10 Private Tours in Siena That You Shouldn't Miss

September 28, 2021 Misti Hsu

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 Siena to Florence Chianti and San Gimignano Transfer Tour

53100 Siena, Province of Siena, Italy Tuscan Escapes
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5.0 based on 3 reviews

Travel between destinations and visit sights along the way. Stop to visit the medieval fortress of Monteriggioni before spending leisure time in the hill-town of San Gimignano browsing the many stores or savouring the rich cuisine in one of its many restaurants (not included). In the afternoon visit the Chianti town of Greve in Chianti and the picturesque hamlet of  Montefioralle before having your Private driver drop you off at your Florence destination.

Inclusions: Private Transportation in air-conditioned minivan, Driver/guide, Live commentary on board, Siena Hotel pickup, Florence Hotel drop-off

Exclusions: Lunch, Gratuities

Reviewed By Pioggiola

We did a 3-hour private tour of Siena with Giorgia this summer with our two teenage children. It was just perfect! Giorgia is extremely knowledgeable about all aspects of Siena and beyond, and it clearly showed in the depth of her answers to the very many questions that we asked. She was flexible to adapt the tour based on what we were interested in. Although not originally from Siena, she knows and loves the city like a local and has the ability to make the tour unforgettable. 160 Euros for a fantastic private our of Sienna. Very good value for money. Probably the best private city tour that we have ever done.

2. Private Tour to Siena and Montalcino from Florence

Chianti Drivers
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5.0 based on 1 reviews

• Experience for your private group. If you are looking for beautiful sceneries, medieval city and excellent wines, this tour is for you. Explore the art, culture and medieval history of Italy in this private 9-hour Siena, Montalcino countryside tour from Florence. • Starting by visiting the marvelous Gothic town of Siena with its unique Campo square (where the famous Palio is run). • Then proceed towards Montalcino, a small medieval town situated on a hill dominated by the fourteenth-century fortress, in the countryside surrounding the town the famous "Brunello" wineyards. • Stop in one of the renowned wineries and enjoy visiting their cellar and tasting their great wines. • Don't miss a Lunch and wine tasting in an Winery or Farm. Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available for any of your needs.

Inclusions: Professional, English-speaking driver to lead you through the day, Private tour with luxury minivan, Free Wi-Fi on board, Bottled water, Hotel pickup and drop-off

Exclusions: Lunch, Wine tastings, Licensed city guide

Reviewed By Laurettab1974

We had a fab day! Our driver, Massimo was great! Very engaging, informative and made so enjoyable trip. Satisfied and exceeded our expectations Not only the tour through Tuscany was beautiful and the wine delicious, but above all Max made the whole experience unique! I recommend ChiantiDrivers to anyone! I highly recommend it.

3. 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.

4. PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

UniqueTuscany private Tours
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5.0 based on 27 reviews

• EXPERIENCE FOR YOUR PRIVATE GROUP • With this fascinating tour you will discover a unique part of Tuscany in a private day-trip from Florence. With an expert local driver/guide, immerse yourself in the renowned Chianti wine region and explore the cities of Siena and San Gimignano. You will tour historic landmarks such as Piazza del Campo in Siena, home to the annual Palio, and the medieval towers of San Gimignano. Add an optional, unforgettable lunch to savor traditional Tuscan wines and specialties in a local organic farm or winery! • 8/9-hr Full-Day private tour of Tuscany • Visit the medieval cities of Monteriggioni, San Gimignano and Siena • Hear live commentary of the wine cellars by your guide • Taste Craft Chianti Classico wine at a local vineyard • Pick-up and drop-off at your Hotel or at the address provided • Travel in a Mercedes-Benz minivan

Inclusions: Pick-up and drop-off at your selected hotel/location (in Downtown Florence), Private transportation by Mercedes-Benz MiniVan, Air-Conditioned, English-speaking licensed driver, Free time in Siena and San Gimignano, Unlimited cold mineral water , On-Board WiFi

Exclusions: Local guides in Siena and San Gimignano, Lunch in farm or winery available at an extra cost 25€pp to 50€pp, depending on option chosen, Entrance fees (Cathedral of Siena ia approx. 7€ pp.)

Reviewed By Gabriel S

This was our 2nd private tour that we did through Uniquetuscany (2017/2020). Our guide, Alessandro was very specific to the covid restrictions and offered us new masks during the day! He did a wonderful job explaining the history of the towns. Our highlight was the visit to Tuscany organic farm where we had our lunch with amazing view. We stopped at Siena, San Gimignano and Pisa. There was a lot of walking and moving from in and out of the minivan so make sure you wear comfortable shoes. I definitely recommend this tour while visiting Florence since you get a lot of history while on the minivan to each town. Just not enough time in all the towns but 10 hours is a long day! still worth the trip! Highly recommended..

5. Private daytrip to Siena & Chianti wine country, with wine tasting from Florence

Prestige Rent
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Private is just for you and your party, so the top in terms of flexibility, comfort, and privacy. Your knowledgeable English speaking driver, will discuss with you all the different options of the chosen itinerary, so you will be able to customize your day, to perfectly suit your needs and focus just on the attractions/activities you are interested in. Start your day with a relaxing visit of Greve in Chianti to learn about the country lifestyle, admire the beauties of the Chianti wine road and see postcard views, discover the secrets of the Chianti red wine, taste genuine products, and conclude your experience with a visit of Siena, Tuscany's second most important art city.

