Plan Now for a Successful Summer Retreat
At transform.forward, we believe in the power of retreats. We host them for teams, and we make time for them as a team ourselves. Retreats provide a structured opportunity to step away from the daily grind, align on big-picture goals, and build stronger teams. We know that for many teams and organizations, summer can feel like a good time to host a retreat. But here’s what we also know: a successful retreat doesn’t just happen - it takes intentional planning, and that planning needs to start early!
We have started discussing our ideas for what a summer retreat might look like for the transform.forward team, so we want to share a few words of wisdom for leaders or managers who might be thinking about hosting a summer retreat for your team.
Why Plan Now?
Sure, summer feels far away when you’re still scraping frost off your windshield—but blink and it’s July. Team vacations, conferences, and the general “out of office” mood make scheduling tricky if you wait too long. By planning ahead, you increase the chances that everyone who needs to be there can attend, and you’ll have access to the best locations rather than scrambling for what’s left.
What Kind of Retreat Do You Need?
Before you book a cabin, conference room, or coastal Airbnb, take a step back and think: What does your team actually need right now?
The word “retreat” can mean different things, and defining the purpose is key to making the right decisions. Without a clear purpose, you risk creating something that feels more like an obligation than an opportunity. Here are a few types of retreats to consider:
Strategy Retreat – Focused, extended time to discuss long-term goals, set priorities, and map out a vision for the future.
Team Connection Retreat – A time for team bonding, often including activities designed to strengthen relationships and trust.
Restorative Retreat – A retreat designed to recharge and refresh your team, prioritizing wellness, reflection, and work-life balance.
Comprehensive Retreat – A mix of strategy, connection, and restoration, tailored to meet multiple needs.
You might assume your team needs a chance to unplug and recharge, but they may be feeling pressure to make important decisions and would prefer dedicated time for planning. Or maybe you’ve got a long strategic to-do list, but your team’s running on fumes and what they really need is rest and reconnection. Involve your team in the planning process so the retreat you design meets actual needs—not just the ones that look good on a whiteboard.
Key Considerations for Summer Retreats
Once you’ve got a purpose, you’ll need logistics. Some things to think about:
Scheduling: Summer is full of long weekends, vacation time, and “sorry I’m OOO” email replies. Aim for mid-week if you can and lock in the date early.
Location: Off-site can be great for a shift in energy. But the best spots book fast. Think about what kind of environment supports your goals—quiet, inspiring, collaborative—and find a venue that fits.
Facilitation: Even the best teams benefit from having someone guide the process. A neutral facilitator helps structure discussions, manage time, and create space for voices that don’t always speak first. It also allows you to be fully present and not worry about time or what you’ll be presenting next.
Agenda: Resist the urge to cram in every idea you’ve had since January. A jam-packed retreat agenda can leave people feeling more drained than energized. Build in buffer time, outdoor breaks, and space to think. This isn’t your chance to solve everything—it’s your chance to realign and reset.
Get Started Now
If a summer retreat is on your radar, don’t wait until sunscreen season to get serious. Start the planning process now, and you’ll thank yourself later (so will your team). And if you need inspiration, check out our previous blog posts - Retreats Aren’t a Luxury—They’re a Necessity: Reflections from Boulder and Why Retreats? - to dive deeper into why retreats matter and how they can transform your team.
Ready to design a retreat that’s as thoughtful as it is impactful? We’re here to help. Whether you need facilitation support, design guidance, or just someone to tell you what not to put on the schedule, we’ve got you covered!
Let’s make this summer’s retreat one your team won’t just remember but will grow from.
