Private tour in Florence Roberto C

Day trip to San Gimignano, Monteriggioni and Chianti Classico from Florence

4.8

(25) 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 Last-Minute 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 Last-Minute Cancellation
Book with a depositSecure your tour today and pay your balance later

Roberto C.

4.9

Guide rating

136

Reviews

Tours delivered

11 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 Florence tour

Travel back a thousand years and discover Monteriggioni, 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 you!

Recent Reviews

Lon Z.United States
4 days ago

Roberto provided an incredible day in Tuscany! He was easy to book and communicate with and provided history of the area with stops and time to explore beautiful old towns. The wine tasting and lunch was the highlight. We would book him again and highly recommend him.

Rick L.United States
February 2026

Well-organized and flexible Chianti experience with excellent winery visits Roberto provided a very smooth and enjoyable day exploring the Chianti region. He was proactive in advance, and the logistics were excellent throughout. Pickup was seamless, the vehicle was comfortable, and the entire day was easy and well paced. He was also very accommodating and flexible to our interests. He took us to a small medieval hilltop village that we would not have discovered on our own, and he gladly stopped at a Franciscan church and monastery when we expressed interest in visiting. Those spontaneous moments added a lot to the experience. He arranged visits to two outstanding wineries, both of which were highlights. One was a small, family-run vineyard dating back to 1620 with unique high-elevation terroir, and the other was a slightly larger producer with a wider range of wines. Both were excellent, and the hospitality and food were exceptional. Roberto’s strengths are in organizing a comfortable, flexible day and providing access to excellent wineries and locations. He ensured that everything ran smoothly and created a relaxed and enjoyable experience in the Chianti countryside.

Diane S.Australia
January 2026

Excellent day trip to the Tuscan Hills. We visited 3 Medieval towns, San Gimignano, Monteriggioni and Castellina in Chianti. Coming in the middle of winter the crowds were sparse but many things were not open. Our visit to a private winery for tastings and a home made lunch was superb and added that value added touch to the day. It was relaxing and very enjoyable. Roberto was friendly, knowledgeable and a very safe driver.

Tina K.United States
October 2025

I had a fantastic experience on our wine tour in Tuscany! Roberto was well-organized from start to finish—the communication was excellent and timely, so we always knew what to expect. The highlight was definitely the wine tasting at a beautiful local winery. The staff was knowledgeable and welcoming, and the wines we sampled were outstanding. I highly recommend this tour for anyone looking to explore the Tuscan countryside and enjoy some truly exceptional wines!

Walker H.United States
October 2025

Wonderful experience with Roberto. His passion for his country shines through. We love his flexibiity in meeting our wishes in what we want to experience. Our afternoon at a winery in Tuscany was amazing. He is a gem!

Stephen C.United States
June 2025

We were able to customize our tour and incorporate excellent suggestions from Roberto to make this excursion into Tuscany unique and memorable! Roberto's knowledge of the history of the sites we saw added significantly to our understanding of the region. Thanks Roberto!

Your Florence tour itinerary

- Monteriggioni castle* - San Gimignano* - Monteriggioni* - Castellina in Chianti* - Chianti scenic backroads - Winery and wine tasting - Gelato tasting 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 passengers. 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

Florence, Tuscany, Italy

Airport: ,Cruise: ,ByGuide:

  • You can request a specific meeting location (for example, your hotel) during the checkout.
Other details
Tour categories
Nature Wildlife And Safaris
Day Trip
City Highlights
Layover
Tour reference number
280753
Languages
Italian
English
Activity level
Minimal
Accessibility
Kid Friendly

Traveller reviews

4.8

FAQs

Who is this private tour in Florence best suited for?

This private tour is perfect for travellers who want an exclusive, personalized experience exploring Tuscany's beautiful countryside. It's ideal for those interested in history, wine, and culinary delights, as well as families with kids, given its minimal activity level and kid-friendly nature. If you're looking to connect with a local expert like Roberto C. for deeper insights into the region, this tour is a great choice.

What should I bring or wear?

Can this private tour in Florence 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 Last-Minute 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 Last-Minute Cancellation
Book with a depositSecure your tour today and pay your balance later
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