Why the Best Retreats Don’t Feel Like Conventions
There’s a familiar version of the retreat or offsite: hotel ballroom, coffee urns, breakout sessions, PowerPoint decks and a setting that could be almost anywhere.
Sometimes that model works. A lot of the time, it doesn’t.
The biggest problem isn’t that it’s boring. The biggest problem is that it often fails the most important test people now apply to any in-person gathering:
Did this really need to happen in person?
That’s a tougher question than it used to be.
Hybrid work changed expectations. Virtual tools got better. Distributed teams became normal. Travel budgets became more scrutinized. At the same time, in-person gatherings did not disappear. In fact, business travel remains substantial, and offsites continue to matter. GBTA’s 2025 outlook says global business travel spending grew to $1.47 trillion in 2024 and is projected to reach a new high in 2025, while Emburse reports that average annual company offsites increased from 2.4 in 2019 to 2.6 in 2024, with the share of companies holding no offsites dropping sharply.
That pressure is healthy.
It forces leaders and operators to be honest about what in-person gatherings are for.
If a meeting can be replaced by a webinar, a slide deck or a few Zoom calls, then maybe it should be. But if the real value comes from trust-building, shared experience, strategic clarity, team connection, or simply getting people fully present with one another, then the physical setting matters a great deal.
That’s where certain retreat models have an edge.
In my view, retreats are different. You’re not just selling meeting space. It’s not really about meeting space at all. You’re selling experiences. And when you’re selling experiences, context is king.
Ballrooms are interchangeable. People feel that, whether they express it or even consciously notice in the moment. Places with a stronger sense of setting — open air, trails, creeks, porches, fire pits, views, room to walk, room to exhale — do something different. They lower the temperature. They make conversation easier. They create the conditions for people to stop performing and start participating.
That is not anti-business. It is good business.
The meetings and events industry increasingly recognizes that “human connection” is central to the category, not just a soft extra. At the same time, the outdoor-hospitality sector continues to benefit from durable consumer demand for nature-based experiences. KOA’s latest outdoor-hospitality research points to continued interest in camping and outdoor travel, including from younger travelers looking for connection, wellness, and experience-driven trips.
Put those shifts together and a clear pattern emerges.
The retreat formats with the most insulation right now are the ones that understand they are not just hosting a meeting. They are creating an experience that can’t be replicated through a screen.
They are creating the chance for a leadership team to have the conversation it has put off for six months.
They are creating the chance for distributed employees to feel like an actual team.
They are creating the chance for families or groups to step out of a hyper-managed, hyper-digital routine and do something that feels more grounded.
And importantly, the best of these experiences feel inviting rather than intimidating.
That point matters to me. A lot of outdoor spaces and brands have historically made the outdoors feel like a club — if you already know the rules, have the gear, and speak the language, you belong. If not, you don’t.
I think the better opportunity is to make the outdoors more accessible.
Not watered down. Not fake. Just more welcoming.
The best retreat and outdoor-hospitality concepts do exactly that. They reduce friction. They help people feel comfortable quickly. They create enough structure to make the experience work, but not so much structure that the whole thing feels overly programmed.
That balance is hard to get right. But when you get it right, the experience becomes much harder to dismiss as optional.
Nobody says, “This could have been a webinar,” after a genuinely useful day outside with a team or family in a place that changed how they felt and how they interacted.
That is the edge.
Not every retreat needs to happen outdoors. Not every group wants the same thing. But I do think the category is moving toward experiences that are more rooted in place, more human, and less interchangeable.
In a world where information is everywhere and virtual access is easy, the thing that stands out is not content alone.
It’s the quality of the experience around it.
— Ryan Tyrrell is a Nashville-based entrepreneur and operator with experience building businesses in consumer services, hospitality, digital products and community-focused ventures. Follow Ryan on Substack.
Further reading:
· Business Travel Index Outlook (GBTA)
· The State of Corporate Offsites (Emburse)
· Camping and Outdoor Hospitality Report (KOA)