Guides for hosts
How to plan and run a retreat
This section covers everything that happens between "I'm doing this" and the last guest going home: the offer, the budget, the dates, the venue, the itinerary, and the money and legal pieces that hold it all together. Below is the order I use on every retreat, the guide for each piece, a free checklist, and two podcast episodes where Robert, Stacy and I talk through the parts hosts get wrong most often.
How do you plan a retreat?
In order, roughly:
- Who it's for and the offer. Decide who you're inviting and what they get before you decide anything else.
- Budget and price. Know your real cost per guest, deposits and all, before you set your ticket price.
- Dates, and how far ahead to launch. Your runway shapes almost every decision that follows.
- Venue. What fits the group size and the budget you just set, not the other way round.
- Itinerary. What actually happens, day by day, once people arrive.
- Contracts, deposits and cancellation. What protects you, and what protects your guest.
- Insurance and waivers. Coverage for you, and coverage you require of them.
- Registration and booking. How people actually sign up and pay.
That's the framework. Each step has its own guide below.
What to decide first
Start with who it's for and your budget, because almost everything else depends on them. Your deposit depends on your budget: you can't set a fair deposit until you know what you owe vendors before the trip even starts. Your sales page and your launch plan depend on your date: you're working backwards from the day guests arrive, not forwards from whenever you happen to feel ready. And your date depends on your venue, because the venues worth booking are usually reserved further out than new hosts expect, especially for a group.
Settle those three, in that order, and the rest of the list stops feeling random. Pick a venue before you've decided who you're inviting and what they're paying, and you'll end up with a place that doesn't fit the group you actually attract, or a price that doesn't cover what the venue costs.
Every guide in this section
- Choosing a retreat venue: how to pick a venue that fits your group size and your budget, not the other way round.
- Writing a retreat itinerary: how to build the actual schedule for the week, from arrival to the last session.
- Retreat contracts, deposits and payment plans: what to charge upfront, what to charge later, and why.
- Your retreat cancellation policy: what happens when a guest, or you, has to pull out.
- Retreat insurance and liability waivers: what covers your guest, and what covers you.
- Retreat registration and booking software: how people actually sign up, pay, and get reminded.
- Hosting a retreat abroad: what changes about contracts, payments and logistics when you're not hosting in your own country.
- The retreat planning checklist: every step above, in one list, in order.
The free planning checklist
If you'd rather have all of this in one document before you read another guide, we built The Other Half, a free checklist that walks every stage in order, in eight sections. It's the same shape as the list above, just longer and more specific.
From the podcast
Robert, Stacy and I talk through a lot of this out loud on the podcast, and two episodes line up directly with this section. Episode 3 is about deposits: how big a deposit should be, what a deposit tells you about who's serious, and why I've never changed my approach to it. Episode 4 is about how far ahead to plan: my rule of thumb is six months minimum from launch to your start date, and nine to twelve months if you're new to hosting. Robert said something in that episode I still think about: he'd rather get a percentage of something than a hundred percent of nothing, which is really an argument for not trying to plan your first retreat entirely alone.
Join The Community
Weekly office hours with me, Robert or Stacy, and the Library's planning, venue and legal shelves, open the day you join. Join The Community for $99 a month, or lock in the founding rate of $49 a month, for as long as you stay a member, if you join before December 31, 2026.
Questions hosts ask
How far in advance should you plan a retreat?
Six months minimum from launch to your start date, and nine to twelve months if you're new to hosting. A shorter trip with an audience that already knows you can work on the shorter end; a longer or more expensive trip needs more runway, because people need time to clear a calendar and save money, and you need time to sell it without sounding desperate.
How much does it cost to host a retreat?
It depends on your venue, your group size and what's included, but most first-time hosts underbudget it. Add up your real cost per guest, deposits and all, before you set your price, not after you've already told people a number.
Do I need insurance to host a retreat?
You should carry your own liability coverage as the host, and you should require your guests to carry travel insurance that covers cancellation. The two protect different people: yours protects you and your business, theirs protects the deposit they paid you. Requirements vary by where you're hosting and what you're doing, so this isn't legal or insurance advice. Check with a licensed insurance agent and, if you're unsure, an attorney before you finalize coverage.