Location: Siena
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The 10 Best Historical & Heritage Tours in Siena, Tuscany
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 Day Trip from Rome to Siena and San Gimignano
Overall Ratings
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.
2. Piazza del Campo and Siena's Contrade, districts
Overall Ratings
5.0 based on 1 reviews
Piazza del Campo is the most important and beautiful square in Siena, where twice a year the Palio takes place. On this tour you will discover everything about our traditions and culture, still strong rooted in our daylife from the Middle Ages. Siena is divided into 17 districts called Contrade. To become a member people do a special baptism. You will discover the secrets of Piazza del Campo: what is the meaning of the word “Campo”? What type of events organize here the Sienese and dedicated to whom? Why is it considered the heart of the city? For the July Palio the Church of Santa Maria in Provenzano and for the August Palio the Cathedral dedicated to the Assumption of Mary are the protagonists, where the winner Contrada goes to celebrate. Every of the 17 districts have a unique museum, where prices won are kept: beautiful banners made of silk, called Palio, depicted by local and international artists. A visit to a Contrada museum is an opportunity to understand Siena.
Inclusions: Professional local guide, Guided visit of a Contrada Museum
Exclusions: Museum ticket not included (5 euros), until 13 years old the ticket for the musem is free
Reviewed By F7824SUoliviad
Very good guided tour. Our guide was very passionate about her city and its traditions. We really enjoyed it and learnt lot of things about Siena.
3. Small group Day Tour of Siena and San Gimignano from Florence! Tuscan Beauty!
Overall Ratings
5.0 based on 5 reviews
This is a wonderful way to explore two of the most scenic medieval towns in Italy. On board of a comfortable van you will experience the easiest way to visit those iconic towns of Tuscany in one day without stress, door to door service. The meeting point is in Florence centre, very easy to find.
Inclusions: Air-conditioned vehicle, Private transportation, The professional english speaking driver will explain you the attractions and traditions of towns
Exclusions: Lunch, Gratuities, Professional licensed guide (available on request with extra cost)
Reviewed By flobo5
My family and I first came into contact with Viaggi d'Ambra in July when I contacted them about a Chianti tour (see previous review) - we loved it so much, we didn't only book once again, but twice! My husband and I had the pleasure of a tour with Azzurra in the Montepulciano and Montalico regions in August - it was amazing! Both wineries were in lovely positions and the hosts were delightful. We also had time to explore the beautiful town of Pienza - not to be missed! After two fabulous tours, we booked to return to Tuscany in October. This time Christian took us on an amazing tour of northern Chianti. We visited the beautiful town of Greve and two fabulous wineries. Without Christian, we would never have found them and their wonderful wines! This year has all been a bit mad, but do book early for tours next year as Azzurra and Christian are fantastic people and know the area like no other. If you don't book, I can see myself taking tours with them daily - it really is such a fantastic experience and such a varied area! Grazie mille both of you!!!
4. Tuscany Experience in Pisa, Siena, San Gimignano & Chianti
Overall Ratings
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.
5. PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence
Overall Ratings
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..
6. Small Group Tour: Tuscany Wine Tour Siena and San Gimignano - Full Day Tour from Rome - Tasting and lunch included
Overall Ratings
4.9 based on 27 reviews
Enjoy travelling through Italy on a full-day journey from Rome in a Small Group max 12 people (only 6/7 per minivan), we'll through the hills of Chianti to visit the cities of San Gimignano and Siena. Explore the UNESCO-listed historic town of San Gimignano with its many Medieval towers. Stop for a wine tasting in the Chianti region, where you'll sample 10 types of wine and oil, and have lunch on the estate. Visit charming Siena, known worldwide for the famous Palio horse race.
Inclusions: Free transfer offered by Welcome Italy in air conditioning Minivan, Tour-guide escort, Wine tasting, taste local products and lunch, Hotel pickup and drop-off (central Rome only), Emergency number also operational via whatsapp
Exclusions: Gratuities, Tips
Reviewed By pilotjdk
had small group vacation planned for last October. cancelled due to Covid. Was offered voucher or refund. told them we needed refund due to not knowing if we would be travelling within a year. was told they would refund our money. Still waiting on a refund of 2084 and 1500 Euros.. that was over 7 months ago when it was cancelled. numerous emails. most of the time no response. Was promised refund when the person handling our group returned to work. nothing yet... Was really looking forward to a great vacation.
7. Siena Top 10 Pula Tour
Overall Ratings
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
Exclusions:
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.
8. Private Excursion to Siena, San Gimignano and Chianti Landscapes
Overall Ratings
4.8 based on 22 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 Florence.
Inclusions: Pick up and drop off at your Hotel if centrally located in Florence, Transport by deluxe air-conditioned vehicle with WIFI on board, English/Italian speaking driver, Local professional Guide at your side in Siena
Exclusions: Gratuities, Guide Service in San Gimignano, Entrance fees to the Cathedral in Siena, Everything not mentioned as Included
Reviewed By aakebe
Only 7 people and the tour was by Van. The driver guided us during the drive but no guide joined us at our stop in Castellina. Professional presentations at the wineries. Especially at Poggio Amorreli with Andrea where we were treated with Spumante, one white and two red Chianti and one supertuscan. We also got bread, cheese, salami with their own balsamic vinegar and olive oil. The driver called for a taxi upon arrival in Florence ????
9. Siena Cathedral: Private Tour
Overall Ratings
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. Small-Group Montepulciano and Pienza Day Trip from Siena
Overall Ratings
4.7 based on 78 reviews
Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO protected landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns, enjoy lunch and taste Pecorino cheese on a local farm! Numbers are limited to a maximum of 8 persons on this small-group tour, ensuring you'll receive personalized attention from your guide.
Inclusions: Driver/Guide, Transport by air-conditioned minivan (maximum 8 passengers), Cheese tasting, Lunch, Alcoholic Beverages
Exclusions: Hotel pickup and drop-off, 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.
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