Spend a day tasting boutique wines, savoring regional cuisine, and climbing historic towers in Tuscany’s famed Chianti region with Under The Tuscan Sun Tours. Small group, big flavors, and unforgettable views await.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
8 hours
Fitness Level
Participants should have a basic level of fitness suitable for walking on uneven terrain and climbing stairs.
Wildlife
History
San Gimignano’s medieval Great Tower dates back to the 13th century and was historically built by rival families as a status symbol.
Conservation
Local wineries emphasize sustainable farming practices to protect soil health and preserve the region's natural landscape.
Under The Tuscan Sun Tours
Spend a day tasting boutique wines, savoring regional cuisine, and climbing historic towers in Tuscany’s famed Chianti region with Under The Tuscan Sun Tours. Small group, big flavors, and unforgettable views await.
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 Shoes
The tour involves walking on uneven surfaces at wineries and climbing the Great Tower in San Gimignano, so sturdy, comfortable footwear is recommended.
Stay Hydrated
Bring a water bottle to stay hydrated between tastings, as wine sampling can be dehydrating.
Inform About Dietary Restrictions
Under The Tuscan Sun Tours accommodates allergies and special dietary needs—notify in advance to ensure a tailored lunch experience.
Don't Forget Your Camera
Capture panoramic vistas and the medieval architecture of San Gimignano for a lasting memory of your Tuscan adventure.
Comfortable Walking Shoes
Necessary for vineyard paths and tower climbs where uneven footing is common.
Sunscreen
Protect skin during open-air activities especially in sunny conditions.
spring
Light Jacket
Useful for cool mornings and evenings in Chianti and San Gimignano.
fall
Water Bottle
Keep hydrated during wine tastings and walking segments.
summer