From Florence: Siena & San Gimignano Guided Tour and Dinner

Traveling through Tuscany without experiencing its medieval towns and rolling hills almost feels like missing the soul of Italy. This guided tour from Florence promises a full day of discovering Siena and San Gimignano, two towns that showcase the region’s timeless charm, topped off with a sunset dinner amidst the Chianti hills. While we haven’t done the experience ourselves, the reviews and details paint a picture of a well-organized, memorable day.

What we love about this trip: the intimate small-group setting, the opportunity to see UNESCO World Heritage Sites, and the chance to enjoy a typical Tuscan dinner with regional wines. The scenic drives through the hills, combined with expert guides, make it a well-rounded experience. The only thing to keep in mind is the limited free time, especially in San Gimignano, which might leave some wanting to explore the narrow back streets a bit longer.

This tour is ideal for those who want a good overview of Tuscany’s highlights without the hassle of planning logistics. Perfect for first-timers, history buffs, and wine lovers, it offers a blend of culture, cuisine, and scenic beauty in a manageable day.

Key Points

• Intimate Small-Group Setting: Enjoy a more personal experience with fewer people.
• Expert Guides: Knowledgeable drivers and tour leaders make history come alive.
• UNESCO Sites: Visit Siena’s historic center and San Gimignano’s medieval skyline.
• Stunning Sunset Dinner: Dine at a countryside winery with panoramic views.
• Flexible Options: Choose between a standard coach or a premium Mercedes minibus.
• Upgrade Possibility: Add Pisa for a full day of Tuscan exploration.

You can check availability for your dates here:

What to Expect from This Tour

This journey from Florence is a well-crafted mix of sightseeing, tasting, and scenic views. Its structure balances guided walks with free time, allowing you to absorb Tuscan life at a comfortable pace.

Transport and Group Size

Depending on your booking, you’ll travel in either a coach or a Mercedes minibus. The smaller Mercedes option is praised by reviewers like Emily, who mentioned her driver Romana’s delightful storytelling and attentiveness. The vehicle is air-conditioned, ensuring comfort through the long day. The small group size means you’re less likely to feel lost in a crowd and can ask questions easily—Nancy appreciated the personable guides.

Siena: A Medieval Marvel

Our first stop is Siena, a city that rivals Florence in artistic and architectural splendor. The guided walking tour takes you through Piazza del Campo, where the legendary Palio horse race takes place twice a year. Nancy highlighted how Siena feels cooler and less crowded in the afternoon, giving the best vibe for exploring its cobbled streets and alleys.

The guide provides insights into Siena’s contrade—its fierce neighborhood identities—which bring the city’s history alive. Reviewers like Mary S. appreciated the passionate guides who shared humorous and interesting anecdotes, making the history memorable. Keep in mind that your time in Siena is limited, so you’ll want to make the most of the tour.

San Gimignano: The Manhattan of the Middle Ages

Next, the tour takes you through rolling Tuscan hills to San Gimignano, famous for its skyline of medieval towers. Here, you’ll have about an hour for self-guided exploration, giving you some freedom to wander. Expect to see artisan shops, enjoy a gelato, and take in views from the city walls.

Reviewers like Nancy wished for a little more time to explore some of the back streets, but generally, the self-guided time is enough to soak up the atmosphere. The towers create a fairy-tale setting, and the panoramic vistas toward the countryside leave a lasting impression.

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Sunset Dinner in Chianti

The highlight for many is the evening: a traditional Tuscan dinner set against a backdrop of golden sunsets over the Chianti hills. This isn’t just a meal; it’s an experience. Sitting at a countryside farmhouse or wine estate, you’ll feast on locally sourced dishes like lasagna, paired with regional wines. Nancy called it “the highlight of the trip,” especially praising the farm’s delicious food and friendly hosts.

Reviewers like Nicole described this as a “once-in-a-lifetime” experience, emphasizing how special it felt to dine in such a scenic, intimate setting. The dinner is included in the price, adding excellent value for a memorable, authentic meal that complements the day’s sightseeing.

