Brunello di Montalcino Hiking Ring

Walk and taste with us in an intriguing 250 square km of splendor featuring wild forests, rolling hills, Brunello vineyards, and olive groves


Full day


Private tours








Not Included

The eastern hillside of Montalcino hiking tour: discover on foot the secret of this magic land where grapes, passion, and tradition meet and blend together to create one of the most famous wines of the world

If you love wine territories with unique characteristics, the Brunello di Montalcino Ring Walk Tour is a great chance to experience the Terroir of Montalcino right from ground level.  Exploring the area on foot gives you a deeper look at and a more authentic feel of this territory.

We will meet people who work in the fields, lumberjacks, and hunters. We will make our way to farmhouses in the middle of the countryside where winemakers and olive growers work every day. We will taste wines from the barrels and grapes from the plants. We will be on out-of-the-ordinary tours and paths.

We organize this tour tailoring the itinerary to your fitness level and wishes, but usually it is a nice and easy walk that lasts from 2 up to 5 hours.

We start at around 9 am, but if it is too warm we will propose an earlier start to enjoy the cooler hours of the morning.

Your guide will be an expert hiking guide with a vast knowledge about the area, its traditions, its flora and fauna. From the old town of Montalcino, we will head towards the vineyards along a nice forest path.

After about a couple of hours, we will stop at the first wine estate to meet the owner and tour the property while sipping on a glass of wine. Here, you will taste 2-5 wines. If necessary, your guide will also briefly introduce you to the correct way to taste wines and explain how the Italian system of denominations works.

For lunch, we will either eat at the small restaurant by the farm or we will have a picnic lunch on the lawn depending on the season and availability.

In the afternoon, we will continue walking through olive groves, blooming fields, and vineyards to arrive at the second vineyard of the day in a completely different area with different views but they are always spectacular.

We will have a private tour during which you will meet the owner or one of the staff, a wine expert who will lead you through the property: vineyards, facilities, aging cellar. At the end of the tour, we will have our own area reserved for the tasting, usually with a view.

During the day, you will have the chance 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.

The final stretch back to the old town will be easy and relaxing to gloriously conclude this great walking ring in the Brunello Terroir with a return to the starting point at around 5 pm.

What's included

  • fluent English-speaking, food & wine local expert  who will accompany you throughout the day explaining the secrets of the countryside
  • tour and tasting at 2 wineries
  • light lunch at the estate OR picnic in the vineyard or olive grove
  • transfer back to the starting point by car if needed

What's not included

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


Is this hiking too hard for me?

This is an easy trek for everyone. We will stop as many times as you would like to explain the area, its flora and fauna, to relax, and to take pictures in the best spots. Be prepared to walk for 3-4 hours

What kind of equipment should I bring with me?

Trekking boots or shoes (whichever is more comfortable), sunglasses, sunscreen, hat, a small backpack, a water bottle or a camel bag, an windbreaker 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 kids 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.

Pickup Points: .

Departures: Everyday

Season: All year long

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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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Brunello di Montalcino Hiking Ring