Inclusions: Private English-speaking driver, with fully equipped, Mercedes vehicle, Initial briefing with the driver with explanation of the options, to let you build your perfect day., Guided visit of a Tuscan winery followed by wine/olive oil tasting, Private transportation, Air-conditioned vehicle, All Fees and Taxes

Exclusions: Guided tour of Siena and entrace fees in Siena (if applicable), Lunch

Reviewed By JennaMarie63

Leo, our driver, was the absolute best! Funny, entertaining, and knowledgeable! An absolute blast! Highly recommend!

6. Private Tour: Secret Siena Walking Tour

Piazza del Campo, Il Campo, 53100 Siena SI, Italy Tuscan Escapes
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5.0 based on 20 reviews

Discover the older parts of Siena’s medieval centre and see hidden corners away from the crowded tourist areas, an exceptional itinerary to discover the quieter side of Siena.

Inclusions: Local guide, Private tour

Exclusions: Gratuities, Transportation to/from attractions

Reviewed By Paul D

We could tell within the first minute that our guide, Georgia, was going to give us a fantastic tour of Siena and we wern’t disappointed. Georgia brought the history of Siena to life with interesting stories, a sense of humour and an incredible depth of knowledge.

7. Private Tour: Siena, San Gimignano and Chianti Day Trip from Florence

Chianti Drivers
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4.9 based on 48 reviews

*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8/9-hour tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni and San Gimignano. See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano. • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs. * With agreements during the reservation we can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lover.

Inclusions: Hotel pickup and drop-off in Florence, Private luxury minivan, Bottled water, Onboard Wi-Fi (on request at reservation), Our drivers are all extremely familiar with Tuscany and with the main destinations in Italy. They will always share information, curiosities and traditions about the area of the sightseeing and they are available at any needs., Spanish-, Portuguese- or French-speaking driver upon request

Exclusions: Lunch in winery or farm. (to decide at the time of briefing in the morning with your driver), Guide city tour (you will find the complete tour with private guide in Siena on viator with this code 23322P50)

Reviewed By Laurettab1974

We had a fab day! Our driver, Massimo was great! Very engaging, informative and made so enjoyable trip. Satisfied and exceeded our expectations Not only the tour through Tuscany was beautiful and the wine delicious, but above all Max made the whole experience unique! I recommend ChiantiDrivers to anyone! I highly recommend it.

8. Siena Top 10 Pula Tour

Via Fusari, 30, 53100 Siena SI, Italy Polaroad
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4.8 based on 16 reviews

Our Polaguides will allow you to discover the most hidden places, but no less fascinating than Siena and instant photography will allow you to appreciate the beauty of the city from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be personalized, to browse whenever you want. Transform your visit to Siena into unique memories to share with the whole family, young and old, and with friends.

Inclusions: Polakit: 1 Polaguide + 1 instant camera (for hire) + 10 films + 1 map +1 backpack

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Reviewed By Stirlingfish

I can highly recommend Polaroad as a different way of discovering a city, for both occasional visitors and residents. We had a wonderful children's craft workshop there as the kids created their albums and a lovely memento of the experience... very educational on all levels, especially for digital natives.

9. Siena Cathedral: Private Tour

Piazza del Duomo, 53100 Siena SI, Italy Tour Guide Siena and Province
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4.8 based on 4 reviews

The Cathedral of Siena is an overwhelming monument that houses works of art from the Middle Ages to the contemporary period. Inside the church you can admire works by Donatello, Michelangelo, Bernini and discover their history with a professional guide and art historian.

Inclusions: Guided tour with an art historian, Private tour for up to 14 people

Exclusions: Entrance fees. Please note that the ticket price changes during the year and it's free for children under 11 years, Hotel pickup and drop-off

Reviewed By sd04walker

We enjoyed every second of the tour learning things that we would never have known without our local guide. Definitely recommend the experience!

10. Tuscan Experience - Private Shore Excursion to Chianti and Siena from Livorno

Driver in Italy

Italy makes largest contribution in the wine production over the world and is also famous for producing the finest quality of wine. Tuscany is worldwide known for producing the delicious Chianti wine and, of course, for its lovely medieval hilltop towns. With this Private Driving-Guided Shore Excursion you will become familiar with the best Chianti wine and will have a stroll in the most beautiful of those towns, Siena!

Inclusions: Private tour, Driver/guide at disposal full day, All taxes, fees, road tolls, fuel, Transport by air-conditioned minivan

Exclusions: Wine tasting to be paid on the spot (price starting from "free of charge" to 50 euro depending on the type of winery and tasting), Lunch, Gratuities

Reviewed By AtlantaLex

Used this service on three different visits for excursions and transfers to and from airports, train stations and cruise port. They escorted our whole family to Positano and Pompeii from Rome, and parents to perched villages and country lakes. We’ve recommended to our travel agent and close friends. Last visit we did Appian Way south of Rome, Church of Quo Vadis, and several lesser visited sites.

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