“The earlier, the better.” is what they say when it comes to company retreat planning timelines. But here’s the reality: you don’t have to do everything at once. Below, we’ll break down the myths and get real about the time you actually need.
“The earlier, the better.” is what they say when it comes to company retreat planning timelines. But here’s the reality: you don’t have to do everything at once. Below, we’ll break down the myths and get real about the time you actually need.
We get it—you’ve already got a full plate, and now you’re expected to add ‘company retreat planning’ to your long list of tasks.
Venue? Flights? Restaurant bookings? Passports? Meeting rooms, merch, coffee breaks, airport transfers…It feels like it never ends.
If you’re breaking a sweat just thinking about it, trust me, we’ve been there too. It can feel overwhelming, like you need to handle everything right now to keep it all from falling apart. And then there’s the infamous line: “The earlier, the better.” As if that’s going to calm your nerves.
But here’s the reality: you don’t have to do everything at once. Not all timelines are as urgent as they seem.
What timelines really need your attention, and where can you hit pause for a bit? Let’s break down the myths and get realistic about company retreat planning timelines.
Let’s kick off with the one deadline you really don’t want to miss: the venue. Here, the “earlier, the better” rule actually holds true.
Getting the venue sorted well in advance is crucial. Customers often come to us looking for a venue with just three months’ notice. We find something, sure, but it’s rarely the dream spot. You might end up compromising, like having to rent a meeting room elsewhere because the venue’s one is already booked.
Why book early?
The benefits?
You save money, get a nicer venue, and avoid the hassle.
Bottom line: don’t miss the 12+ month deadline in your company retreat planning process.
Great. The venue is booked. You can breathe.
This one’s a little more relaxed. We’re talking boat rides, cooking classes, biking tours, or team-building games. Activities are important, but you don’t have to stress as much about booking them super early.
Why?
However, for activities involving larger groups (50+), it’s a good idea to plan at least 6 months in advance. Coordinating activities for that many people takes a bit more time and effort.
Ever waited too long to book a holiday flight and ended up paying way more than you planned? The same thing can happen with retreat transportation if you wait too long. That’s why sticking to the 4-6 month window is key in retreat planning—especially if you want to stay on budget.
Flight bookings? Book them early. We’ve even got tips on the best ways to handle flights for company retreats [link here].
When it comes to transfers (airport and activity transport), don’t delay either. We’ve had our fair share of nightmares with providers. That’s why we only work with a few trusted ones now. You’d be surprised how often drivers don’t even know where they’re supposed to go!
The takeaway: Secure your transfers early. You won’t necessarily save money, but you’ll save yourself a ton of stress by locking in quality.
Now’s the time to take a breather. We completely agree that meals are a big deal. They provide energy for working, bring people together socially, and give everyone a taste of the local culture. But luckily, the planning process is pretty laid-back.
Hotels don’t need final meal plans too far in advance. Most will ask for dietary restrictions 1 month to 2 weeks before the retreat, and menus are usually confirmed around the same time. Want to add a coffee break or a cocktail hour? Hotels tend to be flexible—even if it’s last-minute.
Restaurants are a bit trickier. For groups over 10, it’s best to book 2 months ahead. This also gives you time to gather everyone’s meal preferences. And if things don’t go to plan (because sometimes they don’t), we’ve even managed to arrange tables for 25 the day before—so nothing is impossible.
Pro retreat planning tip: When you first book, let the hotel know the minimum number of meals you’ll need and for sure will have, and you can always add more closer to the retreat. It’s way easier to increase meals than to deal with payments or refunds later on.
Voilà. It’s one week before the retreat, and you’re nearly there. The last few days are all about reminding participants what to pack, going over everything one more time, and making sure all providers are good to go.
Most websites will tell you to start your company retreat planning as early as humanly possible. But in reality, that can bring more stress than it’s worth. Every project runs smoother with structure, and retreat planning is no different.
Here’s the truth: after 9 years of experience, we’ve learned that the mainstream advice to plan everything “as early as possible” isn’t always helpful. Yes, booking early gives you flexibility, but often the stress of rushing isn’t worth it. Stick to realistic deadlines, and your retreat will come together just fine—without the panic.
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