Step back in time at the Montalcino Fortress (Fortezza di Montalcino), a majestic sentinel overlooking the rolling hills of Tuscany. Perfect for history buffs and wine lovers alike, this iconic landmark offers breathtaking views of the Val d'Orcia and easy access to world-class Brunello di Montalcino wine tastings. Whether you are exploring medieval architecture on a guided walking tour or indulging in authentic food tours through the charming village, the Fortezza provides an unforgettable gateway to the heart of Italy. Discover the magic of this UNESCO World Heritage region and book your immersive Tuscan experience today!
$165–$455 typical
Median price is $269, with a full range of $69–$679
4.8★ average
Based on 1,966 pooled reviews with 84% positive sentiment
8–11.6 hours typical
Median duration is 11 hours
Wine & Culture
90% are wine tasting tours and 100% cover cultural, food, and historical themes
Free cancellation
100% of options offer free cancellation and instant confirmation
Book ahead
30% of tours are flagged as likely to sell out
4 Products
Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards of Chianti, taste the famed Brunello di Montalcino, and savour local snacks, olive oil and balsamic vinegar – all in a com...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Brunello di Montalcino, widely celebrated as one of the finest wines in the world, is the ultimate expression of a centuries-old winemaking heritage rooted in the passion, dedication, and traditions of the people of Montalcino. Passed down through generations, this remarkable legacy has transformed ...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a wine tasting at a renowned Chianti winery. Optional lunch for an authentic gastronomic experience. Begin your full-day journey by seeing San Gimigna...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and Montepulciano, known for its prestigious Nobile wine. Travel through the UNESCO-listed Val d’Orcia aboard a premium air-conditioned minivan wi...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Landmarks travelers visit on the same route as Montalcino Fortress (Fortezza di Montalcino).