Crooked Monkey Retreat 2026: Why We Keep Coming Back

Every year, our team trades Google Meet for real-life conversations, shared meals, questionable travel-day coffee, and a week of creating memories together. As a remote-first company with teammates spread across different countries and time zones, our annual retreat has become one of the most important parts of our company culture. Not because we stop working for a week. Quite the opposite. The retreat gives us the chance to keep doing what we do every day—serving clients, managing projects, solving problems, and creating great swag—while spending time together in person. The work stays the same. The environment changes. This year’s retreat started the way all great retreats do: with airports, delayed flights, luggage, and a lot of excitement. Team members arrived from different parts of the world and, within minutes of reaching the hotel, the hugs, laughter, and inside jokes were already flowing. That’s always our favorite part. We spend months working together through screens, yet somehow the transition from remote teammates to in-person friends happens almost instantly. Once everyone arrived, we settled into a rhythm that felt very familiar. We worked together throughout the week, surrounded by laptops, coffee cups, and an endless supply of mate. Our shared Spotify playlist quickly became a character of its own. While all of this was happening, client projects kept moving forward exactly as they should. Orders continued shipping. Questions got answered. Designs got approved. New opportunities came in. We know we’re doing something right when the thank-you messages and positive feedback continue rolling in without missing a beat. Of course, retreat week isn’t just about coworking. It’s also where some of our best ideas begin.  

Monkey Talks

Our Monkey Talks returned this year and once again became one of the highlights of the week. These sessions create space for team members to share experiences, lessons, ideas, and perspectives with the rest of the group. Sometimes a Monkey Talk sparks a new initiative. Sometimes it changes the way we think about a problem. Sometimes it simply reminds us how much talent exists across our team. Either way, everyone walks away with something valuable.  

Snack Wars

Another tradition that made a return appearance was Snack Wars. Every year, teammates bring snacks from their home countries and invite everyone else to taste them. On paper, it sounds simple. In reality, it becomes a surprisingly passionate cultural exchange. This year we sampled treats from the United States, Israel, Venezuela, Colombia, and Brazil, while also welcoming Chile as the newest addition to our growing Snack Wars map. Some snacks earned instant fans. Others started debates. All of them gave us another reason to gather around a table and learn something new about each other.  

Monkey Talkie

Speaking of traditions, we also created a new one this year. We introduced an activity that involved heading out in small groups for walks focused on deeper conversations and sharing perspectives. The concept was simple, but the impact was significant. Without laptops, meeting agendas, or notifications competing for attention, people opened up about challenges, goals, ideas, and experiences that might never surface during a typical workday. The activity became such a hit that we’re already planning to bring it back next year.  

Retreat Swag

As a swag company, we’d be remiss if we didn’t mention one particularly important moment from the week: retreat swag day. Receiving swag is always fun. Receiving swag surrounded by the people who helped create it is even better. We spend our days helping clients use branded merchandise and corporate gifts to build connections with employees, customers, and communities. Experiencing that same excitement ourselves serves as a great reminder of why thoughtful swag matters in the first place. Great products create shared experiences. Shared experiences create lasting memories.  

Special Dinner

Thursday evening brought another memorable moment when the team gathered for a private dinner in a beautiful, intimate setting. The atmosphere felt warm, relaxed, and surprisingly familiar. Conversations flowed easily, stories got better with every retelling, and for a few hours we simply enjoyed being together. Those moments often become the stories people reference long after the retreat ends. And somehow, just as quickly as it begins, retreat week comes to an end. The final day always feels a little bittersweet. We start packing our bags, saying our goodbyes, and preparing to return to our normal routines. On Monday, we’ll be back on Google Meet. We’ll be working from different cities, countries, and time zones once again. But that’s the thing about retreats. The goal isn’t to replace remote work. The goal is to strengthen the relationships that make remote work successful. This year’s retreat gave us new ideas, new projects, new traditions, and more memories than we can count. It also gave us something even more valuable: a reminder that behind every order, every client conversation, every custom product, and every corporate gift we create is a team that genuinely enjoys working together. That’s what makes a great retreat. And that’s what makes a great company culture.    

Planning a company retreat, team offsite, or corporate event?

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