A remote tech company approached us with the challenge of creating a week-long corporate retreat that would not only bring their employees together for a memorable experience but also deeply immerse them into the local surroundings. 

We set to work researching destinations and developing an agenda that would incorporate a balance between strategy meetings, work sessions and a slew of mind-blowing corporate team building activities. We finally settled on Italy, more specifically Tuscany with its much loved cuisine, alluring architecture, landscapes, and deep history made it the ideal destination to host the retreat. With the picturesque Tuscan countryside as a backdrop, the inspiration to create an epic Italian Job inspired by the Amazing Race became the core challenge. 

Take a look at the wrap-up video we produced at the end of the week before diving into the details:

The Theme

Trails of Tuscany, pitting competing contradas (teams), historical neighborhoods in Sienna, against each other in a series of team-building activities throughout the week. Teams were awarded points based on their performance in each activity and the tally was monitored throughout the week. The victories team was announced at the gala dinner on the final evening.     


At a glance, the agenda looks jam-packed! But we can assure you that there was plenty of time for the group to gather, hang out and get to know each other. While they may work together on a daily basis, they are often sit on the other side of the world or multiple time zones away. So downtime between the epic challenges was factored in and prioritized for more intimate interactions, impromptu video game tournaments and games of Bocce Ball. 

Day 1 | Welcome Reception at a 13th Century Castle

Calling a 13th-century Tuscan castle home for the week, the group was welcomed with a hearty antipasto Cena in the fragrant courtyard among the lavender bushes whilst being serenaded by a musical trio with the sunset performing the backdrop to the opening evening. 

Dinner on the first night took place on the lawn of the 14th c. castle with an incredible view of the Tuscan country-side

Moniker's Top Hotel Pick: Castello di Gargonza

The little walled privately-owned Tuscan village of Gargonza, perched atop a hill overlooking Chiana Valley is comprised of 13 buildings, that have maintained their authentic structure and original atmosphere thanks to the careful restoration process. But the crown jewel of the little village is La Torre di Gargonza Restaurant serving traditional Tuscan dishes al fresco, for the perfect Italian experience.

Original finishings, terracotta floors and wood-beam ceilings adorn the 45 rooms scattered around the village, making this the perfect property for an intimate corporate retreats.

Other Hotels to Consider: Toscana Resort Castelfalfi 

From the historical charm of its medieval heritage to the luxury of its modern accommodations, consider Toscana Resort Castelfalfi if you are looking for a more luxurious experience. This impressive 5-star manor holds a prime location in the heart of the Tuscan hills. Boasting an array of amenities including spacious conference facilities, multiple restaurants, a golf course, pool, and spa.

The hotel's 120 guestrooms sit in contrast to the more traditional building in which they are set, designed to be sleek and stylish - offering more upscale accommodation than most hotels in the area. 

The sprawling Toscana Resort Castelfalfi hotel in Tuscany

Day 2 | Meetings & The Italian Amazing Race

Kicking the retreat off with a morning of productive meetings it was time to venture out. The group was told to meet at the entrance and wait for the bus - for an afternoon of sightseeing. Only to be interrupted by a member of the Carabinieri screeching up the driveway to announce, “there has been a bank heist!”

The police officer introduced the challenge to the group and led them around the corner to where over a dozen Fiat 500’s were hiding. Dividing the group into smaller teams, each team was given two cars, a walkie-talkie and a docket of clues. 

The Carabinieri coming to tell the group about the bank heist!

Teams were responsible for dividing tasks among themselves and managing their time. As clues were spread out over a one hundred kilometre radius from the castle. 

Behind the scenes, the real challenge was creating riddles and leaving a trail of clues that would be engaging enough to create a real investigation whilst not obvious enough to simply Google but still being possible to solve in the given time limit. 

The first clue directed them to the nearby town of Monte San Savino, where they discovered an eye-witness (hired actor) that had his hands bound, and mouth taped. The eye-witness steered the teams to their second clue as he handed over a scrap of paper that fell out of one of the perpetrator’s pockets during the robbery.

The groups had to communicate with the 'locals' to solve the clues

After nearly 6 hours of weaving through the labyrinth that is Italian country roads, visiting three villages across Chianti Valley of Tuscany and interacting with a mix of paid actors and local shop owners - including a barbershop the thieves frequented, a hotel they had stayed at and a restaurant where they were overheard plotting their grand heist. Word was eventually put out that the police had rounded up a few suspects and the teams were needed back at the castle to help identify the true thief.  

The perpetrators were given the opportunity to mingle with the attendees (investigators) to share their alibi’s and in the end, each team was required to submit a list of their top three suspects. 

That evening over a home-cooked Italian dinner the winning team was revealed along with a tally of all the bonus points accumulated for solving the riddles and collecting photographic evidence of the journey. 

Teams had to chat with those in the police line-up to determine who the perpetrators were

Day 3 | Trials of Tuscany Team Activities

Proceeding an action-packed day racing around Tuscany, and teams still buzzing - the day launched with a morning of collaborative work session and flash talks. Followed by an afternoon of small team building activities - Trials of Tuscany - around the castle. Teams dashed around the castle grounds from station to station solving various word searches and compete in lawn games to complete The Trails of Tuscany. 

Another challenge to pit the contradas against one-another

Day 4 | Day in Florence

Straight after breakfast, the group was whisked off to the iconic city of Florence, for a morning of surprises and an afternoon of optional activities. On the banks of the Arno River, the group was introduced to the historic members-only Rowing Club, which we are privileged to have access to via some local friends and contacts. Here everyone was split to compete in heats of 2 boats, head-to-head in teams of 12-16 people. The Dragon Boat Regatta serves to flex teams endurance and communication skills as they race up and down the banks of Florence's most famous river and the iconic Ponte Vecchio serving as the finish line. 

Learning how to row as a team on land before heading to the boat
Teams raced up the river to and under the historic Ponte Vecchio

After working up an appetite, the group headed back to shore for a delicious lunch at the Rowing Club, before splitting off to their choice of optional activities. Everyone had the opportunity to either participate in a group food and wine tour, a historical walking tour or spend the afternoon at their leisure exploring the wonders of Florence 

The week culminated in a medieval-themed grand gala dinner in the castle courtyard under the stars. Marching the last evening to a crescendo with the recreation of Palio Del Niballo of Faenza, a spectacular time-honoured event that has flag-wavers move through a choreographic sequence to the beat of drums and trumpets, concluded the epic week. An Italian feast and the announcement of the winning contradas closed out the night.  

Day 5 | Final Departures

With a week of team-building challenges, a collection of shared memories and a few once in a lifetime experiences behind them it was time to say arrivederci. We love hearing from our participants in the post-survey feedback, and here was one of our favourite quotes after the trip since it really highlights why we think retreats are so important. It answers the question, what was your biggest take-away from the retreat? "What a privilege it is to work for this company - and that I love my colleagues. The Retreat was inspiring in so many ways - you can grow great bonds working in such close proximity for even just a few days."