If there’s one universal truth about planning a company retreat, it’s this:
The moment you ask, “Where should we go?” the chaos begins.
Employees suggest everywhere they personally want to visit, Slack fills with travel fantasies, and suddenly you’re trying to balance goals, budget, travel time, venue capacity, and 200 personal preferences at once.
After helping hundreds of companies choose their retreat location (and hearing candid feedback from retreat organizers), here’s what actually works.
Option 1: Ask the company where to go (“Any ideas?”)
→ Guaranteed chaos 🤯
This feels democratic… but leads to immediate headaches:
- Dozens of unrealistic ideas
- Destinations based on personal preferences, not company needs
- No alignment on goals, timing, travel complexity, or budget
- Expectations that you’ll never be able to satisfy
You end up with noise, not clarity.
It feels democratic, but:
It rarely reflects what’s best for the team as a whole — or for the budget.
Option 2: Do your research and present ONE option
→ The smartest, least stressful approach 🎯
This method feels less democratic… but it consistently delivers the best experience.
How it works:
- A Surf Office advisor gathers your goals, constraints, timing, and team distribution
- We analyze:
- flight paths
- travel time
- venue quality
- seasonality
- meeting requirements
- buyout potential
- We identify the best venues (usually 3–4 that truly fit)
- You pick one with leadership
- You announce the retreat
It’s structured, efficient, and avoids months of “What about this place?” ping-pong.
As Alina, Senior Operations Manager, put it:
“Working with Surf Office was a great experience. They understood what we wanted and provided several options that worked for us. The whole organization was smooth and supportive from the beginning.”
This approach works particularly well because:
- You protect everyone from decision fatigue
- You reduce political lobbying (“My mother-in-law lives in Singapore!”)
- You create confidence and clarity
Option 3: Present 2–3 options and let employees vote
→ Feels like a healthy compromise… but very risky 💣
This is the trap most first-time organizers fall into.
It seems reasonable: you filter options, and the team chooses.
But here’s what usually happens:
- You show 2–3 good options
- Employees immediately add 10 more
- Someone pushes for a totally unrelated idea (“We should go to Egypt!”)
- An executive casually supports one of these new ideas
- Suddenly… you’re back at zero
This method reopens the door to chaos and sets the expectation that the team is choosing the retreat... when in reality, they don’t have the constraints in mind.
The biggest reason this method fails? People focus on the destination instead of the venue.
And this is dangerous because a perfect venue in nice location beats an average venue in epic location. Every time.
This is a lesson experienced planners understand deeply.
Even Annika, Lead People Ops, highlighted how crucial expert-curated options are:
“Surf Office was always quick to respond and gave us different options that made it very easy to decide what’s best for our team. We don’t want to miss out on it again.”
So… what’s the chaos-free method?
The process used by seasoned retreat organizers:
- Let Surf Office identify the top 3–4 venues. Not destinations — venues.
- Choose ONE option with your leadership team. Close the decision loop early.
- Announce the retreat with confidence
No voting, no Narnia-level wishlists, no backtracking.
Why this works?
✔ Prevents political lobbying
✔ Avoids unrealistic expectations
✔ Saves weeks of wasted time
✔ Reduces stress for the internal organizer
✔ Protects the budget
✔ Ensures high-quality venues
✔ Guarantees travel feasibility
✔ Drives better retreat outcomes
Final takeaway
If you want a smooth, strategic, drama-free retreat planning process:
Don’t ask the entire company where to go.
Let experts shortlist the right venues.
Choose with leadership.
Announce it with confidence.
Your employees don’t want 20 options - they want a great retreat.
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