Florence: Truffle Hunt, San Gimignano, and Chianti Day Trip

If you’re looking for a way to explore Tuscany beyond the usual sights, this full-day tour packs in some of the region’s best experiences in just seven hours. The focus on a truffle hunt, combined with a visit to the iconic medieval town of San Gimignano and a tasting of local wines and food, makes for a nicely rounded day that stays true to the local vibe. From what we’ve seen, travelers often come away feeling they’ve gained authentic insights into Tuscan life, plus a bunch of fantastic photos.

What really makes this trip stand out are two things: the chance to hunt for truffles with a professional guide and his dogs and the opportunity to try some of the best Chianti wines paired with truffle-based dishes. Plus, the visit to San Gimignano’s towers offers that classic medieval scenery that you simply can’t get enough of.

One thing to consider is the moderate amount of walking involved, as you’ll be hiking through vineyards and woods. While the experience is quite relaxed overall, those with mobility issues might find it a bit challenging. That said, this tour is best suited for travelers who want a hands-on, authentic taste of Tuscany’s culinary and historic highlights without the hassle of planning every detail.

If you’re traveling from Florence and enjoy a mix of outdoor activity, cultural exploration, and good food, this tour could tick a lot of your boxes. It’s especially appealing if you love food, wine, and discovering local traditions in a beautiful setting.

Key Points

• Authentic truffle hunting with dogs and a professional guide
• Tasty Tuscan lunch featuring truffle specialties and Chianti wines
• Exploring San Gimignano’s medieval towers with a local guide
• Stunning countryside views and charming town atmosphere
• Comfortable transportation in a private minivan
• Flexible booking options with free cancellation up to 24 hours in advance

You can check availability for your dates here:

An Honest Look at What to Expect

This tour really captures the essence of a Tuscany day — a little adventure, a lot of good food, and some history wrapped in one. It begins in Florence, where you’ll hop into a cozy, air-conditioned 8-seater minivan with your private group, ready for a scenic drive into the Chianti hills. The journey takes about an hour, giving you your first glimpse of Tuscany’s rolling vineyards and quaint countryside.

The Truffle Hunt Experience

One of the standout moments is meeting the professional truffle hunter. You’ll head out with trained dogs that are expert at sniffing out white truffles — a delicacy prized for their aroma and rarity. Tour reviews praise the knowledge and enthusiasm of the guides, as they reveal secrets about truffles while working with the dogs. One reviewer mentioned, “Selly’s nose is amazing,” highlighting how impressive the dogs can be.

The hike through vineyards and woods isn’t strenuous but involves some moderate walking, so comfortable shoes are a must. Expect to be outdoors, so dressing weather-appropriate, especially waterproof footwear if rain’s in the forecast, is a good idea. As you search for truffles, your guide will share insights into this prized ingredient’s importance in Tuscan cuisine and why it’s so hard to find.

The Lunch and Wine Pairing

Once the truffles are found (or not, but chances are high), it’s time for a delicious Tuscan lunch, where truffle-based dishes take center stage. The reviews mention generous servings of truffles in various preparations, so this isn’t a small taste — it’s a real culinary experience. Paired with some of the best Chianti wines, the meal is meant to restore your energy and deepen your appreciation for regional flavors.

This part of the tour often receives high praise for the quality and authenticity. We’ve seen comments from travelers who loved the variety of truffle specialties and appreciated how the wines complemented the food perfectly. The meal is a highlight for those who enjoy good, local food and want to learn about pairing traditions.

San Gimignano: The Medieval Marvel

After lunch, the day continues with a visit to San Gimignano, often called the “Medieval Manhattan” due to its skyline of medieval towers still standing tall and proud. Your guide will take you through the main sites, sharing stories about the history and architecture that make this town a must-see.

The views from San Gimignano’s vantage points are often described as breathtaking, offering a postcard-worthy backdrop of the surrounding countryside. You’ll also have time to wander, browse artisan shops, or indulge in a gelato made by the world-championship-winning Dondoli — a treat that many reviews mention as a perfect way to cool off and satisfy a sweet tooth.

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Practical Details & Experience

The tour wraps up with a scenic drive back to Florence. The whole experience lasts about 7 hours, which makes it a manageable day trip without feeling rushed. You’ll travel in a private group (though the truffle hunting activity may be shared with a few others), which adds a personalized touch.

The tour is designed to be flexible, with options to cancel up to 24 hours in advance, and you pay nothing upfront — perfect if your plans are still a bit fluid.

Who It’s Best For

This experience suits food lovers, history buffs, and anyone looking for a taste of authentic Tuscany. It’s especially ideal if you’re keen on culinary experiences and outdoor activities. Travelers who enjoy a mix of scenic walks, cultural sights, and delicious local cuisine will find this tour hits the sweet spot.

However, if you have mobility issues or animal allergies, it’s best to consider other options, as there’s some walking involved and the activity involves working with dogs.

Final Thoughts

This tour offers a generous slice of Tuscany, blending culinary discovery, cultural exploration, and outdoor adventure in a way that feels genuine and well-organized. The fact that the guides are knowledgeable and personable really elevates the experience, and the chance to hunt for truffles adds a special, hands-on element that’s hard to find elsewhere.

The quality of the food and wine, combined with the stunning views and charming towns, makes this a standout choice for those wanting a memorable day outside Florence. It’s a well-balanced trip that caters to those interested in local traditions without overdoing it — perfect for anyone who wants to enjoy Tuscany’s essence without the fuss.

If you’re after an authentic, fun, and tasty day out, this tour ticks most boxes. It offers real value for the price, especially considering the personalized touches and the chance to learn from passionate guides.

FAQ

Is this tour suitable for families?
While the tour involves some walking and outdoor activity, it’s generally suitable for those able to handle moderate walking. Children who enjoy outdoor adventures and food experiences may enjoy it, but keep in mind the activity involves dogs and hiking in the woods.

What should I bring?
Comfortable shoes are essential, preferably waterproof if rain is forecast. Bring a camera to capture the scenic views and a weather-appropriate jacket or clothing as needed.

How long is the drive from Florence?
The drive to the Chianti region takes about an hour in comfortable, air-conditioned transport.

What is included in the lunch?
The lunch features several truffle specialties paired with Chianti wines. It’s a generous meal designed to showcase local flavors.

Can I cancel this tour?
Yes, you can cancel up to 24 hours in advance for a full refund, making it flexible if your plans change.

Is the tour private?
Yes, it’s a private group experience, though the truffle hunt may be shared with a few other participants.

Are there options for dietary restrictions?
While not explicitly stated, the meal includes multiple truffle dishes, so special requests should be communicated in advance.

Is there a guide during the whole tour?
Yes, live guides speak English, Italian, and Spanish, providing commentary and assistance throughout the day.

What is the best time of year for this tour?
While not specified, truffle hunting is typically best during the truffle season, which usually peaks in late autumn to early winter. However, reviews suggest the experience is enjoyable year-round.

This Florence: Truffle Hunt, San Gimignano, and Chianti Day Trip seems like a fantastic way to connect with Tuscany’s flavors, history, and scenery in one memorable day.

You can check availability for your dates here: