No shoes required

How to host a destination offsite for your team or company

Trade the office for white sand beaches to boost engagement
How to host a destination offsite for your team or company
Photo: Gerisima (Shutterstock)
We may earn a commission from links on this page.

For most of us, a work-from-anywhere workplace model was a novel concept three years ago. While some businesses, like our team at VSC, offered weekly remote work days, the prospect of never returning to the office would have seemed unimaginable. For years, our offices were the center of our jobs, where we met with clients, collaborated with colleagues, celebrated wins, and solved problems.

Yet, when the pandemic forced us to abandon these familiar spaces, we found new ways to connect.

Remote work has opened up endless possibilities for employees throughout the global workforce. Working parents found new opportunities for flexibility and work-life balance, while others sought out travel and found happiness in exploring new cities or visiting friends and family while still getting their work done.

For many of us, however, something was still missing: in-person connection.

How to host a destination offsite

Offsites, retreats, and in-person get-togethers have taken rise to fill the void. These gatherings are an increasingly significant tool in building your culture at a work-from-anywhere company and reminding employees that their colleagues are more than just a face on a screen.

At VSC, our Partners hosted our team for our second 3-day retreat in Hawaii this past December. Stacked with team-building and fun group activities, we provided our team with opportunities to play, connect and celebrate collective wins.

Now, as we settle into the new year and establish plans for 2023, here are three ways to build an exciting and impactful offsite for your team:

A case for no work, all play

The pandemic proved that work could be done from anywhere. Spending time with your colleagues, however, cannot.

For teams like ours that have employees across 15 different states and two countries, we know that it isn’t always easy to get everyone in one place. When we do, we want to make the most of our time together in person.

In our experience, an all-play, no-work offsite works best. Instead of meetings or sitting in conference rooms listening to presentations, investing in small group bonding activities specific to your offsite location, like zipline, surfing, hiking, or horseback riding, can make a big impact in establishing a positive workplace culture. Each of these activities offers opportunities for bonding and enables teams to create lasting relationships and memories with their co-workers.

The reality is that people work together better when they understand each other. Your offsite should prioritize enhancing the collective EQ of your team by having fun and enjoying some much-deserved time celebrating while unplugged.

Provide flexibility in booking travel

Making it easier for your team to get together is an essential first step in pulling off a successful offsite. Provide your employees with a flight stipend based on what tickets cost and enable employees to make their own travel reservations. This way, they can choose their trip stopovers and how long they stay. As an added benefit of having a remote workforce, some of your team may choose to stay at the offsite location after it’s over.

Getting everyone to the right place at the right is the hard part, but that doesn’t mean you should skimp on the small things. Your offsite is an opportunity to prove the value of your culture—make it memorable with goodie bags featuring location-specific items like sunscreen, branded towels, water bottles, flip-flops, and branded gift cards for incidentals.

To ensure your team can revisit their memories once the trip is over, consider hiring a photographer available to take group photos and candid shots. Not only can these be used for social media after, but they will be reminders of the fun you had together.

Encourage employees to sustain connections

When colleagues form friendships, it can be hard to say goodbye at the end of the offsite. If your colleagues plan new times to meet up post-offsite independently, consider organizing local meetups once everyone returns home.

While having a dispersed workforce means that not everyone can make the local meetups every time, setting up a place, date, and time for small groups to meet in major cities can help them stick to their plans to connect IRL. After all, the offsite is just a couple of days a year. If your goal is to build a team that works well together all year round, especially as new members join, these smaller meetups will build on the momentum of the all-team gathering to solidify your company culture.

To get the ball rolling, share some of the upcoming meetup dates while you’re at the offsite.

Prioritize connection

As budgets shrink and the workforce with it, the value of connection is perhaps more critical than ever. By prioritizing your team’s enjoyment and ensuring they have opportunities to foster lasting relationships with their colleagues, your offsite will prove that your team can have the best of both worlds: a flexible work environment and the benefits of in-person connectivity.

Anne Sophie Hurst is a highly experienced agency professional with 20+ years of leadership in digital brand engagement for retail, tech, and start-up industries. As Head of People and Partner at VSC, she oversees the team and operations while cultivating a strong company culture distributed across fifteen states, two countries and five time zones where the firm’s 40 employees work remotely.