Tuscan Food & Wine Tour with Under The Tuscan Sun

Read the full experience

Set against the rolling hills of Tuscany, Under The Tuscan Sun Tours offers an immersive 8-hour journey through the renowned Chianti wine region, starting from Piazza di Verzaia in Florence. This shared small-group experience, capped at eight guests, uncovers authentic flavors and historic charm through two boutique wineries known for crafting exceptional vintages amid the classic vineyards of Chianti. Guests move beyond the usual tourist trail, sampling over ten distinct wines paired with a carefully prepared lunch that reflects regional culinary traditions. The tour seamlessly blends outdoor immersion with cultural discovery, taking travelers next to San Gimignano, a striking medieval town perched atop Tuscan hills. Here, the opportunity to climb the Great Tower rewards adventurers with sweeping views of the surrounding landscape dotted with olive groves and cypress-lined roads. The visit culminates with a taste of San Gimignano’s acclaimed gelato, often crowned world champion, a sweet contrast to the robust wines enjoyed earlier. Under The Tuscan Sun Tours stands out in Florence’s outdoor recreation scene by combining active exploration with curated culinary experiences tailored for small groups. This approach allows participants to engage deeply with the terroir, heritage, and hospitality that define this part of Tuscany. The company’s intimate pricing and detailed itinerary ensure travelers will walk away with a rich understanding of Chianti’s geography, winemaking craft, and medieval artistry. Whether you’re an enthusiast seeking regional authenticity or a casual traveler craving a day of sensory pleasures, this food and wine tour offers a distinctive window into Tuscany’s layered landscape and living history.

Trip highlights

Difficulty

moderate.

Duration

8 hours.

Fitness level

Participants should have a basic level of fitness suitable for walking on uneven terrain and climbing stairs.

Frequently asked questions

How many people are on the tour?

The tour is designed for small groups, with a maximum of 8 participants to ensure a personalized experience.

Is lunch included in the tour?

Yes, lunch is included at the second winery, featuring regional cuisine paired with wines.

Can you accommodate dietary restrictions?

Yes, Under The Tuscan Sun Tours accepts special dietary requests and allergies if notified in advance.

What kind of walking is involved?

Moderate walking on uneven vineyard terrain and climbing stairs in San Gimignano’s Great Tower.

Where does the tour start and end?

The meeting point is Piazza di Verzaia, 2 in Florence’s San Frediano district, where the tour both starts and concludes.

Is transportation provided between stops?

Yes, transportation between wineries and San Gimignano is included as part of the guided tour.

Local insights

Wildlife

European hare
various songbirds common in Tuscan hills

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.

About Under The Tuscan Sun Tours

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.

Base locationFirenze, Toscana

Tours offered161+

Specialtyothers

Adventure tips

Wear Comfortable ShoesThe tour involves walking on uneven surfaces at wineries and climbing the Great Tower in San Gimignano, so sturdy, comfortable footwear is recommended.

Stay HydratedBring a water bottle to stay hydrated between tastings, as wine sampling can be dehydrating.

Inform About Dietary RestrictionsUnder The Tuscan Sun Tours accommodates allergies and special dietary needs—notify in advance to ensure a tailored lunch experience.

Don't Forget Your CameraCapture panoramic vistas and the medieval architecture of San Gimignano for a lasting memory of your Tuscan adventure.

Recommended gear

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.
Light Jacket: Useful for cool mornings and evenings in Chianti and San Gimignano.
Water Bottle: Keep hydrated during wine tastings and walking segments.