“Sweet Hills of Chianti & San Gimignano” with Lunch & 2 Tastings

This carefully curated tour offers a scenic escape from Florence that blends picturesque landscapes, historical towns, and authentic Tuscan flavors. Priced at around $259 per person, it’s marketed as a full-day experience—about eight hours—that combines sightseeing, wine tasting, and a delicious farm-to-table lunch. What makes this trip stand out is its intimate, private-group setting, allowing for a more relaxed and personalized adventure through some of Italy’s most treasured spots.

One of the highlights we love is the seamless way this tour balances guided and self-guided moments, giving travelers freedom without the hassle of planning logistics. Plus, the inclusion of two wine tastings at different local wineries means you’ll get a genuine taste of the region’s diverse wines, from Chianti to Vernaccia. However, for those who prefer a more structured or tightly scheduled day, the flexible itinerary might feel a bit laid-back.

This tour is ideal for those who want to combine scenic beauty, historical charm, and culinary delights all in one day. It’s perfect if you’re traveling with friends or family and cherish moments of authentic Tuscany—without sacrificing comfort or convenience.

Key Points

• Private, Comfortable Transport: Travel in an air-conditioned vehicle with a local driver, making the journey relaxing and stress-free.
• Authentic Food & Wine: Enjoy a 3-course Tuscan farm lunch paired with multiple wine tastings, including Chianti, Vernaccia, and Super Tuscan.
• Rich Cultural Stops: Visit San Gimignano’s medieval towers, explore the fortified walls of Monteriggioni, and see traditional Chianti wineries.
• Breathtaking Scenery: Drive through rolling hills, olive groves, and vineyards, soaking in views that define Tuscany’s charm.
• Flexible & Personal: An exclusive experience for your private group, with the freedom to explore at your own pace.
• Expert Guides & Tastings: Gain insights from knowledgeable drivers and taste the finest local products, including olive oils and balsamic vinegar.

A Deep Dive into the Tuscany Experience

Scenic Comfort from Florence to Chianti

The journey kicks off with a pickup at your Florence accommodation, where you’ll be greeted by a friendly, local driver. The vehicle, an air-conditioned comfort, sets the tone for a smooth ride through Tuscany’s rolling hills. As you leave Florence behind, the landscape shifts into postcard-perfect scenery—cypress-lined roads, lush vineyards, and olive groves stretch out as far as the eye can see. This part of the trip isn’t just transportation; it’s part of the experience, giving you a focus on the breathtaking views that define this region.

San Gimignano: The Towered Medieval Town

Your first stop is San Gimignano, a UNESCO World Heritage site renowned for its skyline of medieval towers. Known as the Town of Fine Towers, it once boasted over 70 towers during its heyday. Today, only 14 remain, standing as a reminder of its past wealth and strategic importance. Walking through its narrow cobblestone streets feels like stepping into a living museum.

You’ll have about an hour to explore, which is enough to soak in the sights, snap photos of the towers, and perhaps indulge in the town’s famous saffron gelato, praised as the best by one reviewer. The town’s quaint shops and historic sites, including the Piazza della Cisterna and the Collegiata Church, offer charming glimpses into medieval life.

The Beautiful Drive to the Wineries

Next, you’ll take a scenic drive along one of Tuscany’s most stunning wine roads. This stretch through the Chianti hills offers panoramic views of lush vineyards, olive groves, and cypress trees. The slow, winding road feels like a genuine journey into Italy’s wine country, setting the perfect mood for the tastings ahead.

Farm Lunch at Podere La Marronaia- Le Colonne

The highlight for many is the farm lunch at a family-run, biodynamic winery. Here, the emphasis on organic, natural production means you’re tasting wines and products made with care and tradition. The farm’s setting is idyllic—tables overlook sweeping vistas of the Chianti hills, creating a perfect backdrop for your meal.

