Florence
9 hours
1–6

Highlights

  • Discover Tuscany’s medieval treasures in one seamless day – Explore Siena’s Gothic cathedral, San Gimignano’s towers & Chianti’s rolling vineyards.
  • Experience Siena’s rich history & traditions – Visit the UNESCO-listed Piazza del Campo, home to the legendary Palio horse race, and more with a local guide.
  • Tour a historic family-run vineyard – Visit a renowned Tuscan winery, sample local varietals, and learn the secrets of world-famous Chianti.
  • Savor a farm-to-table Tuscan lunch – Enjoy a homemade, locally sourced meal, paired with the winery’s finest Chianti wines.
  • Travel in comfort with a private driver & expert Walks of Italy guide – Sit back, relax & enjoy a stress-free Tuscany experience with personalized insights.

Tour description

Discover Three Stunning Destinations on a Perfectly Planned Tuscany Day Trip

Rolling hills, medieval towns, and world-class wines—this is the Tuscany of your dreams. On this Private Tuscany Day Trip from Florence, travel in comfort with a dedicated English-speaking driver, exploring Siena, San Gimignano, and the Chianti wine region on an all-inclusive Tuscan adventure.

With a farm-to-table lunch at a family-run vineyard, a walking tour of Siena with a local guide, and a seamless itinerary designed for maximum relaxation and discovery, this private tour is the best way to experience Tuscany in a single day.

Explore Siena’s History, Art & Medieval Traditions

Your day begins with Siena, one of Tuscany’s most breathtaking medieval cities. Once you arrive, you'll meet your private guide and discover:

  • Piazza del Campo – The heart of Siena, home to the Palio horse race and the stunning Mangia Tower.
  • Siena Cathedral (Optional Visit) – Admire the intricate black-and-white marble façade and breathtaking interiors.
  • Local Traditions & Historic Streets – Stroll through centuries-old alleyways and discover the unique culture of Siena’s Contrade (neighborhoods).

Enjoy a Farmhouse Lunch & Wine Tasting in Chianti

No Tuscany tour is complete without exceptional food & wine. After saying goodbye to your local guide in Siena, you’ll hop back in the car and head to a family-run Chianti vineyard, where you’ll enjoy:

  • A guided tour of the winery & vineyard – Learn the secrets behind Chianti Classico & Super Tuscan wines.
  • A homemade, farm-to-table lunch – Savor a seasonally inspired Tuscan meal made with fresh local ingredients, paired with the vineyard’s finest wines.
  • Tuscan Hospitality at Its Finest – Experience the warmth of true Italian countryside living with local winemakers.

Step Into a Fairytale in San Gimignano

With full bellies, you’ll continue to San Gimignano, one of Tuscany’s most famous hilltop villages. Here, you’ll have free time to explore on your own. These are some ideas of how to spend the perfect afternoon:

  • Wander its medieval streets – Admire the town’s 14 historic towers and breathtaking panoramic views.
  • Shop local artisan goods – Browse handmade ceramics, olive oils, and wines unique to this region.
  • Taste Italy’s best gelato – Visit Gelateria Dondoli, a world-famous gelateria known for its award-winning flavors.

Why Choose a Private Tuscany Tour?

This private tour follows a carefully planned route, ensuring you experience Tuscany’s most beautiful towns and best wine regions in one effortless day. With a dedicated guide in Siena, private driver, and all logistics handled for you, it’s the most relaxing, personal, and immersive way to see Tuscany from Florence.

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Total guest reviews: 224

Verified rating
4.9/5
based on 0 Walks' customer ratings
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Latest guest reviews

Lisa-Patrizia

Guter Zeitplan (Einschränkung siehe unten), nette Guide, zwei sehr gute und nette Fahrer. Gruppengröße okay. Sehr enttäuschend war leider die Weinverkostung. Erinnerte mehr an eine Kaffeefahrt, ständig wurde darauf hingewiesen, was man im Bestellzettel ankreuzen soll. Olivenöl, Balsamico und Wein waren durchschnittlich, die Pasta auch. Es gab keine Weinkellerbesichtigung, oder Blick in die Weinberge oder irgendetwas anderes, was man nicht auch in einem durchschnittlichen Restaurant hätte haben können. Auf dem Rückweg ist die traumhafte toskanische Landschaft an uns vorbeigerauscht, ohne jegliche Möglichkeit, sie zu genießen. Ja, wir waren alle platt, aber ein kurzer Stopp an einem Aussichtspunkt hätte noch sehr gut in den Zeitplan passen können. Insgesamt war das Preis-Leistungs-Verhältnis für einen "ultimativen Toscana-Tagesausflug" nicht angemessen. Leider waren wir etwas enttäuscht.

GetYourGuide customer Oct 24, 2026
Sharon

This tour was a great way to get out of Florence for a day and experience more of what the Tuscan region has to offer. Anna was our guide. She was personable, knowledgeable, and spoke great English. There were only eight of us on this tour, and we rode in two separate comfortable vans with very capable drivers (Marco was ours). Stops in both San Gimignano and Sienna were lovely, with plenty of time to explore on our own after Anna got us started and gave us some helpful background information. The lunch at the winery was very nice. Not the beautiful view of rolling vineyards that I was expecting, although we did see that as part of our drive as well as a bit from the towns. Lunch included several wines and three courses in a cute little refurbished barn in a quiet part of the country, which was so peaceful after the hubbub of Florence. I highly recommend this tour as a great way to see Tuscany outside of the city.

Viator customer Oct 23, 2026
Brody

What a highlight of our trip!

GetYourGuide customer Oct 21, 2026
Carolyn

I had a wonderful time on this day trip in Tuscany! Ezgi was our guide and she was amazing. I traveled with my two sisters, all of us retirement aged. Ezgi was so personable and made sure that each member of the tour was looked out for. She was knowledgeable about the areas and the wines and wine regions. Plus, she had great information about the best ways to access certain things and what might suit our specific needs. We really enjoyed visiting with her and appreciated all she did for us. Our driver was great and I appreciated how hard he had to work to get us to all the places safely. The winery we visited was so charming and we had a great education about the wines they produced. We tasted several and were fed some amazing food as we did our tasting. It was a chance to relax and enjoy the tastes of Tuscany. I would recommend this trip to anyone, young or old!

Viator customer Oct 20, 2026
Joanne

itnery was great. longer in San gimignano would have been good. winary hostess was extremely difficult to understand. overall a great experience

GetYourGuide customer Oct 16, 2026
Eric

Lorenzo was a fantastic guide. They were engaging, enthusiastic, and authentically Italian. We had a great time at the vineyard and thoroughly enjoyed the wine tastings and lunch. I’d recommend this tour for those who want to see the Tuscan countryside

GetYourGuide customer Oct 09, 2026

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