Private Tour of San Gimignano & Siena

Discovering Tuscany: A Private Tour of San Gimignano & Siena

Planning a day trip through Tuscany often feels like trying to pick just one favorite dish — impossible! But if you’re after a well-rounded taste of Italy’s medieval charm, this private tour of San Gimignano and Siena from Florence could be just what you need. It’s a thoughtfully designed experience that balances guided sightseeing, local food and wine, and free time to soak in the scenery at your own pace.

What we really appreciate about this tour is how it combines the best of both towns: San Gimignano’s iconic towers and medieval streets and Siena’s stunning Gothic architecture and historic piazzas. Plus, the private aspect means you’re not stuck in a large group, and the inclusion of a licensed guide ensures you get personalized insights that truly bring the place to life.

On the flip side, one thing to keep in mind is that lunch, entrance fees, and tastings are not included in the tour price. This means budgeting extra for meals and activities. Also, since it’s around a 9-hour day, it’s best suited for those comfortable with a full schedule and a fair amount of walking. This tour hits the sweet spot for travelers who want a curated, hassle-free experience with a local touch—perfect for first-timers, small groups, or anyone eager to explore Tuscany with expert guidance.

<h3 id="section-0">Who is this tour for?

If you’re looking to blend sightseeing with culinary delights, enjoy small-group intimacy, and value knowledgeable guides, this will likely be a great fit. It’s especially ideal for those who want to maximize their day without the stress of planning logistics or navigating public transportation.

Key Points

• Private experience means personalized attention and flexibility for your group
• Includes transportation from Florence—no worries about driving or parking
• Guided walking tours in both towns add context and stories to your visit
• Free time in San Gimignano for shopping and sightseeing
• Wine and olive oil tastings available nearby (not included in price)
• Flexible cancellation policy offers peace of mind with full refunds up to 24 hours ahead

Exploring Tuscany: The Itinerary in Detail

Starting the Day with San Gimignano

Your adventure begins early, with pickup service from Florence, setting the tone for a relaxed day. The drive takes about 4 hours, giving you a chance to enjoy the rolling landscapes of Tuscany—think patchwork fields, cypress-lined roads, and quaint farmhouses. Once you arrive at San Gimignano, you’re stepping into a picture-perfect medieval village famous for its 13th-century towers that loom over the skyline. These towers symbolize the wealth and power of the merchants who built them, and they remain a defining feature today.

The guided walk here lasts about an hour, during which your guide will point out highlights like the Duomo and Cisterna square. We loved how guides often sprinkle in stories and historical snippets—making it more than just a walk through old streets. Afterwards, you get free time for shopping—especially tempting for those artisanal shops selling linen, pottery, olive oil, and local wines. Many travelers, like Melissa, have noted that the guide’s knowledge and recommendations really enhance the experience, making it more memorable.

Wine Tasting and Lunch Near San Gimignano

Next, a short drive takes you to a local winery for a tasting session. Here, you can enjoy at least five different wines, along with extra virgin olive oil tastings—perfect for wine lovers or anyone interested in learning how Tuscany’s top-quality products are made. Keep in mind, this tasting and lunch are not included in the tour price, so plan accordingly.

The winery visit offers a behind-the-scenes look at vineyard life, adding a sensory dimension that only a local producer can provide. Many reviews highlight how these tastings elevate the trip, especially when paired with the stunning scenery of the vineyard backdrop. If you’re a foodie, this part of the day is often a highlight—though it’s an extra expense you’ll want to factor into your budget.

Siena: Gothic Grandeur and Cultural Gems

After lunch, the journey continues with about 45 minutes of driving to Siena. This city exudes a different vibe—more Gothic in style, with a rich history tied to the famous Palio horse race. You’ll visit the San Domenico church, home to relics of Santa Catarina da Siena, a beloved saint. Then, a quick stop at the shell-shaped Campo square offers a chance to snap photos, learn about the Palio, and absorb the lively atmosphere.

