2019 Walkshop through Tuscany

Get your ideas - and yourself - out in the open

The 2019 Walkshop will take us through the Italian countryside as we explore the rolling hills, vineyards, and medieval towns of Tuscany on a multi-day hike with other technology and design thought leaders.

A select group of 15 people will recharge while being offline - walking and wandering in small groups through the picturesque backdrop of the Italian countryside. These 15 will discuss a question and then swap topics when a line of thought has run its course. The path we follow through Tuscany will help guide interactions: the path will narrow to restrict a discussion to a single pair of walkers who can fit together on the trail. And later, as larger spaces open up, the path will allow for us to regroup, slow down, and take stock of our surroundings.

Ideas tend to flow more freely in a Walkshop than they would around a conference table. People are more inclined to ‘think outside the box’, and come up with fresh and radical insights and innovations when they go off the grid for a few days. And by the second day of the hike - the normal inhibitions and pretense all melt away while you focus on the trail, your destination, your companions, and yourself.

We hope you can attend this fall to gain new insights and build new connections.

Tickets Prices in USD

I can't go this year - but would like to stay informed about future Walkshops

Additional Information

Friday, Sept 13th: Fly to Florence, Italy
That's right - start your journey on Friday the 13th. Risk it!

Saturday, Sept 14th: Arrive in Italy
Land in Florence and take transportation to Montepulciano, in the Province of Siena. Unpack, stetch, and get over jetlag. Stay over night and get ready for the trail.

Sunday, Sept 15th: First Day on the Trail - 15km
A lovely walk through undulating and iconic landscapes, passing wineries, vineyards and olive groves galore and finishing in the splendid hill top town of Pienza.

We will make our way out of Montepulciano and through one of the town's old gates before heading out into the surrounding countryside. Upon reaching San Bagio Church, we will then be walking along gravel roads and past vineyards and olive groves, with Montepulciano getting smaller and smaller in the distance. From the trail as we walk onto a plateau there are really great views to look forward to, with Monticchiello and Pienza in the distance. We will have lunch in the lovely little village of Monticchielo and make one more brief descent before making our way uphill to the very pretty hill top town of Pienza.

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Monday, Sept 16th: Second Day on the Trail - 16km
A lovely walk beginning in Pienza and finishing in the spa village of Bagno Vignoni with consistently fantastic views.

This is a particularly great walk as most of the time we will be able to see where we've been and where we are aiming for. Today's hike contains iconic views across the valley with typical Tuscan scenery of cypress trees, rolling farmland and olive groves. We will venture into the outskirts of San Quirico d'Orcia - a walled city with an elegant 12th century church and gardens. We will conclude the hike in the village of Bagno Vignoni with its hot springs.

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Tuesday, Sept 17th: Rest Day and Unlearning Workshop
On Tuesday, we will take a break from the trail and take transportation to Montalcino. Once there, we will keep you on your toes (even when you're not on your feet) with a series of workshops on the theme of unlearning. As our access to knowledge becomes easier, it is also getting obsolete at a faster pace. It becomes apparent that in order to learn something new, we need to first get rid of (or, unlearn) something old; and the best way to make shifts is through interactive learning. In these workshops, we will use design thinking, visual thinking, and applied improvisation to uncover obstacles and unlearn conventional ways- of-thinking in order to make room for new breakthroughs.

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Wednesday, Sept 18th, Third Day on the Trail - 12km
We will transfer in the morning to the very impressive abbey of Sant' Antimo. From there, we climb to a ridge along dirt tracks which is dominated by views of the castle on the hill, Ripa d'Orcia. In the afternoon, we'll descend to cross a riverbed before heading into the medieval village of Castelnuovo dell'Abate. There are fine views down the valley with iconic Tuscan scenery and vineyards galore.

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Thursday, Sept 19th, Fourth Day on the Trail - 17km
A linear route from the hill top town of Montalcino to the Pieve a Salti Agriturismo with constant views of the Crete Senesi.

We will begin at the ancient gate of Porta Burelli in Montalcino and descend into the valley, walking past a few vineyards. On day four, we will pass many farms en route and perhaps run into some sheep being herded along the way! We will follow the Via Francigena for a little while before heading into a field and down a dirt track before ascending again to the final ridge. The final 3 km are flat as we walk to our agriturismo where, weather permitting, we can relax by the swimming pool.

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Friday, Sept 20th - Travel Day / OPTIONAL: Extend for a weekend in Siena
We will depart the Tuscany hillsides and take transportation to Siena, a UNESCO World Heritage Site. For those who are looking to return home, take transportation back to Florence. Optionally, stay an extra 2 nights in Siena and explore this ancient Italian city.

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What's included in my ticket purchase?

  • Stay in friendly, family-run guesthouses, inns, and hotels along the way

  • Relax in private bedrooms and accommodation

  • Big breakfasts will keep you going all day long

  • Luggage? Don't worry, we'll move it for you! All you have to do is focus on the hike - your gear will be waiting for you at the next B&B.

  • Detailed maps/notes mean you'll never get lost (And waterproof map-case keeps your maps dry)

  • Get insider tips on the best places to eat and drink along the way

  • Explore the local history of Italy and discover the most exciting attractions on the trail

Your RSVP covers the hotel costs at each stop along the trail and breakfast every morning. (Any trail snacks, lunch, dinner, and evening drinks will be on you). Airfare and transport to and from the trail will be your responsibility - but all transport once we arrive around the trail (including moving your luggage each day from stop to stop) will be provided for you.