Summary

By September, two things are inevitable: someone in your office is already drinking pumpkin-spice lattes, and the words “We should’ve started sooner” are hovering over every COO, Chief of Staff, and unsuspecting Executive Assistant tasked with planning next year’s company retreat.

We know, because we’ve heard it hundreds of times at this point. That’s how many off-sites we’ve organised across Europe. And the number one regret? Waiting. 

Waiting until January, waiting until “after the holidays,” waiting until the panic sets in and the dream of a Tuscan vineyard buyout is reduced to a chain hotel off the motorway.

Why Fall is Prime Time

You can read our very well put-together article on the Proper Timing to Start Planning a Retreat. Or, we can cut to the chase and tell you… 

September is our unofficial start to 2026 company retreat planning.

Autumn is when companies get serious. Strategies are written, OKRs locked, budgets wrangled into place. 

Your offsite should be part of that planning cycle, not a logistical afterthought squeezed in when venue options have already shrunk to “conference centre with questionable carpets.”

Meanwhile, the organisations that started early are sipping wine in Provence, not scrambling for available meeting rooms near Heathrow.

Why The Cost of Waiting Costs More Than Just Money 

Think of retreat planning like air travel. Book in advance, and you get a window seat, decent pricing, and the satisfaction of choosing. Book late, and you’re in the middle seat at triple the cost, silently cursing your life choices.

For company offsites, the stakes are higher:

• The “dream” venue becomes “that will have to do”. 
• Budgets balloon because short notice always costs more.
  (Practical advice here: Retreat Without Regrets — Tips to Manage Your Retreat Budget.)
• And worst of all, the retreat loses its strategic edge. Instead of being a lever for clarity and alignment, it turns into another calendar obligation.
  (See how to tie your retreat to meaningful objectives: The Ultimate Guide to Work Retreat Objectives That Deliver Success.)

What Planning Early Unlocks 

When you start now - before the leaves finish falling - you unlock three things: choice, clarity, and calm.

Choice, because vineyard estates in Italy, eco-lodges in Portugal, and boutique Dolomite hideaways are still on the table. 

Clarity, because you actually have time to align your retreat with next year’s vision, not just the available dates. 

And calm, because come January, you’ll be ahead of the curve, not already behind it.

(For a full timeline and step-by-step planning guide, see How to Plan a Company Retreat (Fast): Timeline, Costs & Turnkey Options in Europe.)

Our Qwello Masterpiece: A Real Example of What Good Timing Achieves 

Let’s make our point clearer in the form of a masterpiece. The Holy Grail of corporate retreat planning: Qwello’s 2025 retreat

An entire vineyard estate in Italy, peak season, full buyout. Days were filled with paddle tournaments and cliff jumps, nights with vineyard dinners and karaoke under fairy lights.

Sounds dreamy, right? Here’s the truth: that kind of setup doesn’t fall into your lap—it’s booked solidly in advance. The only reason it happened is that Qwello started planning in September, when the best venues were still on the table. 

Because of that early timing, 99% of the team rated the retreat “excellent,” and the People & Culture team actually got to put their clipboards down and join in.

For their ops team, it wasn’t just a retreat; it was a career-defining win. The kind of success you don’t chalk up to luck, but to timing. Early timing.

Onsite Help at Your Offsite: Why OnsiteHub is The Boots-on-the-Ground Partner You Need

We’re not just spreadsheets and booking agents. We’re on-the-ground collaborators—local experts for local experiences. That means knowing which rustic estate will quietly bend the rules, which villa delivers more than the brochure promises, and how to make a retreat feel effortless for your team.

(More on why local experts make the difference: Why Are Local Experts the Way to Go When Planning a Company Retreat.)

Let’s go back to that big win with Qwello to show you what this really looks like. Yes, there were vineyard dinners and karaoke under fairy lights, but the magic was in the tough stuff too. Behind the scenes, we were juggling transport logistics, smoothing over last-minute hiccups, and even sneaking in surprise birthdays and themed décor. The best part? Watching Qwello’s People & Culture team finally put their clipboards down and actually join in.

(For insights into tackling retreat challenges, see The 5 Big Challenges of Retreat Planning and How to Smash Them.)

With more than 250 retreats and five years of doing this across Europe, we know the difference between good enough and unforgettable. And we make sure your leaders don’t just host the retreat, they get to live it.

Wrapping up

If the leaves are falling, it’s time to start. Your 2026 retreat isn’t just a line item—it’s a chance to reset, align, and build momentum.

Start early. Avoid the middle seat. And let’s make your 2026 offsite one you’ll still be bragging about in 2027.

(For more on how retreats drive team bonding and results, see The Psychology of Team Bonding: Proven Techniques That Deliver Lasting Team Success and 4 Insider Secrets for Successful Retreat Planning .)

🟢 Ready to start your 2026 offsite plan? Get in touch today.

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