Your guide will point out the exterior of the Palazzo Pubblico, Siena’s historic town hall, before heading inside the Cathedral of Siena (Duomo). This Gothic masterpiece is renowned for its stunning façade and intricate interior, offering a feast for the eyes and a glimpse into medieval craftsmanship. It’s easy to see why this cathedral is considered one of Italy’s finest Gothic churches.

Reviews from Ludmilla praise Giuseppe, the guide, for his love of the area and his ability to share both the present-day vibe and historical context. The 2-hour Siena visit blends sightseeing with stories, making the city’s artistic and religious significance come alive.

Transportation, Timing & Comfort

The entire journey is done in an air-conditioned vehicle, which makes the long day more pleasant, especially during warmer months. The private transport is a big plus—no waiting around for large groups or shuttles, and the flexible schedule means you won’t feel rushed. The entire tour lasts approximately 9 hours, with pickup at 8:00 am, allowing a full day of exploration.

Group size is capped at 8 people, so it’s intimate without feeling crowded. This makes conversations easier, guides more attentive, and the experience more personalized—a real treat if you prefer avoiding large tourist buses.

Cost and Value Considerations

For around $1,292 per group (up to 8 people), you get private transportation, guided tours, and the flexibility to explore at your own pace. When you consider the personalized service, the convenience of door-to-door pickup, and the insider knowledge from guides like Paola and Giuseppe, the value isn’t just in ticking boxes but in the quality of experience.

Remember, lunch and tastings are extras, so you’ll want to budget for those if you’re interested. Given the reviews praising guides’ knowledge and the carefully curated itinerary, many find this tour worth the price—especially if you value a comfortable, guided, and intimate day out.

Final Thoughts

This private tour of San Gimignano and Siena offers a well-rounded taste of Tuscany’s cultural treasures, scenic beauty, and culinary delights. It’s especially suited for those who appreciate local stories, want expert-guided insights, and dislike big crowds. The small-group setting lets you soak in the atmosphere without feeling rushed, making it a great way to see two of Tuscany’s most iconic towns in one day.

While the extra costs for lunch and tastings require some planning, the overall experience delivers a smoother, more personal connection to the region. The knowledgeable guides, stunning scenery, and charming towns make this tour a memorable choice for travelers eager to get a genuine feel for Tuscany’s magic.

If you’re after a balanced mix of sightseeing, culture, and local flavor—without the hassle of organizing everything yourself—this private tour is definitely worth considering.

FAQ

Is transportation included in this tour?
Yes, private round-trip transportation from Florence is included, so no need to worry about driving or parking.

What’s the duration of the tour?
The full experience is approximately 9 hours, starting around 8:00 am with pickup.

Can I cancel this tour?
Yes, the tour offers free cancellation up to 24 hours before the start, with a full refund.

Are meals included?
No, lunch and tastings near San Gimignano are not included but can be purchased separately.

How many people can join this tour?
The private tour is designed for groups of up to 8 people, ensuring a personalized experience.

What are the main highlights?
You’ll visit San Gimignano’s medieval streets and towers, enjoy a wine and olive oil tasting, and explore Siena’s Gothic cathedral and historic square.

Is this tour suitable for families or children?
While mainly designed for adults, the itinerary’s focus on walking, sightseeing, and tasting makes it generally suitable for older children who can handle the day’s pace.

Do I need to prepare anything?
Bring comfortable shoes, some cash for extra tastings or souvenirs, and a camera to capture the beautiful scenery.

What language is the guide speaking?
Guides are licensed and typically speak English, providing detailed commentary throughout the day.

Is the tour customizable?
It’s a private experience, so there’s room for some flexibility—discuss your preferences with your guide beforehand.

Overall, if you’re after a thoughtfully curated, intimate day exploring Tuscany’s highlights with knowledgeable guides, this tour could be just right. It balances sightseeing, culture, and local flavors, making it a worthwhile option for many travelers.