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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
9 hours
Fitness Level
Suitable for all fitness levels; includes short hikes and walking on uneven terrain.
Wildlife
History
Val d’Orcia’s status as a UNESCO World Heritage site stems from its Renaissance-era agricultural landscape and impeccably preserved medieval villages.
Conservation
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
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.
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.
Location
Florence, Tuscany
Headquartered in historic Florence
Group Size
Up to 8 (shared)
Small-group tour options available
Shore Excursions
Livorno & La Spezia
Private shore pickups offered
Featured Tours
Pisa, Chianti, 5 Terre
Iconic Tuscany destinations covered
Reserve a shore excursion or Florence tour today: private vehicles, experienced guides, and curated wine and cultural itineraries ready for booking.
Wear Comfortable Walking Shoes
Medieval streets and fortress grounds require sturdy, comfortable footwear for manageable hiking and walking.
Stay Hydrated Throughout the Day
Bring a water bottle to stay refreshed, especially during the extended walking sessions between tastings.
Book Early for Private Group Tours
Ensure availability and personalized service by reserving your spot well in advance.
Bring a Camera for Scenic Views
Capture panoramic landscapes from the Montalcino fortress and the charming streets of Pienza.
Comfortable Walking Shoes
Necessary for navigating cobblestone streets and fortress paths.
Reusable Water Bottle
Staying hydrated during tastings and walking is important.
summer|spring|fall
Sun Protection
Bring sunscreen, sunglasses, and a hat for sun exposure during outdoor segments.
summer|spring|fall
Light Jacket or Layered Clothing
Temperatures can vary, especially in mornings and evenings.
spring|fall|winter