Top Siena Holidays

Sample Italy's flagship Brunello di Montalcino wine in the hills where it’s produced with this exclusive winery tour and tasting at a medieval castle. Join a sommelier for a stroll through the vineyards to learn about the history and production of Brunello at this family-run estate, then relax over a tasting that pairs three different wines with local specialties. Cap off your experience with a three-course Tuscan lunch.

Tuscany is world-renowned for its wine, so ensure you get an insider’s glimpse into the industry during a tasting tour of the vineyards surrounding Siena. Receive personalized attention in a small group limited to 12 as you visit a historical cellar and educate your palate to recognize subtle flavors with the help of a sommelier. Plus, a choice of morning or afternoon departure means you can slot this tour into even the busiest of sightseeing schedules.

Take a tour of Siena with a local, and get the lowdown on the city that the guidebooks can’t give. In a small group that’s limited to just ten people, you’ll explore Siena by foot to discover the history behind the UNESCO-listed Piazza del Campo and its nearby monuments, and sample classic food from Tuscany with Chianti wine.

Take the stress out of planning a day in Tuscany on this half-day small-group tour of the Chianti wine region from Siena, including transport. Enjoy an air-conditioned ride over to two popular wineries to taste wines and oils locals love. Plus spend some free time in Monteriggioni, and catch a glimpse of the town’s well-known medieval castle.

Spend an afternoon in the wine town of Montalcino, tasting the prestigious Brunello di Montalcino and learning about wine production. This tour from Siena that tasting of local wine paired with salami and cured meat. Admire views of the Tuscan countryside from the pretty hill town and discover the region’s generations-old winemaking traditions.

Take your Tuscan wine tasting to the next level with this one-of-a-kind experience set in an authentic medieval aqueduct hidden below the historic city center. Settle in among brick vaults and tunnels dug directly into the stone to sip a selection of Brunello di Montalcino and Super Tuscan wines from the vineyards of Siena and Chianti, paired with local cheese.

Explore some of the most popular Tuscan hill towns on this day trip to Siena, San Gimignano, and Monteriggioni from Florence. Enjoy visiting each town independently while also having the round-trip transportation organized in advance. Learn about the famous region from the tour leader on board the bus, listening to informative commentary as you travel.

Taste your way through Tuscany with this full-day wine tour of Pienza and Montepulciano from Siena. Visit the charming town of Pienza and stop for one wine tasting each in Montepulciano. You also enjoy plenty of free time to explore each village on your own.

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.

Sip Tuscan wine in a medieval castle during a tasting session in Montalcino. Hosted by a professional sommelier, the experience ensures you get the lowdown on the wine as you taste it. Enjoy three varietals including a glass of the prestigious Brunello di Montalcino DOCG, along with local bread or breadsticks and olive oil.

A mere 6 km from Siena, immersed in the poetic and permeating beauty of the Senese countryside the small San Giorgino church, has since 1109 placidly observed the vineyard and olive trees of the surrounding fields, which have been under the stewardship of our family since 1977, where with love, tradition, dedication and innovative spirit we have produced wine and oil. We love to define our company as a harmoniously multifaceted reality that holds a myriad of souls inside of it. By fine tuning each one of the contrasting elements together, like an orchestra, we give life to unique products that are recognizable, inviting, and sincere: symphonies of genuine tastes, rooted in the culture of the land. This reality begins with our family: we are in 8 and all contribute in the company with our own specializations, following the entire production process, from the preparation at the vineyard, to the last step of commercialization.

Leave the planning and driving to someone else on this daylong winery tour specializing in Brunello di Montalcino—a wine produced in the vineyards around the town of Montalcino. Visit historic wine cellars and vineyards, have lunch in a winery in the hill town of Montalcino itself, and visit a winery in the nearby Nobile di Montepulciano area for good measure.

Tuscany is known for its excellent vintages, but the world of Tuscan wine can be overwhelming for a novice. With this informal wine class, you’ll get your bearings and learn to recognize the most important and storied wines of Tuscany. Delve into the history of Tuscany’s wine production, discover the different wine-producing areas and grapes, and sample a number of reds and whites from the region.

