Is transportation included?

Yes, transportation between Florence, San Gimignano, and the winery is arranged by the tour operator.

Can I participate if I don’t drink alcohol?

Absolutely, non-alcoholic options and alternative activities are available; please inform the guide beforehand.

How much wine is typically tasted?

Multiple tastings are included, but portions are small, allowing you to enjoy without overindulgence.

Is there a dress code?

Casual, comfortable clothing is appropriate, with layers recommended for variable weather.

Are children allowed?

Children are welcome, but the experience is geared towards adults; please check with the tour operator for specific policies.

How far is San Gimignano from Florence?

Approximately a 1-hour drive, making this a convenient day trip from the city.

Tuscany Wine and Medieval Town Tour with Under The Tuscan Sun Tours | Winery

Adventure Brief

Join Under The Tuscan Sun Tours on a full-day journey through Tuscany’s historic towns, vineyards, and culinary delights. Discover San Gimignano’s medieval charm and indulge in wine and olive oil tastings at a renowned Chianti winery, topped off with a gourmet dinner. Experience the heart of Italy’s wine country in an intimate small-group setting.

6-7 hours

easy

From €189.82

Set against the rolling, sun-drenched hills of Tuscany, Florence serves as the perfect starting point for a day of immersive wine tasting, historic charm, and culinary delights. Under The Tuscan Sun Tours offers an engaging full-day experience that takes small groups—up to eight travelers—on a journey into Italy’s renowned wine country. The adventure begins with a visit to San Gimignano, a medieval town famed for its iconic skyline of towers piercing the sky, a living reminder of Tuscany’s rich history. Wandering its narrow streets, visitors get a taste of centuries past, with well-preserved architecture and local artisan shops providing a captivating backdrop.

After soaking in the town’s timeless atmosphere, the tour transitions to the countryside, where a top-tier Chianti winery awaits. Here, guests enjoy tastings of award-winning wines paired with olive oils, learning about the region’s centuries-old winemaking traditions. As the day progresses, the group indulges in a hearty Tuscan dinner at the winery, featuring local specialties crafted with ingredients sourced from the surrounding land. Throughout the experience, camaraderie blossoms as travelers share stories amid vineyard vistas bathed in the golden glow of afternoon light.

This tour isn't just about tasting wine; it’s an opportunity to connect with Tuscany’s culture and landscape in a relaxed, intimate setting. Under The Tuscan Sun Tours excels at blending genuine local experiences with comfort, making it a standout choice for those seeking a memorable taste of Italy’s culinary and historic scene. The combination of vibrant towns, lush vineyards, and delicious cuisine offers a well-rounded immersion into the region’s essence, perfect for first-time visitors or seasoned travelers alike.

Whether you're a wine enthusiast, history buff, or food lover, this full-day adventure makes for an authentic inside look at Tuscany’s famed countryside—all with expert guides ensuring a seamless and engaging day out. It’s not just a tour; it’s an encounter with the enduring spirit of Italy’s most beloved region.