Tuscan Wine Tours & San Gimignano with Under The Tuscan Sun - Florence

Tuscan Wine Tours & San Gimignano with Under The Tuscan Sun

Florencemoderate

Difficulty

moderate

Duration

8 hours

Fitness Level

Participants should be comfortable standing, walking on uneven surfaces, and climbing stairs for several hours.

Overview

Spend a day outside Florence savoring Tuscan wine, climbing San Gimignano’s towers, and tasting authentic local flavors with Under The Tuscan Sun Tours. This private trip offers a rich blend of culture, scenery, and gastronomy in Chianti’s iconic landscape.

Details

Beneath the sun-drenched skies of Tuscany, just a short drive from Florence, Under The Tuscan Sun Tours offers a tailored journey through the heart of the Chianti region. Their Private VIP – BUONGIORNO CHIANTI! experience condenses the essence of Tuscany into a single immersive day. This isn’t just about ticking off sights; it’s a curated passage that immerses travelers into centuries-old landscapes where vineyards arch across rolling hills, medieval towns rise from stone, and flavors tell stories as rich as the land itself. The day begins with a visit to San Gimignano, a striking medieval hill town famed for its skyline of intact towers, relics of a once fiercely competitive merchant rivalry. Climbing the Great Tower rewards travelers with panoramic views over the surrounding countryside, punctuated by olive groves and vineyard rows stretching to the horizon. Just as memorable is the chance to savor award-winning gelato from a local vendor, a sweet marker of place and tradition.

Two distinctive wineries open their doors next, providing more than a tasting but an education in Chianti’s signature Sangiovese grapes and artisanal vinification techniques. Each pour comes paired with stories of terroir, land stewardship, and family heritage, making every sip a deeper connection to the region. Between tastings, guests enjoy a carefully prepared Tuscan lunch that spotlights seasonal, local produce against breathtaking vineyard views, making every moment a feast for both palate and eyes.

Under The Tuscan Sun Tours stands out for their personalized, no-crowd approach. This private tour provides exclusive access often missed by standard group offerings, blending history, nature, and gastronomy in a seamless day that champions Tuscany’s outdoor beauty and cultural richness. This experience invites travelers to step off the beaten path, into an authentic taste of Tuscany’s famed landscape and lifestyle.

Adventure Tips

Wear comfortable shoes

San Gimignano’s cobblestone streets and tower climb require sturdy, comfortable footwear for ease and safety.

Bring a bottle of water

Stay hydrated throughout the day, especially during summer tastings and walks in the sun.

Check for dietary preferences in advance

Inform the tour company of any allergies or dietary restrictions to ensure lunch accommodates your needs.

Be ready for moderate physical activity

The experience includes walking, standing during tastings, and climbing narrow towers, so a moderate fitness level is advised.

Local Insights

Hidden Gems

  • Piazza della Cisterna in San Gimignano – a lively square with historic wells and local artisans.
  • Less-traveled hillside vineyard trails around Chianti for quiet hiking views.

Wildlife

  • European kestrel soaring above vineyards.
  • Wild boar tracks sometimes visible on forest edges.

History

San Gimignano’s towers date back to medieval rival families competing for status and defense, resulting in its unique skyline.

Conservation

Chianti wineries often embrace sustainable and organic farming practices to maintain soil health and support regional biodiversity.

Frequently Asked Questions

Photography Tips

Best Times

Early morning
Golden hour
Late afternoon

Best Viewpoints

  • Top of San Gimignano’s Great Tower
  • Vineyard terraces overlooking rolling hills
  • Tuscan countryside roads flanked by cypress rows

What to Photograph

Medieval towers
Vineyard landscapes
Rustic Tuscan lunch settings

Recommended Gear

Comfortable walking shoes

Essential

Necessary for navigating both cobbled streets and vineyard terrain.

Sunhat and sunscreen

Essential

Protect yourself from sun exposure during daytime outdoor tastings.

spring specific

Light rain jacket

Useful in case of unexpected showers during springtime.

spring specific

Reusable water bottle

Essential

Stay hydrated during long tasting sessions and walking tours.

summer specific

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