10 Tours in Siena That You Shouldn't Miss

October 24, 2021 Milan Banda

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. Tuscany Experience in Pisa, Siena, San Gimignano & Chianti

Sightseeing Experience Visitor Center (tourist assistant), Stazione, atrio biglietterie, Piazza della Stazione, n.1, 50123 Firenze FI, Italy Sightseeing Experience
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5.0 based on 1 reviews

Your day starts in the morning with a free tour of Pisa, where you will have time to admire the magnificent cathedral, the baptistery, the monumental cemetery and the famous Leaning tower of Pisa. Afterwards, we'll move in a Typical Winery in the Chianti Hills, on the slopes of San Gimignano, where we will enjoy a typical Tuscan lunch with a good local wine tasting. After lunch you discover, San Gimignano: the Medieval Mahanattan, where you can explore the maze of cobbled streets, small squares and many local craft stores. Our exciting day continues with a panoramic view of the true Chianti countryside before arriving in Siena, where our professional guide will let you discover the most important squares, from Piazza del Campo to the Cathedral passing through the most beautiful ‘Contrade’ that characterize this city. At the end of the guided tour, you will have free time to enjoy a cup of coffee or the Pan Forte (the typical local cake) and have some shopping in typical local shops.

Inclusions: Transfer with equipped GT bus with conditioned air , Expert multilingual excort ( not for Private Transfer Only ) , Free time in Pisa and San Gimignano , Guided Tour in Siena ( not for Low Cost, Private Transfer Only and Private & Lunch ) + Free Time , Lunch in a typical winery in the Chianti area ( not for Private Transfer Only ), Tasting of 3 Wines and Olive Oil ( not for Private Transfer Only ) , Cantuccini tasting (typical Tuscan biscuits) ( not for Private Transfer Only ) , Wi-Fi on board the bus

Exclusions: Pick up service ( For Private Tour, you can ask for it, if the hotel is in city centre )

Reviewed By RobbieFPB

Wish we had read the reviews before booking. Palermo is quite small and most the main sights are very central, so you don’t really need a bus tour. However, even if you are not keen on walking, the bus tour will be of little use, as the advertised ‘hop on, hop off, every 20 minutes’ is simply untrue. The bus only arrives every 90 minutes (we lunched in a restaurant next to the stop we alighted from and that was the time gap). In addition, there is no access to a live map for bus arrivals, so you have no idea when the next bus will arrive. In a nutshell, it’s a rip off.

2. 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..

3. Small-Group Chianti Wine-Tasting and Castles Trip from Siena

Piazza San Domenico, Piazza S. Domenico, 53100 Siena SI, Italy Tuscan Escapes
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4.9 based on 35 reviews

Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian castles are a must-see for any visitor to the region. With your expert guide, visit Castello di Brolio, renowned as the birthplace of Chianti wine. Sample the esteemed Chianti Classico wine, enjoy an authentic Italian lunch at a Tuscan wine estate and tour the cellars to learn about the passion behind this traditional wine directly from the producer. Enjoy some of the region’s best wines directly at the winery. Numbers are limited to eight people on your small-group trip, ensuring you'll receive personalized attention from your guide.

Inclusions: Professional guide, Lunch, Wine tasting, Air-conditioned vehicle

Exclusions: Gratuities, Hotel pickup and drop-off, Entrance to Castello di Brolio

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.

4. Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Piazza San Domenico, Piazza S. Domenico, 53100 Siena SI, Italy Tuscan Escapes
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4.9 based on 310 reviews

Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover the cellars where these incredible wines age, meet the local producers, and learn about the passion that goes into making this wine. Enjoy a traditional Tuscan lunch at a winery and spend time relaxing at your leisure in the village of Montalcino before exploring the mystical abbey of Sant'Antimo. Visit a total of three wineries in the region, tasting unique creations at each one. Numbers are limited to eight people on this small-group tour, ensuring you'll receive personalized attention from your guide.

Inclusions: Local Guide, at family run winery, Visit to wine cellars and wine tasting, Air-conditioned vehicle

Exclusions: Gratuities, Hotel pickup and drop-off

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.

5. 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.

6. 8- Days Best of Italy Trip from Rome

Carrani Tours
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4.9 based on 7 reviews

Visit Italy’s top destinations — Rome, Assisi, Florence, Bologna, Padua, Venice and Tuscany Wine Region (Montepulciano) — on this 8-day tour from Rome. With a mix of free time and guided portions, this is an ideal introduction to the regions of Umbria, Tuscany and Veneto. Check out the historical cities of Assisi, Siena and Montepulciano; soak up Florence’s wealth of art and architecture; and then continue to Padua and Bologna before arriving in Venice, home to sights like St Mark's Basilica and then continuing to the final destination Rome with the visit of the Vatican Museums and St. Peter's Basilica. Three nights of accommodation in Rome, two nights in Florence and Venice and round-trip transport by coach are included. Your hotels in each city are centrally located for maximum convenience, and 4-star hotel for your time in Venice,Rome and Florence.

