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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.
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 both past and, to some extent, 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.
- Itinerary:SienaTuscan countrysideTraditional lunch (at additional cost)San Gimignano
- Included:English-speaking driverCar and driver at your disposalLicensed tour guide in Siena (optional)
- Wheelchair accessible:Yes. (Itinerary may differ).
- Meeting Point:At your hotel
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!
Wonderful Wine Tour My husband and I did the secret wine bar tour with Sara. She was an absolute delight—so easy to talk to, and very knowledgeable. She took us places we would... read moreMy husband and I did the secret wine bar tour with Sara. She was an absolute delight—so easy to talk to, and very knowledgeable. She took us places we would have never chosen on our own and they were all amazing!
My only warning is that you will be full by the end of this tour—which is a great thing! We weren’t sure how much food would be provided, so we made late dinner reservations that we ended up canceling because we had plenty to eat on the tour!!
I highly recommend this experience, and highly recommend requesting Sara as your guide! read less - 4/01/2022
A great evening with Marcos. I always wanted to know how to make the perfect pizza and gelato. Here, Marco the expert will show you how. It was a great participation event with lots... read moreI always wanted to know how to make the perfect pizza and gelato. Here, Marco the expert will show you how. It was a great participation event with lots of laughs, and we all got to sit down together afterwards to eat our creations. This is a great event for adults and children alike. Narco and his team are a credit to the company. read less - 12/05/2021
Exceeding Expectations in Unexpected Location This is an essential tour. After many trips to Rome this is an excursion we were excited to take. Our expectations were exceeded. Sara was great and made the tour... read moreThis is an essential tour. After many trips to Rome this is an excursion we were excited to take. Our expectations were exceeded. Sara was great and made the tour special. She has a great personality and is engaging. The chef, assistant, and team at Castel Gandolfo were all terrific to work with.
If there is one thing to do when visiting Rome after the major sites and time around the city, take this trip. read less - 12/03/2021
Geeking out at The Vatican Rosi was our guide for the experience and she was A+. Not just knowledgeable but also passionate and a great story teller. She was patient w questions and made the... read moreRosi was our guide for the experience and she was A+. Not just knowledgeable but also passionate and a great story teller. She was patient w questions and made the overall experience incredibly fun. read less - 11/30/2021
The 2 villas of Tivoli We did the Private tour of Villa D'Este and Villa Adriana in Tivoli. The driver picked us up from the hotel in Rome and drove to the Villa Adriana, where... read moreWe did the Private tour of Villa D'Este and Villa Adriana in Tivoli. The driver picked us up from the hotel in Rome and drove to the Villa Adriana, where our guide, Barbara, met us. Thoroughly versed in ancient history and art history, she was a lively and fascinating guide. Never exhausting or boring, always good company, Barbara clearly loves what she does, sharing her knowledge of Rome and environs and deepening the appreciation of discerning travelers who want to learn about what they see. She was a good sport, because it was a windy rainy day, not ideal for a long day outdoors! I would definitely hire her again. read less - 11/04/2021
Gracious, Knowledgeable, Experienced Walk Inside Rome has the best, most informed guides and they never disappoint!
From the first inquiry through the tour they are also the most gracious and accommodating. Our most... read moreWalk Inside Rome has the best, most informed guides and they never disappoint!
From the first inquiry through the tour they are also the most gracious and accommodating. Our most recent guide at the Vatican was TEO, knowledgeable, friendly, and someone who clearly loves the city of Rome. The owner of WIR, Marilena is hands on, and considers you a friend after the first tour! read less - 11/02/2021
Great Guide and Tour Very impressed and happy - From booking to the tour, everything was very smooth. I had some questions about the tour before booking - sent an email with responses prompt... read moreVery impressed and happy - From booking to the tour, everything was very smooth. I had some questions about the tour before booking - sent an email with responses prompt and the relevant information. We did the early morning Vatican Tour with Walks Inside Rome with our guide Barbara, who was amazing. Spending the extra money was worth the experience of WIR, in depth knowledge of the guide, early access to the Vatican and the path/route to see the highlights and relevant areas of the Vatican. Would highly recommend for anyone to book this tour, and would consider them for other tours next time in Rome! Thanks to the team at WIR and special shout out to Barbara who was so very considerate (my Mom was 89 years old and visiting the Vatican for the first time, making sure my Mom was at the front and able to see everything even though she was a tiny bit slower than everyone else! Grazie Mille! read less - 10/12/2021
Making Pizza & Gelato in Roma This was a fun, educational experience. I enjoy cooking, baking, etc so learning to make authentic Roman style pizza and a simple recipe for gelato is a skill I... read moreThis was a fun, educational experience. I enjoy cooking, baking, etc so learning to make authentic Roman style pizza and a simple recipe for gelato is a skill I can take home! Our chef/instructor, Marco, was enthusiastic and his experience shown through as he explained what and why following the recipes was important. The kitchen space was well equipped and the dining space magical. Next time we’re in Rome (yes we tossed coins in the Trevi Fountain) we will take another course from his organization. read less - 9/27/2021