easy
8 hours
Moderate walking ability recommended—comfortable with stairs and uneven surfaces.
Spend a day touring Tuscany’s organic vineyards and savoring authentic flavors with Under The Tuscan Sun Tours. Traverse medieval San Gimignano’s ancient streets and enjoy exclusive tastings of wine and olive oil in Chianti’s sunlit hills.
Tuscany’s rolling hills unfurl beyond Florence, weaving a route rich with organic vineyards, historic hill towns, and some of Italy’s most treasured culinary experiences. Under The Tuscan Sun Tours invites travelers to step into this landscape through an immersive, private VIP experience: an 8-hour journey tasting organic wines and olive oils, climbing medieval towers, and savoring authentic flavors. Starting just outside Florence, this tour carves a path through Chianti’s sweeping vineyards where sustainable farming practices yield complex wines and award-winning olive oils. The focus on organic agriculture isn’t just environmental—it strikes a delicious balance in every sip and bite, revealing the region’s Terra Madre at its purest.
The trip’s urban anchor is San Gimignano, a striking medieval town whose stone towers punctuate sky and story alike. Guests ascend the Great Tower for panoramic views that stretch across Cyprus groves, olive orchards, and vineyards to the distant Apennines. Time here is not hurried; wandering cobblestone streets rewards curiosity with artisan shops and the chance to sample Italy’s iconic gelato—an essential ritual after scaling the heights.
The finale at Michelangelo Square in Florence offers unrivaled views over the Arno River, the Duomo’s terracotta dome, and distant Tuscan hills, creating a photographic crescendo. Under The Tuscan Sun Tours specializes in crafting personalized journeys that connect travelers deeply to the region’s authentic landscapes and culinary heritage. This tour is ideal for those who want a hands-on understanding of Tuscany’s organic food culture fused with cultural discovery—far beyond the usual tourist routes. It’s a meeting of history, nature, and taste that invites reflection and appetite in equal measure.
This VIP tour is highly personalized and best reserved ahead of time to secure your preferred date and ensure an intimate experience.
Prepare for walking on uneven cobblestones and stairs, especially when climbing San Gimignano’s Great Tower.
Tuscany’s sun can be strong, even in spring and fall, so bring water to stay refreshed between tastings and excursions.
Engage with winemakers and guides to deepen your connection with organic farming practices and local culinary traditions.
San Gimignano’s towers were built by noble families during the Middle Ages as symbols of wealth and power, offering a glimpse into feudal Tuscan life.
Organic farming in Chianti supports soil health and biodiversity, reflecting Tuscany's growing dedication to sustainable agriculture and preserving its rural landscape.
Necessary for navigating cobblestone streets and vineyard terrain comfortably.
Useful in case of sudden showers common during cooler seasons.
spring|fall|winter specific
Protects you from the strong Tuscan sun while enjoying outdoor tastings.
summer specific
Keeps you hydrated throughout the long day of touring and tasting.