Imagine a single, perfect day where the Renaissance genius of Florence gives way to the deep, sun-baked heart of the Tuscan countryside. This tour is an expertly curated journey that threads together the region’s most beloved medieval cities with the intimate, soul-stirring world of its wine production, offering a complete cultural and culinary experience far beyond the standard tourist trail. It is the ultimate opportunity to transition from the urban majesty of Florence to the rolling hills, ancient stone towns, and famed Chianti vineyards that define the global image of Tuscany. The keyword here is immersion: stepping into the landscapes and traditions of Siena and San Gimignano, and culminating in an authentic Winery Lunch that anchors the entire day.

Your adventure begins as the bustling cityscape of Florence fades into a postcard-perfect panorama. The drive itself is part of the experience, winding through the iconic Chianti hills—a tapestry of silver-green olive groves, dark cypress trees standing guard along dusty lanes, and vibrant, regimented vineyards stretching to the horizon. This region is not merely scenery; it is the cradle of Italy’s most famous wines and the historical backdrop for the towns you are about to explore.

The first major stop is Siena, a UNESCO World Heritage site and a city frozen in its glorious medieval past. Here, the unique shell-shaped Piazza del Campo awaits, a masterpiece of civic architecture and the site of the legendary Palio horse race. A local expert will guide you through the city’s highlights, weaving stories of its powerful merchant past and its rivalry with Florence, bringing the rich history of the Palazzo Pubblico and the dramatic black-and-white striped Duomo to life. You’ll have time to wander the narrow, twisting streets—the vicoli—of the city’s historic center, absorbing the atmosphere and discovering hidden fountains and artisanal shops at your own pace. Siena is a vibrant museum, and you are given the space to appreciate its grandeur and its intimate beauty.

From the historical depth of Siena, the journey moves into a truly sensory experience: the Winery Lunch. As the day reaches its midpoint, you are welcomed onto a traditional, family-run Tuscan estate nestled among the vines of the Chianti region. This is the heart of the day’s indulgence. The atmosphere is one of warm, rustic hospitality, where the philosophy is simple: the land provides the finest ingredients, and the table is where they are best enjoyed. The experience begins with a brief introduction to the estate’s wine production, offering insights into the passion and generational knowledge required to create their celebrated vintages.

The main event is the feast—a multi-course traditional Tuscan lunch prepared with fresh, locally-sourced, and often zero food miles ingredients. The table is a generous display of regional specialties designed to perfectly complement the wines. You’ll savor dishes like hearty Ribollita soup or rich truffle lasagna, followed by slow-cooked roasts or another regional main course. Crucially, each course is expertly paired with a generous tasting of the estate’s wines. You will sample the flagship Chianti DOCG, its bolder sibling Chianti Classico Riserva, the highly respected white wine Vernaccia di San Gimignano DOCG, and often a powerful Super Tuscan blend, concluding with the sweet Vin Santo and Cantucci biscuits. This is an education in Tuscan gastronomy, where the history and landscape are tasted on the plate and in the glass, all guided by the convivial presence of the winemakers or a seasoned sommelier.

Finally, the tour leads you to the undisputed crown jewel of the Tuscan hill towns: San Gimignano. Often nicknamed the “Medieval Manhattan” for its astonishing collection of 14 surviving medieval towers, this small walled town presents a skyline unlike any other in Italy. As you stroll through its cobbled streets and the picturesque Piazza della Cisterna, you are transported entirely to the 13th century. You’ll have ample free time to climb one of the towers for a breathtaking view of the surrounding countryside—the very vineyards where your lunch was sourced—or seek out one of the town’s internationally famous artisanal gelaterias.

This day trip is a carefully paced, perfectly balanced blend of history, culture, and cuisine. It removes the stress of navigating the challenging Tuscan roads, allowing you to simply relax and savor the experience. By combining the monumental history of Siena and the fairytale architecture of San Gimignano with the generous hospitality of a Winery Lunch, this tour delivers the full, unforgettable taste of Tuscany in one seamless and enriching day from Florence. It is the perfect itinerary for those seeking to connect with the soul of this legendary region.

Highlights of Siena, San Gimignano and Winery Lunch

• Wander through Siena with free time to explore its stunning Cathedral!
• Tour a charming family-run Chianti winery, with cellar and vineyard visit
• Enjoy 6 wine tastings and a delicious 3-course traditional Tuscan meal
• Discover the magic of San Gimignano’s medieval streets and towers
• Round-trip transportation from Florence in an air-conditioned vehicle

• Round-trip transport from Florence in a climate-controlled vehicle
• Explore Siena with free time to visit the cathedral
• Wine tasting featuring 6 local wines
• Guided winery tour, including cellar and vineyard
• Traditional 3-course Tuscan lunch
• Visit the medieval town of San Gimignano
• Knowledgeable, English-speaking trip leader

• Hotel pick up / drop off
• Entrance fee to Siena’s Cathedral (optional)

.Please arrive 15 minutes early. Meet your guide at Piazzale Montelungo, 50129 Florence. Next to the Piccolo Ristoro kiosk. Look for our friendly staff in red, holding a bright red ‘The Tour Guy’ sign!

Not suitable for

• Wheelchair users

What to bring

• Passport or ID card

Not allowed

• Luggage or large bags

Know before you go

• Please bring sun protection, a bottle of water, comfortable walking shoes, and an empty stomach
• If you have any food allergies or intolerances, please contact us immediately to let us know. We work with our local vendors to plan menus ahead of time so having this information before your tour is important. Please note that there are some occasions where certain allergies cannot be accommodated.
• Please note that the legal drinking age in Italy is 18, we are unable to serve alcoholic beverages to minors.
• DRESS CODE: Entrance into any religious site requires a strict dress code (such as Siena’s Cathedral). Knees and shoulders MUST be covered for both men and women.