From Montalcino to Sant’Antimo Hiking & Wine Tour

Walk through the intriguing beauty of the Montalcino countryside and its wild forests, rolling hills, Brunello vineyards, and olive groves


Full day


Private tours









Walk with us along the famous pilgrim paths starting from the old town of Montalcino to its charming Abbey in the countryside and from here to a Brunello winery to end the day with a glass in hand

A nice and easy hiking tour in the countryside of Montalcino seeing all the different landscapes that the Brunello terroir has to offer: the city walls, the dirt roads, the forest, the olive groves, the vineyards. On a 3-hour relaxing walk, far from the chaos and the crowd of tourism, we reach Sant’Antimo Abbey surrounded by the good vibes of nature.

We have lunch here under the shade of centuries-old trees with a gourmet basket lunch protected by silence and pure air. In the afternoon, we have the chance to visit this unique church with its botanical garden and gift shop featuring products made by monks. Finally, we walk a little further to a Brunello winery for the wine tour & tasting.


Your guide is an expert hiking guide with vast  knowledge about the area, its traditions, as well as its flora and fauna.

We start from the old town of Montalcino and slowly walk along the walls of the city where it is possible to take some of the best pictures towards Siena and the northern slope of the Brunello terroir.

Then we head into the silence of the forest. Here, it is possible to admire and recognize all the trees that are part of the “Macchia Mediterranea”, the typical forest of central Italy.

In about an hour and a half, we are on the rooftop of the Montalcino territory overlooking vineyards, farms, and olive groves. The view to the south is dominated by the imposing Amiata Mountain, a dormant volcano now mantled by untouched forests. To the east are the rolling hills of the Val d’Orcia that, depending on the season, look like the waves of a green or golden ocean moving in the wind. Instead, from the west  blows the gentle breeze from the Tyrrhenian Sea that carries with it the scents of the Tuscan coast.

Following the dirt roads, we start the descent towards Sant’Antimo Abbey that we reach in about another easy hour of walking. Here we can finally rest a little, drink the famous “holy” water (or “magic” water according to the Etruscans) that flows from the garden of the monastery.

For lunch, we have a gourmet basket waiting for us filled with homemade field-to-table delicacies prepared by Locanda Demetra that we enjoy under the shade of the centuries-old olive trees around the Abbey.

Later is time for a quick visit of the church and the botanical garden. From these plants, the monks used to produce medicine and cosmetics that can be purchased at the little gift shop inside the complex.

In the early afternoon, we start again on foot for a final easy walk of 30 minutes towards a nearby winery. Here we tour the property and taste 2-5 wines in the tasting room. If necessary, your guide will also provide a brief introduction to the correct way to taste wines as well as an explanation of how the Italian system of denominations works.

You will have the possibility to buy wine directly at the estates at the most reasonable price. We also provide the service to ship the bottles directly to your home. We will take care of your wine by storing it in a refrigerated depository until you are back at home to receive it.

At the end of our walking day, a transfer by car will take you back to the starting point around 5 pm.

What's included

  • Local, fluent English-speaking, food & wine expert guide who will accompany you on the tour explaining the secrets of the countryside
  • private tour and tasting at the winery
  • gourmet basket picnic lunch
  • transfer back by car to the starting point

What's not included

  • gratuities
  • transportation from/to your accommodation (available as an extra: contact us)

Length: 13 km (8 mi), about 3 hours walking

Elevation gain: 300 m+, 350 m- (900 ft+, 1.100 ft-)


Is this hike too hard for me?

This is an easy trek for anyone. We will stop as many times as you would like to talk about the area,its flora and fauna, to relax and to take pictures in the best spots. Be prepared to walk for 2-3 hours

Which kind of equipment should I bring with me?

Hiking boots or shoes (whichever is more comfortable), sunglasses, sunscreen, hat, a small backpack, a water bottle or a camel bag, a windbreaker just in case it gets windy

Are kids admitted on this tour?

Yes, we love kids in Italy, and they are always welcome. Be sure your children can walk for 2 or 3 hours or be prepared to carry them on your shoulders 🙂

Can you pick us up in Montalcino, Pienza, Montepulciano, Siena, Firenze, San Gimignano, Chianti, etc.?

Yes, of course. Before booking, we will provide you with a price quote for this extra service.

Departures: Everyday

Season: All year long

Start from € 100
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Would you like to modify this tour or design your own experience in Tuscany?
Let us know your needs and wishes and we will tailor the perfect program for your trip to Italy.

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Starting from € 100
From Montalcino to Sant’Antimo Hiking & Wine Tour