Returning to Florence

After a leisurely dinner, you’ll head back in the quiet comfort of your vehicle, with plenty of opportunity to reflect on the day’s sights and tastes. The tour typically ends back at the original meeting point, ready to share stories and photos.

The Value of This Experience

The full-day itinerary covers two of Tuscany’s most iconic towns, plus a spectacular sunset in the Chianti hills. The inclusion of guided tours, a wine tasting, and a dinner makes this a good value, especially considering the small-group atmosphere and expert guides. The upgraded Tuscany Grand Tour extends the day to include Pisa, providing a deeper dive into the region’s art, architecture, and history.

Pricing is competitive for a guided, all-inclusive experience. The small-group format ensures personalized attention, and the scenic drives through lush hills are a highlight in their own right. The guide’s enthusiasm and knowledge, often noted in reviews, add depth to the experience, transforming sightseeing into storytelling.

Transport: Comfort & Convenience

Traveling in a Mercedes minibus or coach greatly enhances the comfort, especially for a long day. The small-group size means you’re less likely to experience the chaos of large tours, which many reviewers appreciate. Romana’s storytelling, her sharing of local stories, and her attention to detail make the drive an enriching part of the day.

Timing & Duration

With durations of about 8.5 to 12 hours, this tour suits those with a full day available. Starting times check your availability, but generally, you’ll be out from morning until early evening. Keep in mind that the limited free time in San Gimignano might feel rushed if you’re eager to explore every alley or shop.

Who Should Consider This Tour?

This experience is perfect for travelers who want a well-organized, intimate group tour that balances sightseeing with leisure. It’s ideal for first-time visitors to Tuscany who want a broad overview, as well as those interested in local wines and authentic regional food. The guided component enriches your understanding of Tuscany’s history and culture, making it a smart choice for history buffs and foodies alike.

Active travelers who prefer a more relaxed pace and appreciate scenic drives will find this tour highly satisfying. However, those with mobility issues should note that Siena’s cobblestone streets and the walking involved might pose some challenges.

FAQs

Is transportation included in the tour?
Yes, round-trip transportation is provided in a comfortable minivan or coach, depending on your chosen option.

Can I join this tour from my accommodation?
No, the tour starts at Via dei Vagellai 22R in Florence; pickup at your accommodation is not included.

What’s the group size?
The small-group tours typically feature fewer participants, providing a more personal experience. You can choose between a standard coach or a premium Mercedes minibus.

How long is the guided tour of Siena?
The guided walk in Siena lasts around 5.5 hours, including sightseeing, shopping, and exploring the historic center.

How much free time is there in San Gimignano?
You’ll have approximately an hour for self-guided exploration, which is enough to see the main sights and grab a gelato.

What does the dinner include?
The dinner features locally sourced dishes and regional wines, usually served at a countryside farmhouse or wine estate, with the sunset as a backdrop.

Can I upgrade to the full Tuscany Grand Tour?
Yes, the Grand Tour option adds Pisa to the itinerary and includes a Tuscan lunch, making it a full-day adventure.

Is this tour suitable for children or people with mobility issues?
It’s best suited for those without mobility impairments due to walking on cobbled streets. Children are welcome, but keep in mind the long day.

What is the cancellation policy?
You can cancel up to 24 hours in advance for a full refund, offering flexibility if your plans change.

This guided tour from Florence offers a beautifully balanced day of history, scenic drives, and authentic Tuscan flavors. The small-group setting fosters a more personal and immersive experience, making it ideal for travelers who want to see the highlights without the hassle of self-organizing.

You’ll visit Siena’s UNESCO-listed historic center, marvel at San Gimignano’s medieval towers, and enjoy a sunset Tuscan dinner in the hills—creating memories that taste as good as they look. The knowledgeable guides, stunning landscapes, and regional wines make this a worthwhile choice for anyone eager to experience Tuscany beyond just the surface.

If you’re after a relaxed, well-organized day that combines culture, scenery, and cuisine in one package, this tour is definitely worth considering. It’s a chance to see iconic towns, indulge in local flavors, and watch the sunset over rolling hills—all in one seamless day.

Note: Always check current availability, starting times, and specific inclusions when booking, as details may vary.

You can check availability for your dates here: