Exploring the historic towns of Tuscany is a dream for many travelers. This private tour from Florence promises an immersive experience, taking visitors to the medieval marvels of Siena and San Gimignano. With a local guide leading the way, you’ll discover the iconic landmarks, indulge in a traditional winery lunch, and uncover the charming character that makes this region so captivating. Whether you’re seeking a cultural adventure or a taste of the Tuscan lifestyle, this tour offers a well-rounded glimpse into the heart of this enchanting part of Italy.
Key Points

- This private Tuscany tour provides an immersive exploration of the medieval towns of Siena and San Gimignano, with a traditional winery lunch included.
- The tour starts at 8:30 AM in Florence and includes round-trip transportation, a professional English-speaking guide, and free cancellation up to 24 hours in advance.
- Highlights of the itinerary include a guided walking tour of Siena, free time for independent discovery, and a visit to a family-run organic winery for a traditional Tuscan lunch and wine tastings.
- The tour is not wheelchair-friendly, but strollers are allowed, and a moderate fitness level is required, with restrictions for infants and participants under 18 at the winery.
- Based on 18 reviews, the tour has an average rating of 4.9 out of 5, with praise for the knowledgeable and friendly guides, beautiful scenery, and excellent food experiences.
Tour Overview
This private Tuscany tour offers travelers a full-day experience exploring the medieval towns of Siena and San Gimignano.
The tour starts at 8:30 AM in Florence and includes transportation, a professional English-speaking guide, and a traditional winery lunch.
In San Gimignano, visitors can wander the historic streets, admire the iconic towers, and sample local gelato.
The tour then continues to a family-run organic winery for a guided tasting and hearty lunch.
The final stop is Siena, where travelers can marvel at the stunning Duomo and Piazza del Campo during a guided walking tour.
The tour is priced at $534.66 per person with free cancellation up to 24 hours in advance.
Here are more experiences we've reviewed in Florence
Itinerary Highlights

The tour begins with a scenic drive from Florence to the medieval town of San Gimignano, where travelers can explore its charming streets and iconic towers at their own pace.
Next, the group visits an organic family-run wine estate for a traditional Tuscan lunch paired with tastings of the estate’s wines.
After lunch, the tour moves on to the historic city of Siena, where a guided walking tour showcases the Duomo and the famous Piazza del Campo.
Guests have free time in Siena to shop, relax in cafés, or further discover the city’s sights.
Inclusions

According to the information provided, the private Tuscany tour includes an air-conditioned vehicle for transportation.
The tour also features a professional English-speaking guide who’ll provide maps and information about the towns visited.
Travelers can enjoy a hearty farmhouse lunch with vegetarian and gluten-free options at a family-run organic winery, along with a tour and wine tasting for those 18 and older.
The package includes a guided walking tour of Siena, with entrance fees to the cathedral.
Hotel pickup and drop-off are also provided, though gratuities aren’t included in the tour price.
Tour Restrictions and Accessibility

While the private Tuscany tour offers an immersive experience, it’s not accessible to all travelers. The tour isn’t wheelchair-friendly, though strollers are allowed. Infants must sit on laps during transport.
Those with back problems or serious medical conditions shouldn’t join, as the tour requires a moderate fitness level. Only those 18 and older can participate in the winery tour and tasting.
Despite these limitations, the tour provides an engaging way to explore Tuscany’s historic towns and enjoy regional cuisine. Guests should consider their abilities and needs before booking to ensure a comfortable and enjoyable experience.
Customer Reviews and Experiences

With an average rating of 4.9 based on 18 reviews, the private Tuscany tour has been overwhelmingly praised by travelers.
Highlights include the knowledgeable and friendly guides, the beautiful scenery, and the excellent food.
Travelers commonly praised the lunch at the winery and the overall organization of the tour. They appreciated the balance of guided experiences and free time.
Guides like Stefano, Sara, and Francesca received notable mentions for their exceptional service and local insights.
The tour provides an excellent value, delivering a memorable Tuscan experience that exceeds expectations.
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
- Florence: Pasta Cooking Class With Unlimited Wine
- Wine Safaris: off Road Tuscany Wine Tours and Lunch From Florence
- Tuscany Bike Tours Through the Chianti Hills With Wine Tasting
A Closer Look at the Winery Lunch

A key highlight of the private Tuscany tour is the hearty farmhouse lunch served at the organic family-run wine estate. Guests can expect:
-
A traditional multi-course meal featuring locally-sourced, seasonal ingredients
-
Vegetarian and gluten-free options to accommodate various dietary needs
-
A guided tour of the winery and an opportunity to taste the estate’s award-winning wines
-
Stunning views of the surrounding vineyards and rolling Tuscan hills
-
A relaxed and authentic dining experience that immerses visitors in the region’s culinary traditions.
The winery lunch is a delicious and memorable part of this comprehensive Tuscan day trip.
Discovering the Medieval Charms of Siena and San Gimignano

After the indulgent winery lunch, the private Tuscany tour takes visitors on a journey to explore the medieval charms of Siena and San Gimignano.
In Siena, the guided walking tour reveals the grandeur of the Duomo and the lively Piazza del Campo. Travelers enjoy free time to shop, sip coffee, and admire the city’s distinctive architecture.
Next, the tour heads to the hilltop town of San Gimignano, known for its iconic skyline of medieval towers. Visitors wander the quaint streets, sample delectable gelato, and take in panoramic vineyard views.
The perfect blend of guided exploration and independent discovery.
Common Questions

How Far Is the Tour From Florence?
The tour departs from Florence, so the distance is not too far. It’s a convenient day trip option, allowing travelers to explore the charming towns of Siena and San Gimignano without having to travel a long distance from the city.
Do Guide Tips Need to Be Paid Separately?
Gratuities are not included in the tour price, so tips for the guide are to be paid separately at the end of the tour. This allows travelers to provide a tip amount they feel is appropriate based on the guide’s service.
Can Dietary Restrictions Be Accommodated?
The tour offers hearty farmhouse lunches with vegetarian and gluten-free options, accommodating various dietary needs. Travelers are advised to inform the provider of any special requirements when booking to ensure their needs are met during the tour.
Is There a Dress Code for the Winery Visit?
There’s no formal dress code for the winery visit. Comfortable, casual attire is recommended. The tour provider can accommodate dietary restrictions – just let them know ahead of time. This helps ensure an enjoyable, budget-friendly experience.
Are There Any Discounts Available for Larger Groups?
Yes, this tour offers discounts for larger groups. The more people in your party, the more you’ll save per person. Contact the tour operator for details on group pricing and availability.
The Sum Up
This private Tuscany tour is the perfect way to learn about the charm and history of Siena and San Gimignano. With a guided experience at a family-run winery, you’ll savor the finest local flavors and wines. Explore the medieval streets, admire the iconic architecture, and create unforgettable memories in these picturesque Tuscan towns. This tour offers an unbeatable combination of guided exploration and free time, making it an excellent value for your travel budget.
More Historical Tours in Florence
- Florence Medici Bike Tour Cycle Through History and Power
- Florence Wine &Food: Taste Tuscan Flavors in Historic Cellar
- Florence: Guided visit of architecture and history
- Guided Medici Tour Florence: Discover Mysteries & History
- The History of Florence: The Renaissance Era Private Tour
- Florence Tour: Michelangelo’s David and Historic Center
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
