THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Discover Tuscany’s famed vineyards, medieval towns, and historic sites on a full-day private wine and cultural tour with Under The Tuscan Sun Tours. Taste, climb, and savor your way through Siena, Chianti, San Gimignano, and Florence’s iconic viewpoints.
Discover Tuscany’s famed vineyards, medieval towns, and historic sites on a full-day private wine and cultural tour with Under The Tuscan Sun Tours. Taste, climb, and savor your way through Siena, Chianti, San Gimignano, and Florence’s iconic viewpoints.
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Verified experiences and guided adventures in the surrounding area.
Operated by Under The Tuscan Sun Tours · Florence, Tuscany
Set your sights on Tuscany, Italy’s rolling heartland where medieval architecture meets sun-drenched vineyards. Under The Tuscan Sun Tours offers a private, nine-hour journey weaving together history, local flavor, and landscape in a seamless story. This tour invites travelers to start in Florence before diving deep into the iconic sights and tastes of Siena, Monteriggioni, San Gimignano, and Chianti's famed vineyards.
The day begins with a pick-up right at your address in Florence, easing you into the pace of Tuscan life. First stop: Siena. Known for its well-preserved Gothic grandeur, Siena’s Duomo commands attention with its striking striped marble facade and intricate interior mosaics. A climb up the Duomo’s terraces rewards you with a commanding view of the city’s winding streets and the Campo, the historic square home to the Palio horse race, a centuries-old tradition pulsating with local pride.
Next, the tour rolls into the Chianti region, where the landscape transitions into a peaceful patchwork of grapevines and olive groves. Here, lunch is more than a meal — it’s an immersion. Savor traditional Tuscan dishes paired with estate-produced wines and olive oils at a boutique winery, an experience emphasizing terroir and tradition.
Afternoon brings the medieval charm of San Gimignano into focus. Famous for its soaring towers, climbing the Great Tower offers panoramic vistas of the surrounding countryside. Don’t miss a tasting of the village’s award-winning gelato — a sweet contrast to the robust reds of the vineyard.
The finale unfolds at Michelangelo Plaza, just outside Florence, where sweeping views of the city’s rooftops and the Arno River create a perfect closing tableau. Under The Tuscan Sun distinguishes itself by blending expert local knowledge with seamless private transport, ensuring each moment is rich and relaxed. This tour is far more than sightseeing—it’s a paced immersion into Tuscany’s soul, perfect for those who appreciate culture, cuisine, and landscape in equal measure.
easy.
9 hours.
Suitable for most adults with basic walking ability and no mobility impairments
Yes, this is a private VIP tour, designed for your group alone with a dedicated driver-guide.
Absolutely. Let Under The Tuscan Sun Tours know in advance to customize your lunch.
Moderate walking includes city streets and climbing the Duomo and San Gimignano’s towers.
The driver-guide speaks English to provide rich cultural insights throughout the tour.
Yes, private transportation from your Florence address and back is included.
While the tour follows a set itinerary, special requests may be possible when arranged in advance.
Siena’s Palio horse race dates back to medieval times, a deeply rooted local tradition held in the Campo square.
Many wineries in Chianti practice sustainable viticulture to preserve the landscape and biodiversity.
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