Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting

Planning a day trip from Florence that combines history, stunning scenery, and a taste of Tuscany’s renowned wine and cuisine? This guided tour offers exactly that, whisking you through two of the region’s most captivating towns—Siena and San Gimignano—with a convenient round-trip transport, a delicious three-course lunch paired with wines, and insights from expert guides.

What we really love about this experience is how it balances guided exploration with free time, giving you space to soak up the atmosphere at your own pace. Plus, the inclusion of a visit to an organic Chianti winery makes it a full, flavorful day. On the flip side, some visitors note that the walking can be quite uphill and the overall pace a little brisk for those who prefer a slower, more relaxed experience.

This tour is ideal for travelers who want to see Tuscany’s highlights without the hassle of driving, and who enjoy combining sightseeing with food and wine indulgence. Whether you’re a history buff, a foodie, or simply eager to enjoy Italy’s beautiful landscape, this trip packs a punch.

Key Points

• Convenient round-trip transport from Florence makes this a stress-free day out.
• Guided tours in Siena and San Gimignano provide context and local insights.
• Wine tasting and a three-course lunch at a Chianti organic winery add a delicious regional touch.
• Flexible free time allows exploration at your own pace in both towns.
• Comfortable transportation with Wi-Fi, USB chargers, and water enhances the journey.
• A mix of guided and independent experiences caters to different travel styles.

Exploring the Towns of Siena and San Gimignano

Starting the Day: From Florence to Siena

The tour begins early at Piazzale Montelungo — a well-located spot for easy access via public transportation. At 8:00 am, the coach departs, and you’ll be greeted by your English-speaking tour leader who will share tidbits about the region as you wind through Tuscany’s scenic hills.

Siena, a UNESCO World Heritage Site, is famous for its medieval streets and the Palio, a historic horse race that still captures the local imagination. The guided walking tour (about an hour) is a highlight, revealing the enchanting secrets of this city’s past and architecture. Reviewers mention guides like Renata, who expertly shares stories with enthusiasm, making history come alive.

One guest noted, “Renata was great! She kept us all on the go and shared many fun and interesting facts along the way.” The guided part is invaluable for understanding Siena’s significance beyond its beauty.

Free Time in Siena

After the guided tour, you’re given about an hour of free time. This is your chance to roam the narrow streets, browse shops, or just soak in the medieval vibe. Reviewers suggest stopping at the main square, Piazza del Campo, or visiting local cafes. Some mention that walking uphill and uneven pavement can be tiring, so comfortable shoes are essential.

A couple of reviews pointed out that the guide in Siena was particularly engaging and showed genuine enthusiasm for the town, which made the free time even more enjoyable. It’s a chance to stumble upon quieter corners or maybe find a cozy gelato spot—highly recommended by those who love to explore on their own.

Visit to Monteriggioni and Wine Tasting

Leaving Siena, the group heads to a renowned Chianti organic winery for a culinary experience. Here, you’re welcomed with sparkling wine before sitting down for a three-course lunch paired with four different wines. Many reviews highlight the quality of the food and wine, calling it a “fabulous farm-to-table experience” with an impressive wine selection.

One reviewer mentioned: “The visit to the winery was good, with 4 different wines served with the lunch. The wines were delicious, and the setting was stunning.” The winery visit adds a relaxing, sensory element to the trip—perfect if you appreciate good wine and authentic regional flavors.

Scenic Drive to San Gimignano

Following the winery, the coach takes you through Tuscany’s iconic landscape—rolling hills, vineyards, cypress trees, and olive groves. This part of the trip is especially praised for the views along the way. Many guests mention that the countryside scenery alone makes the day worthwhile.

Free Time in San Gimignano

Finally, you arrive at San Gimignano, famous for its medieval tower houses and walls. With about 90 minutes of free time, you’re encouraged to wander the narrow streets, admire the skyline dotted with towers, and take in the medieval charm. Many reviews rave about the opportunity to explore on their own, with some guides offering tips on where to get the best gelato or how to climb up for panoramic views.

One guest said, “We wished we had more time here, but the town is perfect for wandering, sightseeing, and taking photos.” The steep uphill walks can be challenging but are well worth it for the views and atmosphere.

