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Why Choose It?
- Explore the seemingly cinmamon-sprinkled city of Siena.
- Dine on a traditional lunch in a local trattoria.
- Marvel at the perfectly preserved towers of San Gimignano.
Tour Description
This tour offers the perfect opportunity to explore two of Tuscany’s most stunning medieval towns. Admire the architecture spread throughout the seemingly cinnamon-sprinkled city of Siena before moving on to San Gimignano to explore the perfectly preserved town of the 14 towers.
After taking this private tour from Rome or Florence, you’ll feel you’ve fully explored the treasures of Tuscany’s lush and rolling countryside, experiencing the real side of rural Italy as you acquaint yourself with two of its most charming settlements.
Explore the winding streets of Siena
The first stop on your private Siena and San Gimignano tour is the medieval city of Siena, a fierce rival of Florence in the past and, to some extent, in the present. Siena was one of Italy’s leading city states throughout the Middle Ages, booming because of its still existent bank – Monte dei Paschi di Siena.
Wander the historic center’s contradas, the boroughs in which Siena is divided, and learn all the stories surrounding the famous Palio, a horseracing event dating back centuries and still held twice a year on July 2nd and August 16th in Siena’s Piazza del Campo.
Visit Siena’s Piazza del Campo, Duomo, and Church of San Francesco
Explore Siena’s Piazza del Campo, described by French philosopher Michel de Montaigne in the 16th century as the most beautiful in Italy, and marvel at its imposing bell-tower which looms out over the square.
Step inside the 13th-century Basilica of San Domenico, an incredible architectural achievement built on the slopes of the Sienese hillside. As well as housing an enviable collection of Tuscan artworks, the basilica is home to the relics of Saint Catherine of Siena – one of Italy’s two patron saints, the other being Saint Francis of Assisi.
Your final stop in Siena is the Duomo, whose beauty easily rivals that of its Florentine equivalent. Consecrated in 1215, it manifests one of the best examples of Italian Gothic and Romanesque architecture and boasts artworks by Bernini within.
Indulge in a traditional lunch at a local restaurant
For lunch, we will suggest one of Siena’s most reputed local trattorie, where you can linger over a long lunch accompanied by fine local wines, originating from the Sienese region or nearby Chianti or Val d’Orcia.
Meat is particularly popular across Tuscany, especially bistecca (beef steak) wild-boar based ragù. Yet the variety of culinary delights on offer caters to all tastes. Just make sure to try pici alla senese, the area’s beloved pasta, consisting of thick tubes of spaghetti coated in a mouthwatering meat sauce.
Continue on to San Gimignano, another jewel in Tuscany’s medieval crown
With your private driver you’ll then journey through the rolling hills of the Sienese countryside until you reach the towered town of San Gimignano. No town encapsulates medieval Tuscany like San Gimignano. Its state of perfect preservation owes not to its strength but to its weakness – for it was only the complete capitulation of its nobility in the 14th century (and an unfortunate spate of the Black Death) that saved the settlement from destruction.
The key to appreciating the enchanting town of San Gimignano is to take it slowly. Duck into the Collegiata to admire its breathtaking frescoes, indulge yourself with a gelato in the town square, and treat yourself to a glass of Vernaccia di San Gimignano wine – the product that’s made the town famous.
Having experienced the true Tuscany, your private driver will take you back through the rolling hills of the Italian hinterland to your accommodation in Rome or Florence.
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Itinerary:Siena HighlightsPiazza del CampoTuscan countrysideSan Gimignano highlights
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Included:English-speaking driverCar and driver at your disposalLicensed tour guide in Siena (upon request)
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Wheelchair accessible:Yes. (Itinerary may differ).
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Meeting Point:Hotel Lobby
excellent guides
Our guides are fluent in English and have a contagious passion for the inspiring cultural heritage of our Italian cities. Experts in their fields, they will immerse you in the hidden histories and intriguing lives of history's great protagonists. So much to see, so easy to miss out: with the help of our guides, visit the most absorbing sites and uncover the stories that have changed the world. Don't miss this fascinating journey!
