The Tuscany You Dreamed Of
In One Day

Imagine: walking around old towers, sipping a glass of red Chianti wine and living the traditions of Tuscany.

Don't waste your few days in Florence — live:

The experience everyone asks for.

But how much would a tour like this cost?

Instead, with us:

  • Mercedes van with a professional driver
  • Free Hotel pickup
  • Free time in San Gimignano before the crowds
  • Gelato tasting at Dondoli
  • Pecorino cheese masterclass
  • Wine tasting at a local winery
  • Taxes included
  • Insurance included
  • No hidden fees
  • Nothing to plan — we handle it all
Starting from €250 €199 per person
Request Availability →

Free cancellation 24h

What most agencies don't show in the listing

Crowded coach tour boarding — dozens of tourists

"This isn't what I expected."

A crowded bus with eighty strangers who don't even speak your language. It's common on big tours: the guide has to repeat every word in two or three languages.

Our way: tours run only by Mercedes van with a driver guide, English only.

Map: the long walk from the bus parking to the historic centre

The Hidden Walking Miles.

The legs burning, four to five miles extra by midday. Italian law keeps buses outside the old walls. That's why big operators ask you to meet outside the historical center, and then walk into each village from the parking lot on the outskirts.

Our way: a Mercedes van picks you up at your hotel door, for free. We drop you as close as the law allows — every time.

A narrow medieval street packed with touristsPHOTO NEEDEDDavid laughing with a small group at a piazza table, genuine candid, not posed — the anti-scripted-guide image'">

What you'll feel vs what you'll see.

Big operators do the same itinerary to maximize the stops in a day. The result: 20, 30, sometimes 50 coaches converge on San Gimignano at the same hour. A village this small becomes a queue of thousands of tourists.

For this reason we schedule off-peak — morning, before the buses arrive. Same place, different mood. They try to maximize what you see, we maximize what you feel.

David, born in Florence
Behind the day

After years in tourism, I built a different day.

"Ciao. I'm David. Born in Florence, raised in Tuscany."

I spent years working in Florence tourism — long enough to see the gap between what the brochure promised and what the traveler actually got. Too rushed. Too crowded. Too detached from the region itself.

So I left the system. I built a different kind of day — only for travelers who don't just want to see Tuscany and take 200 pictures, but for the ones who want to live it from the inside, to have experiences, to immerse themselves inside the traditions.

Two destinations. Eight guests. The Tuscany I call home — finally, the way it should be felt.

Travel with David →
What guests say
★★★★★
4.9 — verified reviews
on GetYourGuide & Tripadvisor
★★★★★
John 🇺🇸 United States
April 2026 · ✓ GetYourGuide

"Gabriele was an amazing host and guide!!! Very informative and able to answer whatever questions you threw at him. Excellent driver and extremely courteous. 5 star, you will not be disappointed!"

★★★★★
Jennifer 🇦🇺 Australia
May 31, 2026 · ✓ GetYourGuide

"Fantastic - David arrived right on time, and the drive up to San Gimignano was smooth and easy. We had a lovely cheese tasting experience in the town centre, and then headed to a winery called Tenuta Torciano. We had a gorgeous spread of local specialities, and the staff were lovely and very accommodating. We highly recommend for anyone looking for a day trip out of Florence!"

★★★★★
Camper696113
May 2026 · Family · ● Tripadvisor
Beautiful trip to the countryside!

We loved our experience going to San Gimignano! The pick up from our hotel was easy and the drive there was comfortable. It was great walking around the city centre and trying the amazing Pecorino cheeses. David, our fantastic guide, then took us to Tenuta Torciano winery for a Tuscan fine dining experience, including local wine tastings with the resident sommelier, Sylvia. We highly recommend this personalized experience for creating special memories of time spent in Tuscany.

