THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Spend a day in Tuscany savoring traditional Chianti wines and gourmet Tuscan cuisine before indulging in luxury shopping at Florence's exclusive Fashion Valley. Discover the perfect mix of heritage and high-end style.
Spend a day in Tuscany savoring traditional Chianti wines and gourmet Tuscan cuisine before indulging in luxury shopping at Florence's exclusive Fashion Valley. Discover the perfect mix of heritage and high-end style.
Book with Under The Tuscan Sun Tours
Verified experiences and guided adventures in the surrounding area.
Operated by Under The Tuscan Sun Tours · Florence, Tuscany
Set against the rich backdrop of Tuscany, the Chianti Wine & Shopping Tour offers an immersive eight-hour journey beginning in Florence, Italy’s cradle of Renaissance art and culture. This experience merges the region’s renowned viticulture with upscale shopping, all framed by stunning medieval and modern vistas. Your day begins with a scenic drive to the medieval town of San Gimignano, where ancient stone towers punctuate the skyline, offering a glimpse into Tuscany’s storied past. Here, locals still practice centuries-old winemaking traditions, and you'll enjoy a lunch featuring authentic Tuscan cuisine paired with organic Chianti wines from family-run vineyards. After satisfying your palate, the tour shifts gears to the Fashion Valley, an exclusive shopping destination boasting high-end brands like Prada and Gucci. This blend of rustic charm and contemporary luxury makes the experience distinctive, showcasing Tuscany’s dual identity as both a bastion of heritage and a trendsetter. The tour culminates with panoramic views of Florence’s skyline at sunset, immortalizing the contrast between the city’s historic domes and its modern vibrancy. What sets this tour apart is its seamless integration of lifestyle, history, and luxury—far beyond the typical day trip. Whether you’re a wine enthusiast, a fashion aficionado, or simply curious about Tuscany’s diverse appeal, this tour enriches your visit with flavorful stories and elite shopping. Florence, as the nearby city hub, provides an exceptional setting, making this combined itinerary a unique way to taste, shop, and savor the best of the region in one unforgettable day.
moderate.
8 hours.
Suitable for individuals comfortable with walking moderate distances over varied terrain and standing during tastings and shopping.
Yes, a traditional Tuscan lunch with organic wine tasting is part of the experience.
Please inform the operator in advance so they can tailor the meal to your needs.
No, shopping is at your own expense at the Fashion Valley mall.
Expect moderate walking between sites and through shopping areas, suitable for most fitness levels.
Spring and fall offer pleasant weather conditions for both outdoor visits and shopping.
Yes, transportation between Florence, San Gimignano, and Fashion Valley is included.
San Gimignano’s medieval towers date back to the 12th century, reflecting the town’s historical wealth and strategic importance.
Many local vineyards practice organic farming to protect Tuscany’s delicate soil and preserve traditional winemaking methods.
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