- M2233BTrobertlTerrific Trastevere Food Tour with Luca! Luca took my wife and myself on a wonderful food tour through Trastevere. The things we saw and ate and learned were excellent. The best part was Luca's friendly nature.... read moreLuca took my wife and myself on a wonderful food tour through Trastevere. The things we saw and ate and learned were excellent. The best part was Luca's friendly nature. By the end of the evening we felt that we had spent a nice time with a new friend. read less - 10/03/2022
- Darren RA must do experience This cooking class was a highlight of our trip. We got to meet a young chef, Sara. She had us decide what to cook. Then we walked through... read moreThis cooking class was a highlight of our trip. We got to meet a young chef, Sara. She had us decide what to cook. Then we walked through the market to pick out some of the ingredients, the meats and such. Then we went back to their excellent small group kitchen. We had a wonderful time learning from Sara. She taught us to make ravioli and saltimbocca and tiramisu. It was fun and relaxed and extremely delicious. We thought the whole experience was splendid. 10 out of 10. read less - 9/26/2022
- genevieverbBest Food Tour We Took! My fiance and I capped off our first full day in Rome with this lovely food tour. Luca was friendly, excited, and knowledgeable. We got to try a ton of... read moreMy fiance and I capped off our first full day in Rome with this lovely food tour. Luca was friendly, excited, and knowledgeable. We got to try a ton of different food and even returned to one of the restaurants later in the week. The tour groups are kept small, so our group easily got to know each other throughout the tour. We were especially pleased with how accommodating it was: My fiance is a vegetarian and can be a bit of a picky eater, so he had low expectations going in and this ended up being his favorite activity all week! We actually had a couple of vegetarians in our group and there was always an equally hearty substitute whenever necessary. Super pleased with this experience and with Luca! Best part of our week! read less - 9/21/2022
- Emily WWorth every penny. What an evening! This was without a doubt the highlight of my trip. A great evening with plenty of incredible local food and drink and a really good way to meet and... read moreThis was without a doubt the highlight of my trip. A great evening with plenty of incredible local food and drink and a really good way to meet and get to know other travellers. The small group size made it much more personal and conversation flowed all evening! Sara (our guide) was absolutely amazing - so friendly and chatty, and so full of knowledge about the local food and Rome/Trastevere's history. She could not have been better.
I'll be coming back to Rome and will definitely be booking this again. Thank you so much, Sara, for making my first trip to Rome that much better! read less - 9/21/2022 - mrsmac0912Delicious food from fabulous foody Luca Boccia was PHENOMENAL!
His knowledge of Italian cuisine was exceptional, especially welcomed because it included more than just the well known dishes. He was funny and friendly, making our... read moreLuca Boccia was PHENOMENAL!
His knowledge of Italian cuisine was exceptional, especially welcomed because it included more than just the well known dishes. He was funny and friendly, making our time together unforgettable.
Most appreciated was his offer to remain a resource for the duration of our visit with DELICIOUS recommendations off the tourist path.
Well done Luca!!! read less - 9/11/2022 - uscimcA Must Do Tour of Sistine Chapel Amazing! This was my third time to the Vatican but this time I took my adult/teen children and wife and we used a tour guide. It was a... read moreAmazing! This was my third time to the Vatican but this time I took my adult/teen children and wife and we used a tour guide. It was a small group of 9. Just 2 families. She was great. She does this 4 days a week and all the guards knew her by name. If you want to see the Sistine Chapel, then you have to go early. We were one of the first to enter and with her connections basically did not wait on anything. We also entered a section in the Vatican Museums usually off limits to the public, a section with many animal statues and other mosaics. She gave us so much history and culture. My children said it was AP World History made real. You could tell she truly loved what she did. read less - 8/29/2022
- dvorahl2022Best tour ever. Martha was our guide. She is the best. They way she explained all , answered our questions give us all the information in every place all was wonderful. It was... read moreMartha was our guide. She is the best. They way she explained all , answered our questions give us all the information in every place all was wonderful. It was a very hot summer day and she always looks for ways to give us the information under the shade before we went into the sun. I highly recommend this company and Martha as well. It was very easy to make the reservation and pay. We took the private tour and was perfect. 3 hours that feel like Half hour . We didn’t do any limes to get into the places. Know that if you go by yourself or in other yours you could be up to 2 hours under the sun to get into the coliseum or forum. I highly recommend the private tour. read less - 8/05/2022
- michelleSheiowitzGreat Food Stroll with Luca We did the Trastevere Food Stroll with Luca B and he was great! Brought us to great authentic locations and provided his expert advice! We would highly recommend this tour... read moreWe did the Trastevere Food Stroll with Luca B and he was great! Brought us to great authentic locations and provided his expert advice! We would highly recommend this tour and Luca!! read less - 7/30/2022