★★★★★
Ashley 🇺🇸 United States
May 4, 2026 · ✓ GetYourGuide

"Our day trip with Gabriele was a true highlight of our trip to Italy! The day he planned for us was such a lovely opportunity to see more of Tuscany and our experience making and tasting pecorino was so wonderful. Gabriele's thoughtful care was the perfect energy for our family and we loved spending the day with him. We ended the day with a wine tasting in the hills - delicious food and an opportunity to learn about the wine of the region. Highly recommend!!"

★★★★★
Nicole A
Jun 2026 · Family · ● Tripadvisor
A must do day trip from Florence with excellent guide!

Gabriele was an excellent guide! He was super knowledgeable about the history of Tuscany and about the cheese, wine and gelato we tasted. He was also flexible, allowed for plenty of free time at each stop, and helped make the tour our own (we had previously booked tickets to climb the Duomo in Sienna and he modified the tour to accommodate!). We had private transportation and were picked up, and dropped off, right at our airb&b. San Gimignano and Sienna are absolute must see stops for anyone visiting Tuscany. My family and I had a wonderful day and I cannot recommend this excursion enough!

★★★★★
Brad 🇺🇸 United States
October 6, 2024 · ✓ GetYourGuide

"We had an amazing time. Gabriele was an awesome guide. He was helpful, patient and really took the time to explain things to us. We never felt rushed and he took us to places that made us feel very welcome. The tour of San Gimignano was incredible. Such a beautiful place. The view & the atmosphere was something that we'll never forget. The wine tasting was such a cool experience. The wine & the food were so good. We didn't want to leave. He even helped us out with a (hard to get) dinner reservation as he was dropping us off."

★★★★★
Cris Sydney, Australia
Jun 2026 · Friends · ● Tripadvisor
Great Company

Our guide was lovely, very knowledgeable and passionate about the local history. The cheese tasting was delicious (truffle cheese yum!) and the wine tasting with antipasto was equally divine. The wine sommelier was just as passionate. We had a private tasting room where we could look over the beautiful vineyards. Glad we booked a small tour (ours was private as no one else booked in for the day!) that had the advantage of being picked up direct from our accommodation! We booked the morning tour but I'd recommend booking the afternoon tour to have dinner included. Thanks again Gabriel/David for such a great day

★★★★★
Salma Alami 🇨🇦 Canada
February 24, 2026 · ✓ GetYourGuide

"One of the true highlights of my stay in Florence and Tuscany. I highly recommend this tour to anyone who loves poetic Chianti landscapes, great cheeses, flavored olive oils, and exceptional wine…"

★★★★★
Ash P
Jun 2026 · Family · ● Tripadvisor
Amazing experience!!

Gabriele is incredible! He is so knowledgeable and his pacing of the tour and cheese selections were amazing. We had an amazing time and would definitely rebook on another trip to Italy

★★★★★
Diane 🇺🇸 United States
April 13, 2026 · ✓ GetYourGuide

"It was a perfect tour of San Gimignano with some treats and a Cappuccino. We had free time there before we moved on the Tenuta Torciato winery. Both were excellent and so was our guide Gabriele."

★★★★★
Jeff 🇺🇸 United States
August 14, 2025 · ✓ GetYourGuide

"Very kind, knowledgeable guide, Gabrilele. Winery was fantastic with great wines. Highly recommend"

★★★★★
GetYourGuide traveler 🇨🇦 Canada
December 30, 2025 · ✓ GetYourGuide

"Driver was terrific. Wine tasting superb. Day was beyond expectations."

Questions

Got Questions? We Have Answers

Our tours are shared, but never crowded: maximum 8 guests, ever. It always feels like traveling with a few friends. Private options available on request.

No walking. We offer free pickup directly at your hotel — or convenient pickup areas in the city.

Transport in a Mercedes van, your English-speaking host with you all day, and the tastings listed in each tour. No hidden fees.

Tours run rain or shine — Tuscany is beautiful in every light. In severe weather, we'll reschedule or refund you.

Book the day

Message David.

Tell us your dates — popular weeks fill up first.

+39 352 077 8429 · info@thetuscanshow.com