florence
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5.0 based on 1 reviews

Spend a day in Tuscany visiting the city of Siena, the castle of Monteriggioni and the medieval village of San Gimignano. With a private English speaking driver, you will enjoy more flexibility in your itinerary with lots of free time. Enjoy a stroll through the historic center full of history of Siena and then admire the view over the Tuscan countryside from San Gimignano. End the tour with a visit to Piazzale Michelangelo before returning to Florence.

Inclusions: Private transportation, Air-conditioned vehicle, WiFi on board, Natural water is available inside the minivan, available to customers from the minibar., English speaking driver

Exclusions: Lunch only on request (paid separately), Tourist guide only on request (paid separately), Gratuities, Admission tickets (for the Duomo of Siena at about € 7 per person)

Reviewed By PM770

Florian is very punctual, prompt in his replies to mails, excellent driver and very cooperative. His car is also in top condition. We did a Pisa and Cinque Terre trip with him on 20th May. He also helped us with restaurants and finding a good guide. 5/5 to him. P Muthal

8. Siena, San Gimignano & the Chiantiside private tour with Mercedes V class Van

Bespoke Italian Tours
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5.0 based on 3 reviews

Our tour is made with passion by expert english speaking drivers who know everything about the area. We will start with Siena, a Medieval & Reinassance gem, famous for its stunning sights and impressive buildings. We will stop by the best places to take pictures, dropping you off in front of the amazing cathedral (the highest point of the city). From there you'll take a delightful stroll down to the Piazza del Campo, the main square with its beautiful bell tower, than walk up to the Salimbeni square, headquarter of the oldest still operating bank in the world. From there we will meet again and drive to a beautiful farm in the hills, to have the best lunch with local wines. After that we will take a scenic drive to San Gimignano, the Manhattan of Tuscany, famous for the house towers, the white Vernaccia wine, the golden saffron and the best Gelato in the world. From there we will take a relaxing drive back to your place, making extra stops if we finished early!

Inclusions: WiFi on board, Air-conditioned vehicle, Private transportation, Bottled water, Fuel surcharge, Parking Fees

Exclusions: Lunch in family run winery is 50€ per person with wine tasting

Reviewed By F5679VVchriss

Amazing experience. Niccolo picked us up at our villa and took us on a wonderful tour of Tuscany and two excellent wineries, with one of them also hosting us for lunch. He is an articulate guide and provided multiple recommendations to enhance the remainder of our family trip. I would recommend Niccolo and his company without hesitation to anyone looking for a great time in Tuscany. Thanks Niccolo.

9. Private Day Trip from Rome to Siena and San Gimignano

Rome First Choice Tours
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5.0 based on 1 reviews

Discover The Beauty Of Siena And San Gimignano, Traveling Through The Countryside Of The Chianti Region, With Ever Changing Scenery Of Vineyards And Olive Trees On This Full Day Private Trip From Rome. Since It Is A Private Tour So The Itinerary Is Flexible And You Can Change It As You Want , Your Driver Will Always Give You The Right Suggestions According To Your Preference

Inclusions: Transportations, Expert Driver/Guide, Pickup-Drop-off / From-To Hotel, Fuel surcharge, Parking Fees

Exclusions: Attraction Tickets if any, Gratuities , Wine tasting and lunch ( cost is 30 Eur per person to be paid at the winery )

Reviewed By Abdelmoneim

Assem is the best tour guide ever. The tour was so informative, funny and exclusive. You live the history and know small details that make you value the Colosseum. Don't forget to take photos everywhere.

10. Private Tour of San Gimignano & Siena

Paola's Florence Tours
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5.0 based on 2 reviews

We are Italian local guides, born in Florence and you will have a unique Tuscany experience, this is a perfect day to relax after enjoying the countryside and to celebrate family moments. We have licensed vans to enter in all traffic limited area and we are drivers and licensed guides and you will be guided while driving and walking.

Inclusions: Air-conditioned vehicle, Private transportation, Licensed local guide

Exclusions: Lunch, Gratuities, Entrance fees

Reviewed By MarcodelaPierre

Even if I'm from Florence it was incredibly interesting to visit the Accademia Museum (the one with the famous David inside) with Paola....I learnt so much about Michelangelo's life....his personal story and his philosophy! It was an Amazing tour in my city and I really loved it! Recommended for everybody!

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