Client:
Box of Crayons, a Toronto based learning and development company that partners with large, global organizations to deliver practical, interactive, and transformative learning experiences.
Objective:
Reward the team for hitting key targets with a relaxed, culturally rich retreat that felt like a true break, not another offsite packed with meetings.
The Story
Box of Crayons had reached an important milestone. The team had worked hard, hit their goals, and leadership wanted the celebration to reflect that effort. A simple gift or virtual party did not feel right for a company that spends its days helping others create meaningful learning experiences.
They envisioned something different. A long weekend away, shared in person, where people from Toronto, Vancouver, Calgary, and Edmonton could reconnect as colleagues and as people.
The leadership team made the following requests:
- A short trip that would not be dominated by travel
- A budget of roughly 3,000 dollars per person
- A destination that felt new and energizing but not overwhelming
- Activities that went beyond beaches and snorkels
- Only one light business touchpoint, so the focus stayed on rest and connection
What they did not have was the time or confidence to design a multi day international retreat on their own. With limited internal bandwidth and a lot of variables to juggle, they looked for a partner who could take the lead on planning, present clear options, and handle the details.
The Ask
Box of Crayons asked Pilot to:
- Propose 3 to 4 retreat options that fit their budget and timing
- One within Ontario
- One elsewhere in Canada
- Two to three international options in places like Colombia, Costa Rica, or Mexico
- One within Ontario
- Keep flight time reasonable from multiple Canadian departure cities
- Focus on cultural experiences and varied activities, not a beach resort
- Coordinate for 15 people traveling from different cities, on slightly different schedules
The goal was to give the team a meaningful, low stress reward trip where they could celebrate a strong year together.
The Solution: A Four Night Retreat In Guadalajara, Mexico
From the initial set of options, Guadalajara emerged as the clear front runner. It balanced everything Box of Crayons had asked for: mostly direct flights from Canada, strong value for money, rich culture, walkable neighborhoods, and a sense of familiarity without feeling touristy.
Planning began in early August for a late November trip. Over the following weeks Pilot:
- Secured a centrally located boutique hotel that could host the full group and provide comfortable shared spaces
- Organized airport transportation for staggered arrivals and departures
- Built a four day itinerary that blended guided experiences with open time
- Coordinated restaurant reservations, dietary considerations, and a private space for an informal team awards moment
- Designed a custom photo scavenger hunt in the nearby arts district of Tlaquepaque, turning exploration into a shared game
The pacing of the retreat followed a simple arc:
- Arrival and Welcome
- Smooth transfers from the airport
- Time to settle in, then an easygoing welcome dinner so everyone could reconnect face to face
- Smooth transfers from the airport
- Discovering Guadalajara
- A day shaped around the city itself, from historic plazas and museums to a guided walking tour with a local expert
- Dinner within walking distance of the hotel, which kept the day feeling relaxed and cohesive
- A day shaped around the city itself, from historic plazas and museums to a guided walking tour with a local expert
- A Day Trip To Tequila
- A full day excursion to the Tequila region, including distillery visits and shared time in the countryside
- An unscheduled evening, giving people the freedom to rest, explore in small groups, or enjoy the city at their own pace
- A full day excursion to the Tequila region, including distillery visits and shared time in the countryside
- Tlaquepaque, Scavenger Hunt, and Celebration
- A late morning departure to the colorful streets and galleries of Tlaquepaque
- Teams followed clues for a photo scavenger hunt that invited them to notice details, interact with public art, and document their own version of the neighborhood
- The retreat closed with a farewell dinner in a private dining area, where leadership could host lighthearted team awards and reflect on the year together
- A late morning departure to the colorful streets and galleries of Tlaquepaque
Throughout the trip, the group could reference the shared itinerary in the Pilot app whenever they needed meeting points, addresses, or timing. For the team, it simply felt like everything flowed.
The Results
For Box of Crayons, this retreat was a test of a simple idea. If you remove the planning burden and choose the right structure, a short reward trip can have an outsized effect on how a team feels heading into the next year.
By handing over the logistics, the leadership team recovered an estimated 115 hours that would have otherwise gone into research, comparison, booking, and coordination. Instead of troubleshooting flight seats or restaurant capacities, they were present with their people.
The outcomes were exactly what they had hoped for:
- A well organized, detailed retreat where the team could relax and enjoy themselves
- Time together that felt celebratory, not scripted
- Stronger personal connections across offices and roles
- A sense that the effort of the year had been seen and appreciated in a tangible way
Everyone who attended came home with shared stories, new memories, and the feeling that the trip had been worth far more than the logistics that made it possible. This was not a strategy summit or an offsite packed with sessions. It was a reward, designed with care, that reminded a distributed team what it feels like to be on the same page in the same place.