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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.
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.
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Verified experiences and guided adventures in the surrounding area.
Operated by Under The Tuscan Sun Tours · Florence, Florence
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.
easy.
6-7 hours.
Guests should be comfortable walking moderate distances
Yes, transportation between Florence, San Gimignano, and the winery is arranged by the tour operator.
Absolutely, non-alcoholic options and alternative activities are available; please inform the guide beforehand.
Multiple tastings are included, but portions are small, allowing you to enjoy without overindulgence.
Casual, comfortable clothing is appropriate, with layers recommended for variable weather.
Children are welcome, but the experience is geared towards adults; please check with the tour operator for specific policies.
Approximately a 1-hour drive, making this a convenient day trip from the city.
San Gimignano's famous towers once served as symbols of wealth and power among medieval noble families.
Many wineries prioritize sustainable practices, using organic methods and reducing water waste to protect Tuscany’s landscapes.
Under The Tuscan Sun Tours is a Florence-based tour operator specializing in private and small-group experiences across Tuscany and nearby regions. Founded to connect visitors with the cultural, culinary and scenic highlights of central Italy, the company offers a wide range of day trips, shore excursions and immersive activities. Operating from Florence, Tuscany, the catalogue includes private VIP shore excursions from Livorno, La Spezia and Piombino to destinations such as Pisa, Lucca, Florence, Cinque Terre, San Gimignano and the Chianti wine region. Options span guided walking tours with reserved entries (Uffizi, Accademia), winery visits with tastings and meals, truffle hunting with trained dogs, cooking classes, Vespa tours and curated visits to Bolgheri for Supertuscan wine tastings. Services include private vehicles and professional drivers for full-day transfers, small shared tours for groups up to eight people, and tailored itineraries for families or wine enthusiasts. Specific shore excursions list included stops, tasting experiences and local activities, while other experiences emphasize cultural sites such as Michelangelo’s David, the Duomo, and Carrara marble quarries. Under The Tuscan Sun Tours works with licensed local guides and established wineries, restaurants and activity providers to deliver organized itineraries and reserved accesses. The business emphasizes clear pickup arrangements from ports (Livorno, Piombino, La Spezia) and from central Florence, offering a practical way to turn limited time into a full Tuscan experience.
Book with Under The Tuscan Sun Tours