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Discover Montalcino, the hillside southern Tuscan town known for its lavish full-bodied wine, Brunello di Montalcino. From Siena, travel via comfortable minivan or coach on this guided tour of Montalcino. Once in town, learn about the town’s medieval past, see gothic churches and rustic buildings and then take some free time to explore on your own, perhaps shop for a bottle of Brunello or two. Visit the Romanesque church, Abbazia di Sant’Antimo, and then tour the vineyard, trying a variety of Tuscan wines. 


  • Half-day trip to Montalcino and Abbazia di Sant’Antimo from Siena
  • Travel through the UNESCO-listed Val d’Orcia region to the hill town of Montalcino
  • Enjoy free time in Montalcino to soak up the views and visit the wine shops, if you wish
  • Visit Abbazia di Sant’Antimo, a Romanesque abbey with stunning Travertine sculptures
  • Sample wines on a Tuscan winery tour and try the world-renowned Brunello di Montalcino

What You Can Expect

Montalcino and Abbazia di Sant’Antimo Day Trip from Siena including Wine-Tasting

Take a stroll around Monlalcino and admire the views!

Meet your guide and then head out of Siena, going south to Montalcino, a hilltop town of medieval churches and cobblestoned streets that is famed for the wine it produces: the lauded Brunello di Montalcino and its more affordable sibling Rosso di Montalcino. 

On the way there, learn about the history of the town from your guide, as well as, about the wine production around the town. Hear what makes Brunello one of the world’s best varietals. Upon arriving in town, spend some time on your own, strolling the streets and popping into one of the many enoteche, the wine shops that double as bars, where you can drink wine right there on the spot or purchase a bottle or two to drink later. Or stroll up to the 14th-century fortezza, the imposing castle at the top of the city, where you can get a stunning view of the the classic Tuscan countryside: the rolling hills, the villa-crowned hills, the vineyards. 

At a pre-arranged time, meet up with your guide again and go to nearby Abbazia di Sant’Antimo, an incredible Romanesque church made with Travertine stone that is set in a tranquil valley. The abbey is a typical stop for pilgrims who are walking the Via Francigena, a long medieval pilgrimage route that stretches from Canterbury in England all the way down to Rome. 

Inside the the abbey, gawk at the early Renaissance-era frescos and the sunlight that shines in from the windows. If luck is on your side, the may be a live Gregorian chant happening by the monks who live in the abbey. 

After lingering around the abbey for a while, board the bus and head to a nearby winery to conclude the trip on a ruby red-colored note: sample some of the local wines including Brunello di Montalcino and a few other locally produced wines. 

Go back to Siena in the early evening having just had a satisfying day exploring southern Tuscany.

Customer Reviews

Amber F

5 star rating: Highly Recommended October 2016

It was my first time in tuscany and also wine tasting. Of course Tuscany blew me away and the wine tasting trip was also an amazing experience but the guide and driver made it one of my best first experiences ever. The winery we visited had some real good wines and I have ordered 6 bottles to get shipped to my place. Overall one of the best parts of my trip to Italy


5 star rating: Highly Recommended June 2016

This tour was amazing!

Vivienne M

5 star rating: Highly Recommended June 2014

Such a fantastic afternoon!! Our guide, Marianna was wonderful - and Brunello Wine Tasting was just fantastic! Beautiful setting; a lovely hospitable and fun host in Paulo, whose English was wonderful; and with a setting to die for........The abbey at Sant'Antimo was just beautiful in fabulous surroundings; and Montalcino picture postcard! The only negative for me would be that half an hour isn't really enough time to visit Montalcino........but all in all a hugely enjoyable afternoon; where we met some wonderful people, who will surely remain friends!! x

Elizabeth W

5 star rating: Highly Recommended December 2013

The tour started in Sienna, which gave us the chance to explore the city, which was absolutely wonderful. Our guide picked us up. He was a wonderful man, who knew a lot about the region and shared lots of stories about Sienna and Florence history. We stopped along the way and had lots of photo opportunities. After some driving we got to Abbadia Ardegna, the winery where we walked around the factory and some vineyards. The absolute highlight was the owner of the winery, Mr. Mario. A vivacious and passionate about wine, 80 something year old man who has been working there for the majority of his life. He only speaks Italian, but whether you understand the language or not, you can still understand his passion for his winery and his Brunello de Montalcino wines! Otherwise the guide translates everything perfectly well into English. We tried several wines, which were delicious! After the wine tasting we drove on to Sant'Antimo which is a beautiful abbey. The architecture is sobre and gives space to reflect. On the ride back to Sienna all of us fell asleep in the car. I guess the wine tasting did it's work properly!

Thanks for a very wonderful and unforgettable day! The price and quality are a definite 5 star for us!


5 star rating: Highly Recommended December 2013

Great trip

Bradley B

4 star rating: Recommended April 2016

Myself and Girlfriend had a great time on this trip. There was great difficulty listening to the driver with the sound of the road and AC system. Saw amazing sites and the wine tasting was great although the place was under extensive construction, soon to be completed

James R

4 star rating: Recommended December 2015

When we left Siena is was a rainy cloudy day, but when we got to the mountains around Montalcino, there wasn't a cloud in the sky. The scenery was breathtaking. The town was quaint but with steep hills that would challenge anyone. Unfortunately, very few shops were open when we got to the town and the only food to eat was gelato. The abby was awesome too. We could hear the monks chanting while in there which was very nice. The wine tasting visit was better than your traditional sales pitch to buy wine. The guide there I think his name was Tony spoke no English the tour guide translated and was 80 years old. He flirted with all the women. The samples of wine and food passed out were very generous and the atmosphere there was fun. We were all a little tipsy on the bus ride home. It was a beautiful day. When we got back to Sienna, it was still raining.

Simon W

4 star rating: Recommended October 2015

Good tour, especially the visit to Abbazia di Sant'Antimo.


4 star rating: Recommended October 2015

A nice trip, to two scenic spots. Most of the trip time was taken up with the wine-tasting: five wines and then grappa to wash it down. Unguided time of an hour in Montalcino more time would have been appreciated, and 45 minutes at the abbey Abbazia di Sant'Antimo, where 20 minutes was more than enough. But still, a nice inexpensive excursion to 3 interesting places in an afternoon 2-8 pm .

Cathy S

4 star rating: Recommended May 2015

Good tour overall.

Abbey was interesting but would be better if we had been there for the chants- they could sequence the tour to ensure that.
cons- No guided tour of Montalcino- bus dropped us off for an hour on our own

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