From Florence: Siena, San Gimignano & Tuscany – Small Group

Exploring Tuscany in a Day: A Detailed Look at the Small Group Tour from Florence

Taking a full day to explore Tuscany’s iconic towns and landscapes sounds ambitious, but this small group tour from Florence makes it achievable and enjoyable. With a well-organized itinerary, expert guides, and a cozy 8-seat minivan, this experience offers a practical way to tick off several highlights without the hassle of planning. It’s ideal for first-time visitors eager to see Siena, San Gimignano, and the Chianti wine region, all in one day.

What we love most is the personalized approach—small groups mean fewer crowds, more flexibility, and a guide who can share insider tips and local stories. The included wine tasting and Tuscan lunch elevate the experience, giving you a genuine taste of the region’s culinary delights. On the flip side, the full schedule means a fair amount of driving and walking, which might be tiring for some. Still, if you’re after a comprehensive, hassle-free day that combines culture, scenery, and flavors, this tour hits the mark.

This tour suits travelers who are short on time but want a meaningful taste of Tuscany. It’s especially good for those who appreciate guided insights and prefer avoiding the logistical headaches of independent day trips. Families, couples, or groups of friends who enjoy a relaxed, curated itinerary will find it particularly appealing.

Key Points

• Efficient sightseeing: Cover multiple towns and regions in a single day, perfect for first-time visitors.
• Small group setting: No large bus crowds, more personalized attention, and a relaxed atmosphere.
• Expert guides: Insights and local stories enhance each stop, making the experience richer.
• Regional flavors: Tasting local wines, olive oils, and a traditional Tuscan lunch highlight regional culinary traditions.
• Comfortable transport: An 8-seat minivan ensures a cozy journey with scenic views.
• Flexibility: Free time in Siena and San Gimignano allows for personal exploration.

The Itinerary in Detail

Starting Point in Florence

Your day begins early, at 8:45 am, near Porta Romana in Florence. The small group departs by minivan, setting the tone for an intimate, engaging day. The tour’s timing is designed to make the most of daylight and includes scenic drives through the Tuscan countryside, which are as captivating as the destinations themselves.

First Stop: Monteriggioni

The first leg takes you to Monteriggioni, a beautifully preserved medieval fortress town. Just 40 minutes from Florence, this small village offers a glimpse into Tuscany’s past with its well-preserved walls and towers. It’s also a filming location for The Gladiator and a favorite for fans of history and movies alike.

Travelers mention that Monteriggioni’s charm lies in its authenticity, with many noting it’s a peaceful spot for quick photos and wandering. While free to explore, don’t miss the opportunity to walk along the ramparts—some reviewers say it’s a mini step back in time.

Siena: The Heart of Tuscany

Next, the tour heads to Siena, where the group spends around two hours. Your guide provides an orientation walk, pointing out highlights like artisan shops and the Piazza del Campo, famous for the Palio horse race. The Piazza’s shell shape and vibrant atmosphere make it a perfect place for photos and people-watching.

A visit to Siena’s Cathedral is highly recommended—its intricate façade and stunning interior are worth the extra time. Reviewers highlight the value of the guide’s insights, which often include hidden corners and local stories that enrich your understanding of Siena’s culture.

There’s also time for some leisure here, whether you want to relax at a café or explore on your own. The balance of guided and free time helps visitors soak in the atmosphere without feeling rushed.

Oenological Experience in Ulignano

The journey then takes you into Chianti, the renowned wine region. You’ll stop at a local winery for about an hour, where you get to taste seven wines, along with olive oils and balsamic vinegar. The Tuscan lunch served here—featuring bruschetta, pecorino, cured meats, lasagna with truffle oil, and traditional Ribollita soup—is a hearty and authentic meal.

This stop is often praised for its quality wine selection and the opportunity to learn about production from passionate local producers. One reviewer mentions that Antonello, the guide, even arranged for a taste of a wine not initially on the tasting menu, adding a personal touch.