Siena sits in the heart of Tuscany, known across the globe for its excellent regional cuisine. Delve into its traditional specialties with this foodie experience that combines a lesson covering Tuscan wines and gourmet delicacies plus a foodie stroll through the old town to sample them for yourself. Taste a variety of wines paired with cheeses and charcuterie, extra-virgin olive oil, bread, jams, and honey.

Combine two of Montepulciano’s highlights—spectacular landscapes and world-class wine—in a single experience with this Vespa tour through the countryside plus wine tasting at a local cellar. Zip through the Val d’Orcia or around Lake Trasimeno on an iconic Vespa scooter (drive yourself or opt to ride with a driver), stopping to snap photos and admire the view. Then end with a wine-tasting lunch at a winery in the Montepulciano hills.

The owner will take you on a walk through the vineyards and olive groves of the Estate, we will visit the church of San Giorgino from 1100 to then go to the cellars and find out how our wine is born and ages (vinification and aging cellar in barrels and aging in bottle). At the end of the walk, tasting of wines and typical Tuscan products with one of the owners of San Giorgio a Lapi.

Discover the fine wines and rich historical heritage of Chianti on a full-day trip from Siena. With a knowledgeable guide, travel through the sublime Tuscan countryside and visit castles cradled by rolling green hills and sprawling vineyards. Visit Castello di Brolio, the esteemed birthplace of Chianti wine, and delve into the opulent chambers of Castello di Ama. Pleasure your palate with fine samples of Chianti Classico wine during tasting sessions and feast on a traditional Italian lunch during your tour. Enjoy an intimate atmosphere on this small-group tour, limited to only eight people.

Many of Italy’s most charming hill towns are a challenge to reach with public transport. With this day trip, round-trip transport takes the stress out of visiting Volterra and San Gimignano and gives you time to explore both in a single day. Enjoy seamless pickup and free time in both towns, breaking up your visits with lunch at a Chianti cellar accompanied by a tasting of five different wines.

Winery Tour and Wine Tasting in Siena with Afternoon Meal. Immersed in the magical atmosphere of rural Tuscany, just a stone's throw from the old town of medieval Siena, the experience is a journey into the history, culture, tradition, and science that give life to every bottle of our organic wine. During the winery tour we will analyze together the characteristics of the vineyard agro-ecosystem and the techniques used to preserve and regenerate rural resources. In our old wine cellar, we will take you through the fascinating world of winemaking and the secrets behind crafting quality wine. The tour will end in our tasting room, where you will grasp all the organoleptic nuances of our young and vintage wines. Each glass will be paired with the best seasonal Tuscan products, to delight your palate and nourish your soul.

Nestled in the Chianti hills, visit the estate, whose villa is the historical testimony of a history dating back to the year 1000, and taste high quality Chianti wines with a classic soul in this “Controlled and Guaranteed Designation of Origin” path, which begins in the vineyard and then takes you to discover the cellars

Inject a bit of adventure into your wine tasting experience with this ATV tour through the vineyard-covered countryside surrounding Siena. Take in views of the UNESCO-listed Crete Senesi landscape as you zip over the hills behind your guide, following unpaved trails through woods and fields. End at a family-run cellar to sample Tuscan wines paired with local gourmet specialties.

Spend a day riding along peaceful roads through the scenic, Tuscan hills on an original Piaggio Ape Calessino. Experience a unique way of admiring Chianti's sights, and stop for a wine tasting and delicious lunch along the way.

Paradiso di Cacuci is a winery located in a small “corner of Paradise“ in the northwestern area of ​​Montalcino. Our wine production is centered on the perpetuation of the tradition which, together with a more modern model and in compliance with the values ​​of the Brunello Consortium, uses only from our vineyards which are respectively divided into; 5 ha Brunello di Montalcino, 1 ha. Rosso di Montalcino and 5 ha. di I.g.t. Sangiovese. Welcomes, by reservation, individual visitors and small groups offering guided tastings that give the opportunity to get to know the production directly, starting from the winemaking process to the discovery of the final result, giving a unique and unforgettable experience. Our tastings are only private and by appointment only to guarantee you our best services.