Tuscany’s enchanting beauty beckons travelers to experience its picturesque landscapes and historic charm. This private day trip from Florence promises an unforgettable journey through the region’s renowned towns and vineyards. With a knowledgeable guide and comfortable transportation, visitors can enjoy the captivating sights, from the iconic Piazza del Campo in Siena to the medieval towers of San Gimignano. But the true highlight may lie in the opportunity to indulge in the renowned Chianti wine region, where the perfect blend of relaxation and exploration awaits.
Key Points

- Explore Siena, San Gimignano, and the Chianti wine region on a private day trip from Florence with a knowledgeable guide.
- Experience the UNESCO-listed Siena, including the famous Piazza del Campo and the impressive Cathedral.
- Visit San Gimignano, known for its medieval towers and picturesque Piazza del Duomo.
- Enjoy scenic views of vineyards and olive groves during the Chianti wine region portion of the tour.
- Transportation is provided in a comfortable, air-conditioned vehicle with hotel pickup and drop-off, bottled water, and free Wi-Fi.
Trip Overview and Pricing

The private day trip from Florence to Tuscany’s highlights of Siena, San Gimignano, and the Chianti wine region is priced from $858.49 per group (up to 2 participants) and lasts 8 hours.
Travelers can reserve their spot with no upfront payment and receive a full refund if they cancel up to 24 hours in advance.
Travelers can reserve their spot with no upfront payment and receive a full refund if they cancel up to 24 hours in advance.
This chauffeur-driven, air-conditioned tour includes hotel pickup and drop-off in Florence, bottled water, free Wi-Fi, and an expert guide.
While entrance fees to churches and museums are excluded, the trip promises an unforgettable experience exploring Tuscany’s UNESCO World Heritage sites and picturesque wine country.
Here are more experiences we've reviewed in Florence
Itinerary Highlights

As the private day trip from Florence explores Tuscany’s highlights, travelers will first visit the UNESCO World Heritage Site of Siena.
They’ll admire the Piazza del Campo, the Palazzo Pubblico, and the impressive Cathedral with its Italian Gothic architecture.
Next, the tour moves to San Gimignano, known for its medieval towers and the picturesque Piazza del Duomo.
The final stop is the Chianti wine region, where guests can savor the scenic views of vineyards and olive groves.
Throughout the journey, an expert guide provides insights and commentary to enrich the experience.
Transportation and Accessibility

For this day trip, travelers are chauffeured in an air-conditioned vehicle directly from their accommodation in Florence.
The transportation option is wheelchair accessible, ensuring all guests can comfortably explore the Tuscan countryside.
The trip includes:
-
Pickup from the hotel, allowing for a seamless start to the excursion.
-
Complimentary bottled water provided throughout the journey.
-
Free WiFi access in the vehicle, enabling guests to stay connected during the drive.
The convenient transportation and inclusive accessibility features make this Tuscany day trip an accessible and enjoyable experience for all.
Customer Experiences and Reviews
Travelers have consistently praised this Tuscany day trip with overwhelmingly positive reviews.
With an outstanding 5/5 rating based on 14 reviews, customers highlight the guide’s exceptional knowledge, friendliness, and passion. As one reviewer noted, the guide was "knowledgeable and considerate, providing an unforgettable lunch and wine tasting."
Another traveler described the experience as "exceeded expectations," praising the guide’s enthusiasm. Reviewers also commended the stunning views and beautiful sights along the way, calling the trip "outstanding" and "beautiful."
More Great Tours NearbyInclusions and Additional Information

The Tuscany day trip from Florence with a private chauffeur includes several key inclusions to enhance the overall experience.
The tour includes hotel pickup and drop-off, ensuring a seamless start and end to the day. Plus, bottled water and free WiFi are provided throughout the journey, keeping travelers hydrated and connected.
Lastly, a knowledgeable tour guide accompanies the group, sharing insights and historical context about the sites visited. While entrance fees for churches and museums are excluded, the inclusions ensure a comfortable and informative exploration of Siena, San Gimignano, and the Chianti wine region.
Here are more experiences we've reviewed in Florence
- Tuscany Day Trip From Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
- Cinque Terre Day Trip From Florence With Optional Hiking
- Best of Cinque Terre Day Trip From Florence
- Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti
- Private Day Trip Tuscany Landscape and Wine Tasting From Florence
- Private Day Trip to Cinque Terre and Pisa From Florence
Exploring Siena: A UNESCO World Heritage Site

Siena, a UNESCO World Heritage Site, stands as a captivating destination on the Tuscany day trip itinerary. Visitors can explore its medieval wonders, including the iconic Piazza del Campo, the stunning Palazzo Pubblico, and the Italian Gothic Cathedral.
| Siena Highlights | Description |
| — | — |
| Piazza del Campo | The shell-shaped town square, famous for the biannual Palio horse race |
| Palazzo Pubblico | The grand town hall with its distinctive torre (tower) |
| Cathedral | An architectural marvel featuring intricate marble façades and interiors |
| Palio Horse Race | A centuries-old tradition celebrated twice a year with vibrant pageantry |
| Sienese Gothic Architecture | The city’s distinctive architectural style blending Italian and French influences |
The private chauffeur-driven tour ensures a seamless and comfortable exploration of this captivating UNESCO site.
Discovering the Enchanting Town of San Gimignano

After exploring the captivating sights of Siena, the Tuscany day trip takes visitors to the enchanting town of San Gimignano.
Known for its iconic medieval towers, San Gimignano offers a unique glimpse into the past.
Visitors can:
-
Wander through the charming Piazza del Duomo, admiring the striking Romanesque-Gothic architecture.
-
Climb to the top of the tallest tower, Torre Grossa, for panoramic views of the town and the surrounding Tuscan countryside.
-
Indulge in the town’s renowned saffron-infused gelato and local Vernaccia white wine.
With its well-preserved historic center, San Gimignano enchants all who visit.
Indulging in the Chianti Wine Region
As the Tuscany day trip winds down, visitors are transported to the renowned Chianti wine region, a picturesque landscape dotted with vineyards and olive groves.
The tour guide leads the group through the scenic countryside, stopping at a family-owned winery. Guests are treated to a guided tasting of the region’s acclaimed Chianti wines, learning about the unique terroir and winemaking traditions.
The tour guide leads the group through the scenic Tuscan countryside, stopping at a family-owned winery for a guided tasting of acclaimed Chianti wines.
They savor the bold flavors and velvety textures, pairing the wines with a selection of local cheeses and cured meats.
The experience provides a fitting finale to the day’s exploration of Tuscany’s cultural and culinary delights.
The Sum Up

This Tuscany day trip from Florence offers a wonderful opportunity to take in the region’s enchanting beauty. Travelers can explore the UNESCO-listed city of Siena, marvel at the medieval towers of San Gimignano, and indulge in the renowned Chianti wine region, all while enjoying the convenience of private transportation and a knowledgeable guide. This excursion promises a seamless and memorable experience in the heart of Italy’s picturesque countryside.
You can check availability for your dates here:More Walking Tours in Florence
- Florence walking Tour: Music Headphones & Aperol Spritz
- Walking Tour: Florence Noir and Its Secrets
- Florence: Highlights Walking Tour with Expert Guide
- Florence Golden Hour Walk Tour & Piazzale Michelangelo
- Florence Crimes, Murders & Ghosts Walking Tour with Tastings
- Florence: 2.5 hour Audio Guided Walking Tour led by Host
More Tours in Florence
- Florence: Cathedral Duomo Tour with Local Guide
- Fiesole E-Bike Tour with Olive Oil Tasting or Pool & Chill
- Florence walking Tour: Music Headphones & Aperol Spritz
- Walking Tour: Florence Noir and Its Secrets
- Florence Old City Street Food Tour and Guided Sightseeing
- Florence Medici Bike Tour Cycle Through History and Power
More Tour Reviews in Florence
- Florence: Cathedral Duomo Tour with Local Guide
- Fiesole E-Bike Tour with Olive Oil Tasting or Pool & Chill
- Florence: Tuscan Cheese and Wine Tasting Experience
- Florence walking Tour: Music Headphones & Aperol Spritz
- Walking Tour: Florence Noir and Its Secrets
- Florence Old City Street Food Tour and Guided Sightseeing
Still browsing? Here are more Florence experiences we've covered recently
- What Are The Best 2-Hour Tours In Florence? Our Top 3 Picks
- Our Picks For The 13 Best Wine Tours In Florence
- The 12 Most Popular Workshops & Classes In Florence
- The 11 Best Dining Experiences In Florence
- 14 Best Tours In Florence
- Florence’s 10 Best Dinner Experiences (With Prices & Reviews)
- 14 Best Walking Tours In Florence (With Prices)
- Florence’s 3 Best Hiking And Trekking Tours
- 7 Must-Try Private Driver Services In Florence
- Florence’s 14 Top Food Tours
- 14 Of The Best Photography Experiences In Florence
- Our Picks For The 13 Best Pasta Experiences In Florence
