When travelers think about Tuscany, images of rolling hills and charming villages come to mind. A private tour from Florence to Siena and San Gimignano offers just that, plus a taste of the region’s famous wines. Visitors can enjoy Siena’s medieval charm and enjoy San Gimignano’s iconic towers. But the experience doesn’t stop there; there’s also a delightful wine tasting waiting to be discovered. What other surprises does this tour hold?
Key Points

- Enjoy a private tour from Florence to Siena and San Gimignano, tailored to your interests for a personalized experience.
- Explore Siena’s medieval architecture and rich history, including the iconic Piazza del Duomo.
- Visit San Gimignano, famous for its medieval towers and delightful gelato, while wandering its charming cobblestone paths.
- Experience a guided wine tasting that highlights Tuscany’s renowned wines, with insights into local winemaking traditions.
- Travel comfortably in a luxurious air-conditioned minivan, with a small group size for enhanced interaction and convenience.
Explore the Rich History of Siena

Siena, a gem in Tuscany, boasts a history that’s as rich as its famous wines. This medieval city’s roots stretch back to the Etruscans, but it really flourished during the Middle Ages.
Its stunning architecture, like the majestic Piazza del Duomo, tells tales of art and politics, while the narrow, winding streets echo centuries of vibrant culture.
Visitors can almost feel the excitement of the Palio, the famous horse race that brings the community together.
With every corner turned, Siena reveals another piece of its captivating past, making it a must-visit for anyone intrigued by history and charm.
Hungry for more Florence flavors? We've covered these other food and drink spots
Discover the Charm of San Gimignano

Nestled on a hilltop, San Gimignano captivates visitors with its stunning medieval towers and charming streets that seem frozen in time.
This picturesque village, often dubbed the "Manhattan of Tuscany," boasts 14 towering structures that tell stories of its rich past.
As you wander through cobblestone paths, you’ll discover quaint shops, vibrant local art, and, of course, some of the best gelato around.
The views from the hilltop are breathtaking, offering a perfect backdrop for memorable photos.
San Gimignano’s unique blend of history, art, and culture makes it a must-visit gem in the heart of Tuscany.
Indulge in Authentic Tuscan Cuisine

While exploring the enchanting landscapes of Tuscany, food lovers find themselves in a culinary paradise, where authentic Tuscan cuisine reigns supreme.
Imagine sinking your teeth into homemade pasta, drizzled with rich, savory sauces that burst with flavor. At a traditional trattoria in Monteriggioni, locals whip up dishes using fresh, local ingredients, ensuring every bite tells a story.
Don’t forget the iconic ribollita, a hearty soup that warms the soul.
And for dessert, the gelato in San Gimignano is simply legendary, creamy and bursting with natural flavors.
It’s a food journey that’s sure to leave taste buds dancing with joy!
Experience a Guided Wine Tasting

Tuscany boasts some of the world’s finest wines, and a guided wine tasting here is an experience not to be missed.
Guests dive into the rich traditions of winemaking while sampling exquisite local varieties. Knowledgeable guides share fascinating stories about the vineyards and the unique terroir that gives each wine its character.
Participants savor the flavors, learning to distinguish between the bold reds and crisp whites that define this region.
It’s not just about sipping wine; it’s about connecting with the culture and passion behind each bottle.
Cheers to unforgettable moments and delightful discoveries in Tuscany’s vibrant wine scene!
Enjoy Scenic Views of the Tuscan Countryside

The rolling hills of the Tuscan countryside create a breathtaking backdrop that captivates travelers at every turn. Vibrant vineyards, olive groves, and charming medieval towns dot the landscape, inviting awe and exploration.
As the luxury minivan glides along winding roads, travelers can’t help but snap photos of sunflower fields and rustic farmhouses. Each viewpoint offers a new perspective, blending tranquility with the rich history of the region.
Whether it’s a fleeting glance or a lingering moment, the scenery leaves a lasting impression. It’s this stunning panorama that truly makes the journey from Florence unforgettable.
Ready for another glass? Here are more wine experiences we've reviewed in Florence
- Small-Group Wine Tasting Experience in the Tuscan Countryside
- Tuscany Day Trip From Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
- Full Day Tour to Val Dorcia and Gladiators Fields With Wines
- Wine Safaris: off Road Tuscany Wine Tours and Lunch From Florence
- Tuscany Bike Tours Through the Chianti Hills With Wine Tasting
- Florence Sunset Food & Wine Tour With Eating Europe
Private Tour Benefits and Small Group Experience