San Gimignano: The Manhattan of Tuscany

From the winery, the tour proceeds to San Gimignano, a UNESCO World Heritage Site famous for its medieval towers. The guide provides maps and tips for exploring, but the hour-long free time allows for wandering at your own pace.

Tourists love San Gimignano’s cobblestone streets, panoramic views, and quaint piazzas. It’s a chance to soak up the town’s timeless charm, and many comment that the town’s skyline with its towers is breathtaking. The town’s small size makes it perfect for a relaxed exploration, whether you want to shop, snap photos, or sample local gelato.

Return to Florence

The journey concludes with a scenic drive back to Porta Romana in Florence around 6 pm. The relaxed pace and comfortable transport mean you arrive ready to unwind or continue exploring the city’s evening scenes.

What Makes This Tour Stand Out

Guided insights from passionate locals like Lorenzo and Christina elevate the experience. Multiple reviews highlight the guides’ knowledge and flexibility, making sure you get the most out of each stop without feeling hurried. Christina’s ability to share local lore, along with Antonello’s tips and extra wine tastings, add a personal touch many travelers remember fondly.

The small group size (max 8 travelers) ensures a more intimate day, where personal questions and spontaneous stops are welcomed. Reviewers also mention the value of avoiding large bus tours, which can feel impersonal and rushed.

The inclusion of transportation, a guided walk, wine tasting, and lunch makes this a considerable value, especially given the region’s high-quality food and wine. The price of around $290 per person might seem steep at first glance, but considering the inclusions and the hassle-free logistics, many find it a fair trade.

However, the full schedule means you’ll be on the move for most of the day, and some might find the early start and tight timing a bit exhausting, especially if they prefer a more leisurely pace. Also, because the tour requires at least three participants, it’s worth booking in advance to secure your spot.

Final Thoughts

This From Florence to Siena, San Gimignano & Tuscany small group tour offers a fantastic way to see the region beyond Florence’s borders, combining history, culture, and wine in a single day. Its highlights include expert guides, authentic Tuscan food and wine, and the comfort of a small, intimate setting.

If you’re a traveler eager to maximize your time without sacrificing depth, this tour is a smart choice. It’s especially suited for those who prefer curated experiences and enjoy learning about local traditions directly from passionate guides. The balanced mix of guided exploration and free time in charming towns makes for a memorable day, perfect for first-timers or those wanting a taste of Tuscany’s best.

For anyone seeking an easy, well-organized way to experience Tuscany’s highlights without the hassle of planning or driving, this tour delivers both value and authenticity.

FAQ

Is transportation included in this tour?
Yes, the tour includes transport on a cozy 8-seat minivan, making it easy to relax and enjoy the scenery while traveling between stops.

How long is the total tour?
The entire experience lasts approximately 9 hours, starting around 8:45 am and ending back in Florence at about 6 pm.

What’s the group size?
This tour is limited to a maximum of 8 travelers, ensuring a personalized experience with plenty of opportunities for questions and spontaneous stops.

Are meals included?
Yes, a Tuscan lunch featuring antipasti, lasagna with truffle oil, and traditional Tuscan soups is included, along with wine and olive oil tastings.

Can I customize or extend my time in towns like Siena or San Gimignano?
The tour provides free time in these towns, allowing you to explore at your own pace before returning to the van for the scenic drive back.

What if I have dietary restrictions?
Vegetarian, vegan, and gluten-free options are available upon request, ensuring everyone can enjoy the meal.

Do I need to book in advance?
Yes, as this tour is popular and requires a minimum of 3 participants. Booking ahead ensures your spot.

Are there any hidden costs?
All major inclusions are covered, but extras like souvenirs or additional drinks are at your own expense.

What is the cancellation policy?
You can cancel for free up to 24 hours before the tour, receiving a full refund. Cancellations within 24 hours are non-refundable.

In summary, this small group tour from Florence to Tuscany offers a thoughtfully curated, authentic experience that balances sightseeing, tasting, and culture. It’s ideal for travelers wanting a comprehensive taste of Tuscany’s most famous spots, all while enjoying the comfort and intimacy of a guided small group adventure.