THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Join a small group tour from Florence to experience Tuscany’s rich history, savor award-winning Chianti wines, and explore the medieval streets of San Gimignano. Discover why this region is a must-visit for wine lovers and history buffs alike.
Join a small group tour from Florence to experience Tuscany’s rich history, savor award-winning Chianti wines, and explore the medieval streets of San Gimignano. Discover why this region is a must-visit for wine lovers and history buffs alike.
Book with Under The Tuscan Sun Tours
Verified experiences and guided adventures in the surrounding area.
Operated by Under The Tuscan Sun Tours · Florence, Florence
In the rolling hills of Tuscany, the town of Florence serves as a starting point for a journey into the region’s rich history, vibrant culture, and world-renowned gastronomy. Under The Tuscan Sun Tours offers a 6-hour shared small group experience that immerses you in the very heart of Tuscany’s iconic landscape. As your group of up to eight travelers departs Florence, the scenery shifts from bustling city streets to scenic vineyards, olive groves, and ancient stone towns. The first highlight is San Gimignano, a UNESCO World Heritage site famous for its medieval skyline studded with soaring towers. Climbing the Great Tower offers sweeping views over the surrounding countryside, while wandering its cobblestone streets reveals centuries of history and local artisanship. Lunch is a highlight, with a regional feast paired with tastings at a premier Chianti winery. Here, you can sample award-winning wines crafted from grapes grown in the AD-18th-century vineyards, complemented by local cheeses and fresh pasta. Afterward, a visit to a nearby vineyard allows you to savor traditional winemaking techniques, making this trip a perfect blend of cultural immersion and culinary delight. This tour is designed to give a genuine taste of Tuscany's storied past and vibrant present, giving visitors a chance to relax, learn, and indulge amidst some of Italy’s most iconic scenery. Whether you're a seasoned wine connoisseur or a curious traveler, the intimate group setting and expert guides make this experience both educational and enjoyable. It’s an ideal day for those looking to see the historic sights, sample remarkable wines, and enjoy the timeless charm of Tuscany in a relaxed, friendly atmosphere.
No, guides will explain the wine tasting process and regional varieties to all participants.
Yes, a traditional Tuscan lunch is provided, paired with local wines.
The tour operates in small groups of up to 8 people for a personalized experience.
Yes, but the experience is best suited for ages 12 and up due to walking and tasting activities.
It involves some walking and climbing stairs but is suitable for most able-bodied travelers.
Yes, please notify the tour operator in advance for special dietary needs.
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