When travelers embark on a private tour, they unlock a world of personalized experiences that larger groups simply can’t offer.
The small-group format, with a maximum of just eight people, fosters genuine connections and allows for deeper interactions with the guide. This intimate setting means everyone can ask questions, share stories, and soak in the sights at their own pace.
Plus, the tailored itineraries cater to specific interests, ensuring no one misses their must-see spots. Whether it’s savoring local cuisine or enjoying a leisurely wine tasting, a private tour makes every moment feel special and unforgettable.
Convenient Meeting and Pickup Information

For those eager to explore the beauty of Siena and San Gimignano, the meeting and pickup process couldn’t be easier. Here’s what you need to know:
-
Location: Meet at Cantinetta Antinori, Piazza degli Antinori in Florence.
-
Time: The adventure kicks off at 8:00 AM sharp.
-
Comfort: Enjoy a luxurious air-conditioned minivan for the ride.
-
Return: You’ll end back at the same spot, making it super convenient.
With this simple setup, travelers can dive straight into the Tuscan charm without any hassle.
It’s all about ease and enjoyment!
Customer Testimonials and Experiences

Six glowing reviews showcase just how incredible this private tour of Siena and San Gimignano truly is.
Travelers rave about the knowledgeable guides, who make history come alive with their stories. Families appreciate the tailored experiences, ensuring everyone stays engaged.
Guests can’t stop talking about the mouthwatering homemade pasta and the gelato that’s hailed as the best in town.
The vineyard visits offer a delightful escape, with wine tastings that leave a lasting impression.
Frequently Asked Questions
What Should I Wear for the Tour?
For the tour, she’d wear comfortable shoes for walking and breathable layers, since the weather can change. A hat and sunglasses are smart for sunny days, while a light jacket suits cooler mornings.
Are Children Allowed on the Tour?
Yes, children are welcome on the tour! It’s a fantastic experience for families, offering engaging sights and delicious food. They’ll enjoy exploring Siena, San Gimignano, and the scenic Tuscan countryside alongside their parents.
Can Dietary Restrictions Be Accommodated During Lunch?
The tour’s organizers always aim to please, so they’ll likely accommodate dietary restrictions during lunch. Just let them know in advance, and they’ll ensure everyone enjoys the delicious Tuscan cuisine without any worries!
Is There a Restroom Available During the Tour?
During the tour, there’re restroom stops at key locations like Siena and Monteriggioni. It ensures everyone stays comfortable while enjoying the beautiful sights and experiences, making the day more enjoyable for all participants.
What Happens in Case of Bad Weather?
In case of bad weather, the tour organizers adapt the itinerary, often prioritizing indoor activities like wine tastings and guided tours, ensuring everyone still enjoys the experience without missing out on anything special.
The Sum Up
In the end, a private tour from Florence to Siena and San Gimignano is more than just a day trip; it’s a chance to dive into Tuscany’s rich culture and flavors. With charming medieval streets, mouthwatering cuisine, and delightful wine tastings, travelers leave with unforgettable memories and a deeper appreciation for this stunning region. So, if you’re itching for an adventure that combines history, beauty, and good food, this tour is definitely worth considering!
More Guided Tours in Florence
- Florence: Cathedral Duomo Tour with Local Guide
- Florence Old City Street Food Tour and Guided Sightseeing
- Santa Maria del Fiore Cathedral tickets and Audio guide
- Florence: Uffizi Gallery Tickets with Optional audio guide
- Florence: Highlights Walking Tour with Expert Guide
- 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
