April 7, 2026
It was two hours before a private catamaran charter out of Simpson Bay. Twelve guests, full boat, paid in full. Then the message came in: "Hi, there's been a change of plans for our bachelorette party. We need to cancel. Can we get a full refund?"
Two hours. Crew was already there. Ice on board. I had turned down two other inquiries that week for the same slot.
I didn't have a written policy at the time. Not a real one. I had a vague sentence in a confirmation email that said "cancellations may be subject to fees." So I had a conversation I didn't want to have, gave back most of the money, and learned something I should have learned years earlier: a vague policy is not kindness. It's just delayed pain.
Most operators write cancellation policies the way they write waivers - once, reluctantly, hoping no one ever reads them. Then a cancellation hits, and they either enforce something guests didn't really agree to, or fold and eat the loss.
What I've come to believe - and this took me too long to figure out - is that a firm, readable cancellation policy doesn't drive guests away. Guests who read a clear policy and book anyway are the guests who actually show up. The ones who push back hard on your terms before booking are the ones who would have caused you problems regardless.
A wishy-washy policy trains guests to negotiate. A firm one with a human-sounding weather clause earns respect.
You do not need a legal document. You need three clear tiers and one weather rule. Here is the structure I'd suggest, and that I've seen work for operators across the islands:
The 50% middle tier is the part most operators skip, and it costs them. Without it, you either give everything back (too soft) or nothing (feels harsh). The middle tier is where you stop the bleed without feeling like a villain.
Weather is where policies fall apart. Guests think any clouds mean free cancellation. Operators know you can run a perfectly safe tour in light rain. Both sides feel the other is being unreasonable, and it turns into a mess.
The fix is to be explicit about who makes the call and what happens in each scenario. Here is the version I use:
One line worth adding: "If we cancel due to weather, we will contact you by email and WhatsApp at least two hours before departure whenever possible." That sentence cuts half the angry messages. People can handle a cancellation. What they hate is silence.

A policy buried in your terms page doesn't exist. Legally it might, but operationally it doesn't, because no guest read it and no guest feels bound by it. And if they dispute the charge, you need proof they saw it before they paid - not proof you had it somewhere on your website.
Place the short version of your policy in three spots:
When a guest disputes a charge, you don't get to explain yourself to the bank. You win with documentation. A checkbox timestamp and a confirmation email trail are what win those disputes.

For a long time I handled cancellations case by case. Someone had a good reason, I gave them a full refund. Someone seemed upset, I gave them a full refund. I told myself this was good guest service. What it actually was: a policy with no policy. Every cancellation became a negotiation, and I was always starting from behind because the guest knew I hadn't committed to anything in advance.
When I finally wrote a proper three-tier policy, published it clearly, and started enforcing it - something unexpected happened. The complaints went down, not up. Guests would read the policy, book anyway, and then when something changed they'd write in saying "I know it's inside 48 hours, I just wanted to ask." That "I know" is the whole thing. When the policy is clear, even guests who push back a little understand they're asking for a favor, not demanding their rights.
If you're on Junglebee, you can attach your policy to every booking confirmation and surface it in the checkout flow automatically - the checkbox and the paper trail without building anything yourself.
You can hold a firm policy and still be a generous host. Those are not opposites. When your terms are clear, you actually have more room to make goodwill exceptions without anyone feeling like you owe them something - because the baseline is already established.
The bachelorette party that cancelled two hours before my Simpson Bay charter? I refunded half - not because my policy said to (I didn't have a proper one yet), but because it felt right. I've had the same situation since, with a real policy in place, and the conversation took thirty seconds instead of thirty minutes. They read the terms before they booked. And when I offered to reschedule instead of a refund, they took it.
Write the policy. Put it where guests see it. Make them check the box. Then enforce it consistently, with one sensible weather exception you control. That combination - not flexibility, not leniency, not hoping for the best - is what turns your calendar from a source of anxiety into something you can actually predict.