Planning and offsite in 2026?
Here are 3 mistakes companies make and how to avoid them
At Retreat, we plan offsites for teams of all sizes across Europe, LATAM, USA and Asia. After organizing hundreds of events, we’ve seen the same challenges come up again and again.
Here are the top 3 mistakes companies make when planning an offsite… and how to avoid them.
🗓️ 1. Booking the venue too late
Most teams start sourcing hotels only 2-3 months before the event.
But for groups of 40+ people, especially in peak seasons, this is way too late.
What happens?
- Higher room rates
- Limited meeting room availability
- No flexibility on dates or setup
How to avoid it:
Start sourcing 5-8 months in advance and secure the hotel first. Everything else (activities, F&B, transport) depends on it.
✈️ 2. Choosing a destination with poor flight connectivity
This is one of the biggest hidden pitfalls in offsite planning and it can silently inflate your budget and your headaches.
Why it’s a problem:
- Longer travel times → tired participants
- More layovers → higher risk of delays & missed luggage
- Harder to coordinate group arrivals & transfers
How to avoid it:
Choose destinations with:
- Multiple airlines and regular flights
- Strong international airport hubs
💸 3. Booking more rooms than you need & lacking budget control
This is one of the most expensive mistakes companies make. Often without realizing it until the final invoice arrives.
Why it’s a problem:
- Overestimating attendee numbers leads to unused rooms = unnecessary costs
- Hotels may charge penalties if you reduce too late
How to avoid it:
- Finalize your attendee list early (and track real-time changes)
- Negotiate a favorable attrition clause with your hotel (we can help you with that!)
- Use a consolidated budget file