The three courses include homemade pasta, bruschetta, pecorino, extra virgin olive oil, and truffle oil. All dishes are paired with a selection of Tuscan wines, including Chianti Colli Senesi, a Sangiovese-based rosé, and Vernaccia white wine. The inclusion of five different olive oils and balsamic vinegar tastings elevates this experience, allowing you to appreciate the region’s culinary richness. One guest described the lunch as “fabulous,” noting the homemade pasta and generous wine pairings.

Medieval Monteriggioni & Its Fortified Walls

Post-lunch, the tour heads to Monteriggioni, a fortress town founded between 1213 and 1219. Its well-preserved walls and towers make it look like a medieval fortress straight out of a fairy tale. The town’s strategic position made it a formidable defense against Siena, and today, it offers a glimpse into medieval military architecture.

Visitors can explore the castle and visit the medieval weapons museum. The short 30-minute stop allows plenty of time to wander the narrow streets and imagine the town’s history as a defensive outpost.

Final Wine Tasting at Fattoria Lornano

The last stop is at another traditional Chianti winery, Fattoria Lornano. This estate has a long history of wine production, and you’ll get to taste the famous Gallo Nero Chianti Classico alongside other regional wines. This final tasting rounds out the day’s journey, giving you a chance to savor the best of Chianti’s wine-making heritage.

Return to Florence

After this last tasting, you’ll be transported back to your accommodation, ending a day filled with scenic views, authentic wine, and historical exploration.

Is This Tour Right for You?

This experience shines for travelers who want a relaxing, all-in-one day trip with plenty of delicious food and wine. The private group setting means a more intimate vibe, perfect for those who dislike large tours or want personalized attention. The flexible itinerary offers the chance to explore at your own pace, whether that’s lingering in San Gimignano or taking extra time in Monteriggioni.

If your interests include medieval towns, vineyard landscapes, and local culinary specialties, this tour ticks all those boxes. However, if you prefer very structured schedules or are not keen on wine tastings, you might find this laid-back approach less suitable.

Final Thoughts: Is It Worth It?

Considering the $259 price tag, this tour offers significant value—especially when you factor in private transportation, multiple tastings, and a generous farm-to-table lunch. The reviews reinforce this, with one guest describing it as “exceeding all expectations,” praising the guide Stefano for his kindness and knowledge.

The combination of stunning scenery, cultural stops, and authentic Tuscan flavors creates a well-rounded experience for travelers looking to taste and see the best of Chianti in a single day. The fact that the experience is private means you can enjoy a more personalized, relaxed pace—ideal for couples, families, or small groups.

If you’re craving a taste of Tuscany’s enchanting hills, medieval charm, and fantastic wines without the hassle of planning, this tour makes for a fantastic choice.

FAQ

Is pickup included in this tour? Yes, the tour offers pickup from your Florence accommodation, whether it’s a hotel, B&B, or private apartment.

How long is the tour? The entire experience lasts approximately 8 hours, from pickup to return.

Are meals and tastings included? Yes, the tour includes a 3-course Tuscan farm lunch and two wine tastings at different wineries, plus olive oils and balsamic vinegar tastings.

What transportation is used? An air-conditioned vehicle is provided, ensuring comfortable travel throughout the day.

Can I drink all the Chianti I want? While there’s no limit on wine tastings, drinking responsibly is encouraged, especially as you’ll be driving.

Is this tour suitable for children? Most travelers can participate, but wine tastings are intended for adults. Check with the provider if you’re bringing children.

How much time do I have in San Gimignano? About an hour, enough for sightseeing, photos, and maybe sampling saffron gelato.

Are the tours flexible? The itinerary is designed to be relaxed, letting you explore at your own pace within the scheduled stops.

What if I need to cancel? You can cancel up to 24 hours in advance for a full refund.

Is this a private tour? Yes, only your group participates, offering a more intimate experience.

In summary, the “Sweet Hills of Chianti & San Gimignano” tour offers a well-balanced mix of scenic beauty, culture, and gourmet indulgence. It’s best suited for those wanting a stress-free and authentic taste of Tuscany, especially if you’re eager to enjoy private, guided experiences with a focus on wine and food.