If I Were You, I'd Ask These Questions Before Booking Any Retreat (Including One of Mine)

Running a retreat company means asking people to trust a stranger with their money, their vacation days, and — depending on the retreat — their safety. I think about that a lot. So instead of writing something generic about "what to look for," I decided to just answer the questions I'd want asked of me. These apply to any retreat operator, not just ones that involve scuba — including yours truly.

Questions Worth Asking Any Retreat Operator

1. Does the person running this actually know the destination and activity firsthand — or are they working from research?

It's a fair question, and the honest answer is often "some of both." I've spent thirty years diving on my own dime across more than a dozen countries, learning what separates a genuinely good dive operation from one that just photographs well.

But as I keep expanding into new destinations, there will always be places I'm building a retreat around before I've personally dived them myself. For those, I rely on the same process I'd want any operator to use — deep research into resort reputation, guest reviews, and direct conversations with the people running the operation. Ask any operator which situation applies, and don't assume firsthand experience just because the marketing implies it.

2. What happens if it's cancelled — by you, or by them?

The refund details themselves should vary by resort and destination, because they depend on what the operator can actually recover from their own suppliers. What shouldn't vary is whether the policy is published somewhere you can find it — on the booking page itself, not just something you're told if you happen to ask.

If you have to request the cancellation policy directly instead of reading it upfront, that's worth noticing.

3. How big is the group, and does that actually match what you want?

This depends entirely on the type of retreat, and there's no universally right answer. Some people want to disappear into a bigger group; others want to know everyone's name by day three. Whatever the number is, ask for it directly — "small group" means something different to every operator.

4. Is participation in every included activity required, or can you opt out?

This is worth asking of any retreat, no exceptions. Some retreats are built around full immersion on purpose, and treat every session as part of the design rather than an optional extra. Others are more of a menu you pick from. Neither approach is wrong, but you want to know which one you're booking before you arrive, not after.

5. Does the process include any kind of conversation before you book?

A phone call or short interview before booking isn't standard across the industry, but it's worth asking about. It gives both sides a real chance to check for fit — the operator gets a sense of whether you're a good match for what they've built, and you get a much better read on them than a sales page ever gives you. If an operator offers this, even as an optional step, it's usually a sign they care more about the right guests than about filling every seat.

If the Retreat Involves Any Certification-Based Activity (like Scuba)

6. Is the activity itself run by a vetted, certified operation — or outsourced to a third party nobody's checked out?

Any retreat built around a certification-based activity should be able to tell you plainly whether the diving, climbing, or instruction is handled by a properly credentialed in-house operation, or subcontracted to whoever was available locally. Every dive resort I build a retreat around gets vetted for this before it's ever on the itinerary — ask any operator to confirm the same for theirs.

7. Does the actual daily schedule match what's advertised — for everything listed, not just the headline activity?

Picture a yoga retreat: most days, that's yoga, meals, sleep, maybe some journaling — and if that's genuinely how the days are structured, it's doing exactly what it promised. The point isn't whether one activity outranks another. It's whether whatever's listed as part of the experience actually shows up in real time on the schedule, and isn't just a line in the marketing copy. Ask to see an actual hour-by-hour day rather than a bullet list of "included" amenities — it's the fastest way to tell the difference.

8. What does the guest-to-instructor ratio actually look like for each activity?

A single "total guests" number doesn't tell you much, because ratios can differ a lot between activities within the same retreat. For ours, yoga runs as one instructor for the whole group, since that's appropriate for the activity — but diving is split into smaller groups of 3 to 5 divers per divemaster, since that's what the activity actually calls for. Ask any operator to break this down activity by activity, not just quote you the retreat's overall headcount.

None of This Guarantees a Perfect Trip

But it's a fair standard to hold any operator to — including the ones who haven't been asked yet. If you're curious how we answer these for our own retreats, you can see what's coming up on our Upcoming Retreats page.