Private Tuscany Tour to Siena and San Gimignano with Winery Lunch

Taking a guided day trip through Tuscany’s famous towns is a fantastic way to experience the region’s charm without the hassle of planning every detail yourself. This private tour to Siena and San Gimignano, with a delicious winery lunch, promises a balanced blend of guided exploration and free time to soak in the atmosphere.

What we particularly love about this experience is the personal touch — it’s private, so you get a tailored experience with a knowledgeable guide. Plus, the winery visit offers a genuine taste of local Tuscan life, rounded out by awe-inspiring views of rolling hills and vineyards.

That said, keep in mind the 10-hour schedule is packed, so it’s best suited for travelers with moderate stamina and a love for history, scenic views, and delicious food. If your idea of a perfect day includes charming villages, learning about Tuscany’s past, and savoring local wines, this tour hits the spot.

Key Points

• Private, personalized experience with a dedicated guide and vehicle
• Visit two UNESCO towns, Siena and San Gimignano, with plenty of free time
• Includes a traditional Tuscan farm lunch with organic wine tasting
• Enjoy stunning countryside views and panoramic spots like La Rocca and Rocca of Montestaffoli
• Ideal for history lovers, foodies, and wine enthusiasts seeking authentic experiences
• Well-rated by previous travelers for its knowledgeable guides, seamless organization, and value

The Overview: An Authentic Taste of Tuscany

This tour offers a well-paced journey through some of Tuscany’s most iconic spots, with expert guides leading the way. The journey begins from Florence, where a comfortable, air-conditioned minivan whisks you away into the countryside, giving you your first glimpse of Tuscany’s rolling vineyards and lush hills. The guide’s commentary makes the scenery even more engaging — expect interesting tidbits about the towns and regional history.

One of the standout aspects is the combination of guided and independent exploration. You’ll spend about an hour in Siena, led through its narrow streets, with highlights like Piazza del Campo and the Duomo, before having the freedom to wander and soak in the vibe. Then, after a scenic drive, the visit to San Gimignano is a perfect blend of guided insight and personal discovery.

The Itinerary Breakdown: What to Expect

Florence to Siena (Approx. 1h 15m drive)

The day kicks off with a pickup from Florence. Your guide, whose in-depth knowledge and friendly approach are often praised (many reviewers mention guides like Stefano and Emma), introduces the plan for the day during the comfortable ride. This initial segment is an excellent chance to ask questions and get excited about what’s ahead.

Siena: An Enchanting Medieval City

Once in Siena, the guided walking tour lasts around an hour, during which you’ll explore the city’s most beautiful streets and landmarks. Your guide will point out the oldest surviving bank, Monte dei Paschi di Siena, dating back to 1472, illustrating Siena’s historical wealth and prominence in banking — a fascinating detail that many travelers find surprising.

You’ll also visit a church and museum of one of the 17 contrade (districts), which fosters a deep sense of local identity and pride. The contrasting architecture, the famous Piazza del Campo, and the Duomo di Siena with its stunning marble floor, make this part of the trip memorable. The guide’s storytelling makes the history come alive — one reviewer notes how well the guide explained Siena’s role as a banking hub and its traditions, such as the Palio horse race held twice a year in Piazza del Campo.

Siena Free Time

After the guided tour, there’s sizable free time to explore, shop, or relax in a café. Reviewers have raved about how this mix of guided and solo time allows for a relaxed experience while still seeing the highlights. Many mention the opportunity to visit the Duomo independently, which is well worth the extra time for its intricate floor and frescoes.

Organic Winery and Tuscan Lunch

Next, a short drive takes you to Fattoria Poggio Alloro, an organic family-run estate. Here, you’ll enjoy a traditional Tuscan lunch with homemade pasta, cured meats like prosciutto, local cheeses, and fresh garden salads. The setting is stunning — overlooking fields and vineyards, making the food taste even better.

The winery tour features a tasting of four varieties of wine, exclusive to those 18+. Travelers often praise the farm-to-table feel and the chance to meet local producers. One reviewer calls the lunch “delicious” and notes the gorgeous views that make the experience extra special. The opportunity to purchase local products adds a nice touch for those wanting souvenirs.

San Gimignano: The Towered Town

Post-lunch, the journey continues to San Gimignano, a UNESCO World Heritage Site famous for its medieval towers. This hilltop town is often called the “Manhattan of Tuscany” for its skyline of medieval skyscrapers — only 14 of the original 72 remain, but they’re enough to make a striking impression.