Inclusions: Breakfast, Breakfast, Dinner, Breakfast, Breakfast, Dinner, Breakfast, Breakfast, Lunch, Breakfast, Lunch, Air-conditioned vehicle, Onboard WiFi, Professional guide, Seven nights of hotel accommodation, 4 Meals as per itinerary, 7 breakfast, Transfer from Rome Airport to Rome hotel and vice-versa, Breakfast

Exclusions: Gratuities, Food and drinks, unless specified, City tax

Reviewed By ESKILD-SUSANNE-DK

We had a really good tour around The Vatican including all the museums. Our guide Rita gave us a very interesting and informative tour. It was at times very difficult having a face mask on all the time but she was able to give us the best tour even with a mask. Thank you very much, Rita Eskild og Susanne

7. Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

Tours of Tuscany
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4.9 based on 27 reviews

This full-day tour will bring you a taste of the complex, full-bodied Brunello reds that make this region every wine lover’s dream. We will pick you up at your hotel & take you to some of the lesser-known vineyards with high-quality wines. After your first tasting, take some time to explore the hilltop town of Montalcino, where we will visit a second Brunello winery. Then we will continue to Pienza, a UNESCO World Heritage Site & a unique example of the ideal city according to Renaissance architecture. Then one last stop in the small town of Montepulciano, where you can taste the exquisite Nobile di Montepulciano wine & meet the winemakers that make the magic happen. Enjoy a special lunch featuring local specialities. Pick-up & Drop-off at your accommodation 3 wine tastings at boutique wine cellars Lunch with wine pairings & local specialities Visit Pienza & Montepulciano Small group: limited to 8 guests Don’t drive while you wine & dine! Let us take care of everything.

Inclusions: 3 Winery tour and tasting, Pairing lunch at a historic winery, Bottled water, Air-conditioned vehicle, WiFi on board

Exclusions: Gratuities

Reviewed By Sogufa

Amazing experience. Kindness and professionalism at the same time. Well organised and safe in all aspects.

8. Tuscan Cooking Class in Central Siena

Scuola di Cucina di Lella di Lella Cesari Ciampoli snc, Via Fontebranda, 69, 53100 Siena SI, Italy Scuola di Cucina di Lella
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4.8 based on 50 reviews

Tuscan Cooking Class. Cooking Class of traditional Tuscan meal from starter to dessert including a fresh home-made pasta at the end of the lesson dinner with all prepared accompanied with Chianti Wine. The maximum number of customers per lesson 15 people. The school has applied all the legal regulations for sanitizing from Coronavirus. The school provides customers with everything necessary established by current safety standards (masks, gels, etc.). Customers actively participate in the preparation of recipes Use of seasonal and local ingredients Vegetarian and gluten-free menus available Customers will learn all the secrets of Italian and Tuscan cuisine and will receive handouts with the prepared recipes Private lessons on request in the morning

Inclusions: 4 - hour Tuscan cooking class in Siena, Prepare from starter to dessert, fresh home-made pasta., After the lesson dinner with prepared meals accompanied by an excellent chianti wine, Small-group cooking class with a maximum of 15 people, The Lella's cooking school is large and well equipped

Exclusions: Transportation to/from attractions

Reviewed By Amanda R

This experience was amazing! Lella was amazing as well as her sous chef and her interpreter Julie. You can tell that Lella is incredibly passionate about cooking because it shows in her food as well as her teaching. We learned how to make homemade spaghetti by hand, soup, pasta sauce (the best!) pork lion with potatoes and panna cotta! Everything was honestly delicious! The class was also very fun! I highly recommend!!

9. Tuscany in One Day Sightseeing Tour from Florence

Piazza della Stazione, 50123 Firenze FI, Italy Walkabout Florence Tours
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4.8 based on 8,621 reviews

Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day to spare, see the best Tuscany has to offer on this full-day guided coach trip from Florence.

Inclusions: Air-conditioned vehicle, Professional guide, Detailed maps of all destinations visited, 3-course lunch at a wine estate (not included in the tour option without lunch), Wine tasting (not included in the tour option without lunch), Free time to explore the towns at your own pace

Exclusions: Gratuities, Hotel pickup and drop-off, Food and drinks, unless specified

Reviewed By katiegN3709NB

Christian helped make our Florence experience memorable! My husband and I traveled throughout Italy with our two young children ( 8 and 5 years old) and they were so excited for their Fiat tour. They were the only kids on the tour but Christian made sure it fun and educational for them. The whole group was inviting and it was great to get to meet people from all around the world! My kids can not wait to travel more and still talk about how awesome the tour was. I highly recommend this tour with or without kids. We were taken to scenic views throughout Tuscany and even had to maneuver through the streets of Florence in a super fun classic Fiat. Everywhere we drove people would stop and wave because of the group of Fiats brought joy to everyone! This was the best tour we took in Italy and when we come back for a visit we are definitely doing it again! (Our tour was pre-covid)

10. Siena and San Gimignano: Small-Group Tour with Lunch from Florence

Piazzale Montelungo, Firenze FI, Italy Prestige Rent
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4.8 based on 243 reviews

Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable and relaxed way with more personalized attention of a small group. Depart from Florence, see the highlights of Siena through the eyes of a licensed guide, admire the marvelous Tuscan landscape, taste genuine Tuscan food paired with great wines, and finish your day relaxing in the hill top village of San Gimignano.

Inclusions: Small group day trip to Siena and San Gimignano from Florence, Professional and informative English speaking guide + driver, Roundtrip transportation by air-conditioned minibus or minivan (Mercedes or similar) with free wi-fi, Guided walking tour of Siena highlights + free time in Siena, Entrance fees to visit the interiors of the Siena Cathedral (if option reserved), Lunch at a Tuscan winery, paired with their excellent red wines, Free time in San Gimignano

Exclusions: Hotel pickup and drop-off, Gratuities

Reviewed By Alli S

We did a private wine country tour with Francesco in October 2019 (it has taken me entirely too long to write this review). We had a great time with Francesco. He is so personable and was so much fun to spend the day with. Ask him to tell you the story of why there are black roosters on Chianti Classico wine bottles. Francesco is very professional, was able to accommodate a change in plans based on our preferences, and delivered top-notch service throughout the day. If (when) we go back to Florence, we will be giving Francesco a call!

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