Immerse yourself in the rolling hills of the Val d'Orcia with an unforgettable journey to Montalcino. As a jewel of the Tuscan countryside and a UNESCO World Heritage region, Montalcino invites you to indulge in world-class Brunello di Montalcino wine tastings, authentic food tours, and breathtaking sightseeing adventures. Whether you are exploring historic hilltop fortresses on a guided walking tour or enjoying a private wine experience, our curated selection of 87 top-rated activities ensures a perfect escape. Discover the soul of Italy through its rich culture, stunning landscapes, and unparalleled culinary traditions. Book your Tuscan dream today!
$162–$696 typical
Median price is $323, with a full range of $79–$1,216
4.82★ average
Based on 4,010 pooled reviews with ~90% positive sentiment
5–11 hours typical
Median duration is 9 hours
Wine & Food
83% are wine tasting tours and 84% focus on food and drinks
51% private tours
79% of options are guided, with 85% offering free cancellation
8 languages offered
Includes EN, IT, ES, FR, PT, ZH, DE, and KO
44 Products
Tour the Montalcino hill, visit the town and three different Brunello wine producing wineries. Tour cellars, meet the producers, enjoy wine tastings and a winery lunch with wine.
Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive a tour of an organic dairy farm followed by a cheese tasting. Visit the beautiful Renaissance gem that is the hilltown of Pienza and enjoy lun...
For a full refund, cancel at least 24 hours before the scheduled departure time.
This is a semi- private with maximum 6 people in tour so you will have all the attention you need. This tours will give you the advantages to truly enjoy the experience and not have to be in a crowded bus and follow a strict schedule . We will visit 2 beautiful boutique family owned wineries in a ...
For a full refund, cancel at least 24 hours before the scheduled departure time.
* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small wineries for private visit and wine tastings * 8 hours * Very knowledgeable English speaking local driv...
All sales are final. No refund is available for cancellations.
This is a semi-private which means a maximum of 6 people in tour, so you will have a private vehicle and all the attention you need to enjoy your trip with a five-star service. This experience will give you the advantages to truly enjoy the tour instead of the big bus tours where you have to follow ...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Our driver guide will collect you at the designated meeting point, setting off toward Montalcino. Start this full-day tour with a lesser-known boutique vineyard with high-quality wines. You will taste all their full-bodied Brunello reds that make this region every wine lover’s dream. After your ...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Escape into the rolling hills of Tuscany and discover the beauty of Val d’Orcia. Taste Brunello wine, explore Pienza, Montalcino, and enjoy a traditional lunch at a local winery.
Immerse yourself in the beauty of Italian Tuscany on this tour of the Chianti Valley from Siena. Explore San Gimignano & Montalcino and taste local wines!
Free cancellation up to 24 hours before the activity starts. Any cancellations after this or no-shows on the day will not be refunded.
Spend a day in the Tuscan countryside and discover the charms of medieval San Gimignano, Chianti, and Montalcino. Enjoy a wine tasting in a prestigious Chianti winery. Join an optional lunch.
Discover the charming towns of San Gimignano and Montalcino on a small group day trip from Siena. Visit a part of Val d'Orcia and a Chianti winery to taste the famous Chianti wines with local products
Landmarks travelers visit on the same route as Montalcino.
