easy
6–8 hours
Suitable for most visitors with average fitness; moderate walking between sites required.
Travel through Tuscany’s historic heart with Under The Tuscan Sun Tours. From Siena’s cathedral to Chianti wines and San Gimignano’s towers, this private journey offers an authentic Italian escape.
In the heart of Tuscany, just outside Florence, Under The Tuscan Sun Tours offers a private VIP journey that threads through centuries of rich history, rolling vineyards, and fortified hilltop towns. This exclusive experience invites travelers to follow the footsteps of medieval artisans and winemakers across iconic landscapes where time seems to slow.
The tour begins in Siena, a city defined by its Gothic cathedral and the famed Piazza del Campo, site of the legendary Palio horse race. Walking these ancient streets offers a rare glimpse of history carved in stone and communal pride. From there, the path leads to Monteriggioni, a small medieval fortress whose imposing walls stand as a unique emblem of Tuscan defense architecture, perched high above undulating hills.
But no Tuscan escapade would be complete without tasting its celebrated Chianti wines. Guests are welcomed into a renowned vineyard to savor signature blends crafted from Sangiovese grapes, pairing them with handcrafted local cheeses and cured meats. The wine's bright cherry notes and earthy depth mirror the landscape's rugged charm.
The tour’s finale lies in San Gimignano, known as the Medieval Manhattan for its preserved tower skyline. Here, visitors enjoy a taste of the town’s renowned gelato before unwinding in its winding alleys rich with artisan shops and Romanesque churches.
Under The Tuscan Sun Tours stands out for its intimate, tailored approach, delivering access to hidden corners often missed by larger groups. It’s a perfect balance of history, culture, and culinary delight framed by Tuscany’s striking natural beauty. Whether you’re a history buff, a wine enthusiast, or a traveler hungry for authentic Italian experiences, this tour captures the essence of Tuscany beyond the postcards.
This private tour is popular and limited; advance booking ensures availability and personalized experience.
Expect cobblestone streets and uneven terrain in medieval towns, so sturdy walking shoes are recommended.
Bring a water bottle, especially during summer, as you’ll be walking between historic sites and vineyards.
Early visits to Siena and Monteriggioni avoid crowds and offer the best natural light for photos.
Monteriggioni’s fortress dates back to the early 13th century, built as a defensive bulwark during the conflicts between Siena and Florence.
The region promotes sustainable viticulture practices to preserve both soil health and traditional farming methods critical to Chianti’s character.
Necessary for navigating cobblestone streets and vineyard paths comfortably.
Weather can change rapidly; layering keeps you comfortable indoors and outdoors.
spring|fall|winter specific
Staying hydrated during the tour, especially during warmer months, is important.
summer|spring|fall specific
Capture the striking medieval architecture, vineyards, and Tuscan landscapes.