How to Organize Your Own Artist Retreat

What I’ve learned from DIY retreats with creative friends

In my last post, I wrote about how I went from being an artist retreat skeptic to someone who now jumps at the chance to go on one.

Several people asked how the retreats I go on are actually organized, since most of them aren’t run by a formal retreat center. We usually just gather a small group of friends and structure them ourselves.

The good news is that organizing your own retreat doesn’t have to be complicated or expensive. With a little planning, you can create something that gives you many of the same benefits: space to think, time to work, and meaningful conversations with other creators.

A watercolor and ink illustration I did at a retreat a few weeks ago. I

Here are a few things that have helped make the retreats I’ve been part of successful:

The people

Choosing the right people is pretty key to a successful retreat. Of course, only go with people you like—or at least people you think you’ll enjoy being around.

I’d recommend a minimum of four people (so if one cancels you still have three). Two could work too, although it doesn’t quite have the same group dynamic. If I did it all by myself, I’m pretty sure I’d go nuts being all alone after a day or two. I’ve gone with up to 10 but the bigger retreats do require more organizational work.

I like to go with people who are at a similar professional stage as me since this creates more of a peer atmosphere. No one takes on the role of the expert, and we often have similar goals. When someone hits a roadblock, someone else has usually been through something similar.

Choosing the location

I usually try to find somewhere free or low-cost. The ideal situation is a cabin or second home that someone in the group has access to. I’ve also done retreats at an Airbnb, or rented part of a summer camp in the off-season.

Ideally, each person has their own private space to work, along with some communal areas for people who want social interactions.

I wouldn’t recommend hosting it at someone in the group’s primary residence. It’s hard for that person not to feel the pressure to host or deal with everyday responsibilities.

I also prefer locations within a few hours of where I live. My goal for a retreat is to work, think, and relax—not to be exhausted from travel or distracted by sightseeing.

Length of the retreat

I usually aim for three nights, which gives enough time to settle in, work, and still have space for conversation and rest.

I’ve also done two-night retreats, which can work well if that’s what people’s schedules allow. I’d love to go longer, but it can be hard for many people—especially those with families—to get away for extended periods.

Even a couple of days can make a real difference. Often it’s just enough time to step out of your normal routine and return home feeling refreshed and full of new ideas.

Proximity to nature

I love trees and wandering around outside, so being able to step outdoors somewhere beautiful is ideal.

I do a lot of thinking while walking, and nature keeps me from feeling cooped up.

Flexible structure

The most common retreat format I do is one where we share lunch and dinner, but mornings and afternoons are unstructured.

People use that time however they want: writing, making art in their room, going for a walk, reading a book, or sketching somewhere outside.

After dinner we usually gather to talk about what we’ve been working on, share work, and offer feedback if someone wants it. That’s my favorite part.

Clear expectations

It’s important to make expectations clear before the retreat.

One helpful thing is to have a short call with everyone beforehand. That way people can talk through the structure, responsibilities, and what they’re hoping to get out of the experience.

A friend of mine once thought he was going to a work-focused retreat and intended to get a lot of writing done, but it turned out everyone else was planning to party all weekend. He had writing deadlines, his computer broke, and he felt stuck there. Not ideal.

So it helps to clarify ahead of time:

• Is the retreat mostly independent work with shared meals and discussion in the evening? (This is usually the type I do)

• Are people planning group “field trips” to draw or write together?

• Is it more of a social hang with fellow artists?

• Does someone want to host a workshop or demonstrate a technique?

None of these approaches are wrong. But it’s much better when everyone arrives with the same expectations.

Personal intention setting

Before a retreat, I like to make a drawing or write a couple bullet points about my intentions for the experience.

Since I started doing this, I’ve enjoyed retreats much more. Setting an intention helps me remember what I actually want from the time.

I also usually make a pact with myself not to check email or social media while I’m there. That’s key for being present.

Handling food

We usually split up food responsibilities among the group so no one has to do the bulk of the work.

People handle their own breakfasts and snacks. Lunch is either something someone prepares or leftovers.

One or two people take charge of dinner each night and plan it ahead of time. I often cook my dinner at home and bring it with me so it just needs reheating—I don’t want to spend a lot of time cooking while on retreat.

A shared Google spreadsheet works well for planning meals so everyone knows what others are bringing—and you don’t end up with twenty avocados (true story).

Why it’s worth doing

For me, the biggest benefit isn’t just the quiet time to work. It’s the feeling of camaraderie—being surrounded by supportive creative friends who understand the challenges of making things.

Over the past couple years, these retreats have given me encouragement when I was stuck, smart feedback that helped move projects forward, and the deep support that comes from people who care about both you and your work.

That combination of solitude and community is rare in everyday life, and retreats create space for it to happen.

I’m curious: have you ever organized your own artist or writing retreat? Or is it something you’d like to try? Let me know in the comments!

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Take care and keep creating!

-Katharine