September 13 - 20, 2019 // Trail Difficulty: easy to mOderate

Medieval villages, historical towns, castles and defense systems, country churches and beautiful abbeys are scattered all over the territory and the rolling yellow hills of Tuscany. This region of Italy is home to swatches of olive groves, wine soaked villages, scenic vistas, incredible food, and historic sites - including Siena, a UNESCO World Heritage city. We will step back in time as we step through this region of Italy and explore its wine, wilderness, and walking trails.

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Unlearning Retreat

September 13 - 20, 2019

What to expect in Tuscany

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.


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. 

First Day on the Trail - 15km


Sunday, Sept 15th

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. 

Second Day on the Trail - 16km


Monday, Sept 16th

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. 

Unlearing Workshop

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. 

Third Day on the Trail - 12km

Wednesday, Sept 18th

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. 

Fourth Day on the Trail - 17km


Thursday, Sept 19th

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. 

Friday, Sept 20th: You made it to 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.


Frequently Asked Questions

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.

What will we be eating along the way?

Every morning, you will get a complimentary breakfast before we hit the trail. Lunch will be ordered individually, based on preference. Each night, we will book dinner reservations for the group. Feel free to pack any snacks or drinks you’d like for the trail.

What should I pack for the trip?

  • Passport

  • Extra cash (Euros) - most places will not take Credit Card

  • Backpack that can get wet and survive

  • Phone charger and converter

  • Journal

  • Good pens

  • Snacks

  • Lots of extra socks

  • Good hiking shoes (plus an extra pair of shoes)

  • Swim suit (optional) for hotel pools, sauna, hot tub

  • Rain gear and extra clothing. Dressing in layers allows you to adjust to changing weather and activity levels. Two rules: avoid cotton (it keeps moisture close to your skin) and always carry a hat

  • Spare plastic bags (keep things dry)

  • Sunscreen and sunglasses

  • Bug spray

  • Compass

  • Headset

  • Band-Aids (in case you get blisters)

  • First aid kit

  • Flashlight

  • Whistle

  • Knife or multi-purpose tool.

What homework / prep work is there for this trip?

For the Italy trip, we will discuss this book during our hike, as part of the theme on Unlearning.

“Part of the fun of Grant’s book is that he redeems behaviors we typically regard with puritan disdain. . . . Thought-provoking.”
—The New York Times Book Review
“Fresh research, counter-intuitive insights, lively writing, practical calls to action . . . Grant has a deserved reputation as an original thinker.”
The Financial Times
“Grant’s latest looks set to join the required reading lists of many companies across America.”
“[Grant] examines what successful non-conformists . . . have in common, all in an effort to help the rest of us learn how to do things like bust myths, speak truth to power, and avoid groupthink without getting sidelined.”
—The Washington Post
“Adam Grant is a serious social scientist, master storyteller and infectious optimist. . . . Originals is filled with fresh insights on a broad array of topics that are important to our personal and professional lives. Mr. Grant has an uncanny ability to infuse a familiar topic with deeper meaning and leave the reader feeling hopeful and a little exhilarated.”
—The New York Times DealBook

What will the weather be like?

Typically in September, Tuscany has highs in the 70s (F) and lows in the 50s (F)

How should I train / prepare for the hike?

The hike in Tuscany is easy to moderate - but still a good distance each day. Everyone should start a stretching routine before going on the trip and start increasing the amount of physical activity they experience in a typical day in anticipation for the trip. To help build an endurance, consider switching to a standing desk, purposefully start walking more on the weekends, or take your next 1:1 on foot and walk around the block as you talk with your peers!

For active alumni only