Private tour in Siena Roberto C

Tour to Monteriggioni and San Gimignano, including Chianti wine tasting from Siena

4.9

(12) reviews

-
Hours icon 8 hours
Private transportation
Private tour for 1-2 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 8 hours
Private transportation
Private tour for 1-2 people
Your party size

1

View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later

Roberto C.

4.9

Guide rating

135

Reviews

Tours delivered

9 hrs

Avg. response time

Hi! I am Roberto, born and raised in Siena, a city in the heart of the Tuscan region of Italy. I am a highly dedicated and professional driver. I am enthusiastic and curious, inspired by my work and delighted when discovering hidden corners and new realities with my clients. Human interaction and intuitive insight are the secret to doing this job well. I pride myself on being sensitive and available, listening carefully to travellers' needs and paying the added attention it takes to make a travel and dining experience outstanding. My personal interests have served as training for the work I take great pleasure in doing. I have travelled across four continents and thoroughly enjoy meeting people and exchanging ideas. I am an avid reader and live by my father's creed: "Read! Ignorance is your worst enemy. If you don't know history, you don't know who you are. If you don't know geography, you don't know where you are". Last, but not least is my passion for eating and drinking…and well! I am a "buon gustaio" (literally translated: "good taster") and have extensive experience thanks to my mother's cooking. Meals in my family were the "family briefing"; that moment when excellent food and better wine brought us together for a peaceful rundown of our day. As for the future, I am dedicated to deepening my knowledge and expertise, in particular in the areas of food and wine. I have learned countless things from my experience so far and am looking forward to unearthing new hidden treasures together on a day tour soon! Certified Driver with professional experience as a driver guide. Fully Vaccinated Please note that I am not a licensed guide and will not be able to guide you inside of historical monuments and will not be able to accompany you on portions of the tour denoted by * - these parts of the tour will be un-guided.

Have a question or want to customize this tour? Message Roberto C.

Overview of your Siena tour

Travel back a thousand years and discover Monteriggioni, where you will take a walk along its walls and gaze out onto its surrounding, stunningly timeless countryside. Make a pilgrimage to postcard perfect San Gimignano, where 13 of its original 72 towers will envelope you and provide a striking and enchanting backdrop to your visit. I know my Tuscan food and wine. I will make sure that our lunch stop of typical Tuscan cuisine in a countryside setting will give you the best experience there is on offer and, of course, you will toast with a glass of Sangiovese or Chianti Classico. Take in the heart-stopping beauty of the Tuscan countryside that leads into the Chianti Classico wine country. Sample distinctive wines, exquisite extra-virgin olive oil, Vin Santo and Grappa, while expert guides reveal the secrets behind this world renowned wine making process. Stroll down a panoramic road in Castellina in Chianti, a Medieval, Florentine stronghold atop a hill, to where an authentic, handmade gelato tasting awaits

Recent Reviews

Himesh D.United States
October 2025

We could not have asked for a better tour guide than Roberto Cannavacciuolo. He was punctual, courteous, and well-versed in all things Tuscany. Roberto was able to get us reservations at two wineries, even though we made our travel and winery tour plans in the last minute. I highly recommend Roberto for anyone wanting to travel around Tuscany.

Rush S.United States
June 2025

This was our second day with Roberto where we started with a tour of Siena, where he was born. Siena is not to be missed. After a couple of hours we headed to Castellina in Chianti to visit a Chianti winery set in a lovely setting. After a leisure wine tasting and lunch, we headed off to San Gimigmano for some pictures of the towers. We were able to accomplish a lot in the two days we spent in Tuscany only because of Roberto's careful planning knowing he had two octogenarians as his clients. Can not praise Roberto too much for a stunning two day tour of Tuscany

Annette P.Italy
October 2024

Roberto Cannavacciuolo was responsive and cordial from my initial contact with him regarding a tailored itinerary, through the completion of several days with him throughout Tuscany. We enjoyed relaxing and insightful drives with him through the country as he drove us to different destinations. He is knowledgeable in the history of the cities, the country and the arts! He is very personable and enthusiastic, sharing his passion for Italy. He tailored our trips and information based on our interests. Roberto was always prompt and went beyond the typical transportation services, i.e. offering assistance in finding provisions (wine, meats, cheese of course) that we needed for our villa stay. Highly recommended.

Chevrel T.Isle of Man
October 2024

Roberto is a great guide! Our trip out and into the towns nearby was made all the more interesting with the help of his interest and knowledge about them, and of the routes, places and scenery around. Actually it was so interesting that we would have arranged more time with Roberto if we had had the time. Roberto took us to a beautiful location for lunch and took care of our every comfort. He is so kind and considerate.

Dave B.Canada
July 2022

Thank you Roberto. Tour was great and everyone in our group really enjoyed it

Dave B.Canada
July 2022

Roberto was great. Fantastic tour

Your Siena tour itinerary

- Monteriggioni castle* - San Gimignano* - Chianti scenic backroads - 1 Chianti Classico wine tasting - Gelato tasting (optional, extra charge) The parts of the itinerary denoted by * will be un-guided - you will be left to walk and explore by yourself for these portions of the tour. Contact me to plan your private, customized culinary-sightseeing tour in Tuscany together! This tour is priced and designed for 2 persons, I am able to accommodate larger groups at competitive prices, please contact me for a Customized Tour that will be priced and designed for your group.

Want to customize this tour?

Tell your guide which places matter to you, skip what doesn't, and tailor the experience for your group's needs. Not finding what you want? Message your guide to build something unique.

Transport details
Type: Private Transportation / Category: Minivan

Minivan with air conditioning, 1-8 comfortable seaters. Free Wi-Fi and refreshments on board.

What's included
Private Guide
Private Transportation
What's not included
Other: Personal expenses. - Lunch - Wine tastings - Eventual admission tickets
Food Drinks Snacks
Tastings
Meeting location

Tuscany, Tuscany, Italy

Airport: ,Cruise: ,ByGuide:

  • You can request a specific meeting location (for example, your hotel) during the checkout.
Other details
Tour categories
Food And Drink
Layover
Tour reference number
280747
Languages
Italian
English
Activity level
Minimal
Accessibility
Kid Friendly

Traveller reviews

4.9

FAQs

Who is this private tour in Siena best suited for?

This private tour is perfect for travellers who want to explore the Tuscan countryside with a focus on wine and food. It's ideal for those interested in history, as you'll visit Monteriggioni and San Gimignano, and for wine enthusiasts eager to taste Chianti Classico and other local wines. Families with children will find it suitable due to its kid-friendly nature, and it's also great for those who prefer minimal physical activity.

What should I bring or wear?

Can this private tour in Siena be customized to focus on what I want to see and skip places I've already visited?

How long is the tour, and can the start time or duration be adjusted?

Where does the tour start and end?

Is transportation included?

How much walking is involved, and is it suitable for kids, seniors, or travellers with mobility concerns?

What languages is this tour offered in?

What's included in this private tour, and what should I budget for separately?

AI-generated. Please confirm details with your guide

-
Hours icon 8 hours
Private transportation
Private tour for 1-2 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 8 hours
Private transportation
Private tour for 1-2 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
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