Guided by a detailed map, you’ll have about two hours to explore at your own pace. The town’s narrow streets, shops, and beautiful squares like Piazza Della Cisterna are perfect for wandering, shopping, or enjoying gelato (reviewers confirm Dondoli Gelato is a must-try).

Pockets of Beauty: La Rocca and Rocca of Montestaffoli

For panoramic views, head to La Rocca behind the Duomo or the Rocca of Montestaffoli, a historic fortress turned peaceful garden. Tourists love climbing the towers here for incredible vistas of the skyline and surrounding vineyards.

Return to Florence

Your day wraps up with a restful hour-long drive back to Florence, where many travelers reflect on the well-organized itinerary and the warm, friendly guides who made the experience memorable.

The Value and Experience: What We Think

This tour offers a significant amount of value, especially considering its private nature and carefully curated stops. For around $580 per person, you’re getting a full day of guided visits, cultural insights, and authentic Tuscan food. The inclusion of a winery tour and organic lunch makes this a well-rounded experience, perfect for those who want to indulge in regional flavors without the stress of planning.

Travelers frequently mention the quality of guides as a highlight — with many praising Stefano, Emma, Sara, and Francesca for their knowledge, friendliness, and ability to keep things engaging. The small group format (private or semi-private) allows for a more intimate experience, avoiding the crowded feeling that large bus tours often bring.

The scenic drives and stops at viewpoints like La Rocca and Rocca of Montestaffoli are well-thought-out, offering stunning photo opportunities. Many reviewers note that even in less-than-ideal weather, the day remained enjoyable due to the beautiful scenery and engaging guides.

However, the schedule is quite full, which might be tiring for some. If you prefer more leisure and less rushing, this might not be your best choice. But if you want a rundown of Tuscany’s highlights with a touch of luxury and comfort, this tour truly delivers.

Who Will Love This Tour?

If you’re someone who appreciates history, authentic food, and scenic views, you’ll find this experience rewarding. It’s especially ideal if you prefer private or small group settings where guides can tailor the experience and answer your questions. Food and wine lovers will enjoy the farm lunch and tasting, while those eager to see iconic towns but don’t want to drive or organize each stop will appreciate the seamless itinerary.

This tour is perfect for travelers with a moderate physical fitness level, as it involves some walking and stair-climbing, especially in towns like Siena and San Gimignano. The included transportation and timing make it accessible for most visitors wanting an immersive day without the hassle of self-driving or navigating public transport.

FAQ

Is this tour suitable for vegetarians or those with gluten allergies?
Yes, the lunch includes vegetarian and gluten-free options, so dietary restrictions can usually be accommodated.

How long is the drive between Florence and Siena?
The drive to Siena takes about 1 hour and 15 minutes, giving you a comfortable ride with informative commentary.

Are the wine tastings suitable for minors?
No, wine tasting is only for travelers aged 18 and above, but the rest of the experience remains enjoyable for all ages.

Is there free time to explore each town?
Yes, you’ll have ample free time in Siena and San Gimignano to wander, shop, or relax, as well as guided tours to highlight the must-see spots.

What is the group size?
This is a private tour, meaning you’ll travel with just your group, guided by a dedicated professional, ensuring a personalized experience.

Can I cancel if my plans change?
Yes, the tour offers free cancellation up to 24 hours in advance, allowing flexibility if your schedule shifts.

Final Thoughts

This private Tuscany tour offers a luxurious way to experience Siena and San Gimignano without the stress of planning every detail yourself. With insightful guides, stunning scenery, and delicious food and wine, it delivers a comprehensive taste of Tuscany’s most beloved towns. The mix of guided tours and free exploration time strikes a good balance, giving you the chance to see the highlights and soak in the atmosphere at your own pace.

It’s especially suited for those who value authentic regional experiences — from learning about Siena’s banking past to savoring farm-fresh organic cuisine, and marveling at San Gimignano’s skyline of medieval towers. If you’re after a well-organized day with a personal touch, this tour is a smart choice for your Tuscan adventure.

In summary, this tour is a fantastic way to see Tuscany’s highlights in a day, with the added bonus of expert guides, scenic viewpoints, and a delicious farm-to-table lunch. Perfect for history buffs, food lovers, and those looking to escape the crowds, it offers a memorable slice of Italian life.