How to Plan a Company Retreat Without Losing Your Mind
(A step-by-step guide to doing it well - without the overwhelm)
The idea sounds great. The reality? Not always.
A company retreat is supposed to be inspiring - a chance to reconnect, reset, and build something deeper than day-to-day work.
But somewhere between “let’s plan an offsite” and “everyone’s arriving on Monday,” something shifts.
Suddenly you’re juggling venue quotes, dietary needs, dodgy wifi concerns, and trying to make the schedule feel more inspiring than a souped-up team meeting.
If you’ve ever been tasked with organising a retreat, you already know:
It’s a full-time job dressed up as a nice idea.
The 7 Most Common Retreat Planning Pitfalls
Before we dive into the how, here’s what trips most teams up:
Too Many Cooks
Everyone has ideas. No one wants to own the logistics. Cue chaos.
No Clear Purpose
“Let’s just get everyone together” sounds good - until you realise you’ve got no through-line.
Venue Overwhelm
The internet is full of “great spaces.” Half aren’t available. The other half feel like conference rooms with better furniture.
Trying to Please Everyone
The introverts want space. The extroverts want games. The execs want strategy. You want a nap.
Overpacked Agendas
You squeeze in workshops, dinner, yoga, team building, and a hike - and forget to leave time for actual connection.
Last-Minute Surprises
No AV. No parking. The room with a view is now the room with the bins.
No One Takes the Lead Onsite
You’re hosting and herding cats - instead of actually participating.
How to Plan a Company Retreat (Without Losing Your Mind)
Let’s make it simple. Here’s the roadmap we follow at Elsewhere - and it works.
1.
Define the Purpose
Before you talk dates or destinations, get crystal clear:
What is this offsite for?
Strategy reset?
Culture lift?
Cross-team bonding?
Creative ideation?
Celebration?
One sentence of clarity now saves 100 headaches later.
2.
Right-Size the Group
Think about what format suits the purpose.
Full company = 50–150 people?
Leadership team = 8–20 people?
Cross-functional sprint = 12–30?
Size determines everything from venue layout to tone.
3.
Choose the Right Format
Don’t default to the two-day, one-night model. Pick a structure that serves the energy:
1-day reset: Fast, focused, powerful
Overnight offsite: Combines space, depth, and bonding
Multi-day retreat: Total immersion, perfect for big shifts or annual planning
4.
Pick the Right Venue (Not Just an Available One)
A venue isn’t just a backdrop - it shapes the energy.
You want a space that feels human, relaxed, and built for focus and fun. Not a corporate shell.
At Elsewhere, we only work with venues we know personally - including our flagship, Hill House - so the vibe is right from the moment you arrive.
5.
Design the Arc, Not Just the Schedule
A great retreat has a rhythm. It moves like a story:
Arrival → Connection → Shared Purpose → Flow → Reflection → Return
Plan moments to breathe, bond, and shift gears — not just activities.
6.
Include Space for Nothing
It sounds counterintuitive, but downtime is rocket fuel.
The best conversations happen walking back from lunch.
The magic insights often land when no one’s speaking.
No one bonds over packed slides.
Leave space. It’s where the energy lands.
7.
Get Professional Help (Really)
You can do this alone. But you don’t have to.
We’ve seen the toll it takes when someone in ops or HR is handed the entire retreat - on top of their actual job.
That’s why we do it differently. At Elsewhere, we operate full-service retreats - from venue to vibe to the team building in between.
You don’t just book a space. You bring in a partner who knows how to:
Hold the energy of the group
Read the room
Adjust in real-time
Make the experience feel easy and inspired
So - how do you want your next retreat to feel?
Smooth? Strategic? Actually fun?
If you’re planning a retreat for later this year, now’s the moment to get ahead of the curve.
We’ll help you find the perfect Elsewhere venue, build a rhythm that works, and shape an experience your team will still be talking about next quarter.
Get in touch to start planning - or explore our venues to find your perfect starting point.