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Spend a day tasting Brunello wines and Pecorino cheese amid the rolling hills of Tuscany’s Val d’Orcia. Under The Tuscan Sun Tours offers a private, in-depth journey through Montalcino’s fortress and Pienza’s cobbled streets.
Spend a day tasting Brunello wines and Pecorino cheese amid the rolling hills of Tuscany’s Val d’Orcia. Under The Tuscan Sun Tours offers a private, in-depth journey through Montalcino’s fortress and Pienza’s cobbled streets.
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Verified experiences and guided adventures in the surrounding area.
Operated by Under The Tuscan Sun Tours · Florence, Tuscany
The Val d'Orcia region of Tuscany stands apart for its sweeping hillscapes, golden fields, and timeless villages—an unspoiled cultural landscape protected by UNESCO. Under The Tuscan Sun Tours offers a distinct opportunity to experience this legendary area beyond the typical sightseeing, with their Private VIP Brunello & Pecorino Wine & Cheese Tour. This 9-hour journey unfolds across two emblematic towns: Montalcino and Pienza, each celebrated for their culinary and historic appeal.
The day begins with a pick-up directly at your accommodation in or near Florence, whisking you into the heart of the Val d'Orcia region. Montalcino commands attention with its medieval fortress perched atop a hill, where rugged stone walls meet panoramic views of vineyards and olive groves stretching to the horizon. Here, you’ll hike the fortress grounds before stepping into intimate wine shops and renowned wineries dedicated to Brunello di Montalcino, one of Italy’s most prestigious red wines. A private tasting session offers the chance to savor the deep, complex notes that give Brunello its reputation.
Following a scenic drive through the patchwork of Tuscany’s rolling hills, the tour continues to Pienza. This Renaissance village, recognized for its harmonious architecture and perfectly preserved palace facades, is the cradle of Pecorino cheese traditions. Sampling fresh and aged Pecorino varieties is more than a tasting—it’s a way to connect with the region's agrarian heritage.
Under The Tuscan Sun Tours stands out by coupling cultural immersion with private and comfortable transportation, guided by knowledgeable English-speaking drivers who tailor the experience for small groups (up to eight). The itinerary respects your pace, balancing walking in historic sites with leisurely tastings and ample time to absorb Tuscany’s vistas.
For travelers passionate about food, wine, and authentic regional customs, this tour offers a full-day dive into Tuscany’s heart—rich in tradition, taste, and terrain. Its seamless blend of outdoor recreation, cultural history, and gastronomic pleasure makes this experience a distinct anchor for any visit to the area.
easy.
9 hours.
Suitable for all fitness levels; includes short hikes and walking on uneven terrain.
Yes, private transportation with an English-speaking driver is included for the duration of the tour.
No, meals are not included, but the guide will recommend excellent local restaurants for lunch.
The tour accommodates up to eight people per van to ensure an intimate experience.
The tour is generally accessible, but there is some walking on uneven terrain; please consult the operator if you have specific concerns.
As a private experience, there is flexibility—contact Under The Tuscan Sun Tours directly to discuss options.
Comfortable shoes, weather-appropriate layered clothing, sun protection, and a camera are recommended.
Val d’Orcia’s status as a UNESCO World Heritage site stems from its Renaissance-era agricultural landscape and impeccably preserved medieval villages.
Local wineries and farms actively engage in sustainable practices to preserve soil quality and biodiversity while maintaining traditional artisan 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