Practical Details & What to Expect

Transportation and Comfort

The tour provides round-trip transport on a private, air-conditioned coach equipped with Wi-Fi, USB chargers, and water—small details that make a big difference on a full day of travel. The group size is capped at around 50, which strikes a good balance between socializing and personal space.

Guided Tours and Free Time

The guided tours in Siena (from April to October) and San Gimignano give you historical context and local flavor, making the experience richer than just sightseeing. The free time is your chance to explore independently, shop, or relax.

Food and Wine

For many, the highlight is the lunch and wine tasting at the Chianti winery. The meal includes a 3-course menu, with wine pairings that many reviewers find impressive—delicious, well-paired, and giving a true taste of regional produce.

Duration and Pace

The entire day lasts about 9 hours, with a start time of 8:00 am. The itinerary is quite packed, and some reviews point out significant walking—uphill, uneven pavements, and walking to and from the bus. It’s a good idea to wear comfortable shoes and be prepared for some physical activity.

Price and Overall Value

At $114.95 per person, this tour offers a lot: guided exploration, free time, lunch, wine tasting, and transport—all in one package. Reviews suggest that the experience is considered good value, especially given the quality of the guides, scenery, and included meals.

Authentic Insights from Travelers

Many reviews praise the guides, highlighting their knowledge, humor, and ability to keep everyone engaged. For example, one guest said, “Renata was very helpful and informative,” adding that her tips made the day even better.

The scenery consistently impresses visitors, with comments like “the views along the way were stunning” and “seeing Siena and San Gimignano perched high on their hills was incredible.” The wine tasting and lunch are also frequently mentioned as a highlight, with several reviewers calling it “beyond their expectations” for regional authenticity and quality.

A few reviewers noted the walking can be quite strenuous, especially uphill and on cobblestones, so packing comfortable shoes and being prepared for some physical activity is wise.

The Sum Up: Who Is This Tour Perfect For?

This day trip from Florence is best suited for travelers who want to see Tuscany’s iconic towns without the stress of driving. It’s perfect for those who appreciate a mix of guided history, free exploration, and regional food and wine. It strikes a balance between structured tours and independent wandering, making it suitable for a variety of travelers—whether you’re a history buff, a foodie, or just want to enjoy Italy’s stunning scenery.

The inclusion of a quality lunch and wine tasting elevates the experience, adding value for those looking to indulge in local flavors. The scenic drive, paired with engaging guides, ensures that you’ll leave feeling like you’ve experienced some of Tuscany’s best without feeling rushed.

However, be prepared for some walking uphill and uneven pavements—comfortable footwear is a must. If you’re OK with a busy pace and want a convenient, well-rounded day out, this tour is a terrific way to discover these medieval gems.

FAQ

What time does the tour start?
The tour departs at 8:00 am from Piazzale Montelungo in Florence.

How long is the entire day?
It lasts approximately 9 hours, including travel, guided tours, free time, and meals.

Is transportation comfortable?
Yes, the coach is air-conditioned, equipped with Wi-Fi, USB chargers, and water, making the journey enjoyable.

Are guided tours available in Siena?
Yes, from April to October, there’s a guided tour of Siena with an English-speaking local guide; from November to March, exploration is self-guided.

What is included in the lunch?
A three-course meal with wine pairing, including a tasting of four different wines, is included at an organic winery.

Can I customize dietary restrictions?
Yes, vegetarians and those with dietary restrictions should inform at booking; alternatives are available.

How much free time do I get?
In Siena, about an hour; in San Gimignano, roughly 90 minutes.

Are there any physical challenges?
Yes, both towns involve uphill walking and uneven pavement, so comfortable shoes are recommended.

Is there Wi-Fi on the coach?
Yes, the coach provides Wi-Fi, facilitating connectivity throughout the day.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the tour, with a full refund.

The Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting offers a fantastic way to see Tuscany’s highlights in one well-organized, immersive day that balances guided insight with personal exploration—perfect for those wanting a taste of Italy’s medieval charm and culinary delights without the hassle of planning all the details themselves.