How do You Organize a Retreat? - Wanderlust Entrepreneur | Business + Retreat Coaching for Retreat Leaders | Sheri Rosenthal
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A group of people eager to travel with you. 
One picture-perfect destination. 
A list of jaw-dropping activities. 
These are all vital elements to organizing a retreat. 

Are you left scratching your head wondering how to put them all together? 

Organizing a retreat is a big deal.  It’s not like a birthday party you just throw together.  To go off without hitch and be a roaring success, a retreat needs to be envisioned, planned, and executed with the same precision as an elite athlete prepares for a race.  So, make sure to strap your sneakers on extra tight because this race is an endurance one.

There are big tasks to tackle.  Tiny details to wade through.  And everything in between.  The reward is high, and the risk is too.

There’s no need to fear, though.  It’s just a matter of being clear.  You want to pause, take a deep breath, and connect first to your why.  Why do you want to plan a retreat?  What is bringing you to this opportunity?  The better you connect inside with what is fueling you, the more likely you’ll stay motivated for the long haul as you take your retreat from an idea to an idyllic event.  Ahh…

After you connect with your why, you then want to make sure you get strategic with your retreat organizing.  After all, organization is key! 

Here are our top three keys for how to organize a retreat, Wanderlust Entrepreneur style:

Step 1: Lay out a well organized timeline

The first key in organizing a retreat is to come up with a timeline.  Retreats take careful research, planning and preparation.  You need ample time to do all that.  A minimum of six to twelve months is our recommendation.  The more time the better.  And, if it’s your first time organizing a retreat, do yourself a huge favor and plan at least a year out.  That may sound like a lot of time.  Trust us though, it’ll go by fast.

With your timeline in place, you’ll then want to organize a step-by-step process of how you’re going to take your idea and make it a reality.  The key here is to write out the tasks you must complete to organize your retreat.  For example, these might appear on your list, among others: choosing your location, booking your venue, coordinating your meals, securing transportation, researching activities, and reserving those activities.

Once you have your list made, you’ll then want to assign a window of time to start working on each task.  Since choosing a location and booking a venue are top priorities, you’ll want to put them at the top of your list and handle those first.  If you’re organizing your retreat planning one year out, this means you’re researching a location and booking that venue first!  It’s all about focus!

As you scratch off these top priority tasks, you can then move on to others all the while sticking to your list and timeline to make sure you’re dotting all your i’s and crossing all your t’s.

Step 2: Design a deeply transformational theme

The second key in organizing a retreat is to have a solid theme.  Without a core idea to plan your retreat around, your trip is likely to fall flat, sounding more like a vacation in a pretty place than a high-value, transformational experience.  Keep in mind this rule of thumb: vacations, while wonderful and full of rest and self-care, sound optional.  Powerhouse transformational experiences that solve a person’s pressing problems, on the other hand, sound necessary.

When you have a theme in mind, you can then set your retreat up to deliver on that theme.  If you’re a woman in her 50’s who wants to go on a retreat to discover how she can eat healthier, which retreat do you think you’re more likely to choose?

Option one: a “Fun in the Tuscan Sun” retreat at an Italian resort that will feature a healthy twist on Italian food.

Option two: a “Fifty, Fit & Fabulous” retreat set at an intimate bed & breakfast in Maui, Hawaii where the proprietor of the inn will prepare good-for-you meals while you watch and learn quick kitchen tips?

The answer is clear.  The Maui retreat!  It’s not only tailor-made for you, but it has a solution built into it (learning how to prepare healthier meals).  Get it?

With a clear theme in place, you can then plan experiential activities around that theme that will help deliver on the transformation you’re offering.  Taking the same example above, it would be better to plan a hike into the Haleakala crater (the largest dormant volcano in the world) than an art class at a local pottery studio.

While both would be fun, the hike involves physical exercise which is more aligned with the theme of the retreat.  Plus, that same hike could be turned into a powerful transformational moment by setting an intention for the hike and doing a group ritual once the destination is reached to seal the intention.  That’s no ordinary hike!

Having a theme for your retreat is like putting gas in your car.  It drives better.  Vroom vroom!  So, the next time you find yourself getting ready to plan a retreat, make sure you pause and decide the who & the what of your retreat.  Who is it for and what pressing problem does it solve?  This will not only make your organizing your retreat planning so much easier – but it will also set your trip up to be a problem-solving, transformational experience your people will have no choice but to say “yes” to.

Step 3: Protect yourself before you wreck yourself

The third key in organizing a retreat is to protect yourself before you wreck yourself.  These words may be tongue and cheek but seriously, we mean business.  You MUST make sure you are legally protected before you take people anywhere.

Here, liability forms are your best ally.  In our view, having these signed by your participants well before your departure date is a critical component to properly organizing your retreat.  Otherwise, you’re at risk, big time.

People in the United States are “sue happy” (a funny phrase meaning they like to file a lawsuit whenever any little thing goes wrong).  If something goes wrong on your retreat, you’re not immune from being hit with a lawsuit out of the blue (lawsuits are a common thing, here).  However, if you have your people sign comprehensive liability forms before your departure date, the forms provide a layer of protection should you be sued later.

Now, we know many of you live in countries outside of the United States and may be thinking “nope, not here.  We don’t sue in my country like in the United States.”  That may be true.  And, if you are having at least one person from the United States on your retreat, then you are not immune.  They could sue, as could anyone else. In addition, make sure you are fully insured with professional and general liability insurance as well as retreat insurance if you can get it.

The bottom line is this: you want to go out of your way before you leave for your retreat to make sure you have your legal ducks in a row.  If something goes wrong on your retreat and someone gets injured or has a problem, you’ll be happy to have peace of mind courtesy of the insurance and liability forms you had everyone sign weeks – if not months – before they boarded the airplane.

Ahh, peace of mind of properly organizing your retreat.  We love the sound of that.  And we bet you do, too, wanderluster.

Just in case you are looking for an excellent step-by-step checklist for your retreat planning, we have a 5-page comprehensive list that is simply life-saving! You can get all the details here.

Melanie ScottTo your wanderlust life & business,
Melanie Scott, Retreat Blueprint Coach @ Retreat Blueprint Program

As a self-proclaimed retreat-junkie, Melanie knows firsthand the power and transformation of traveling with a group of like-minded people who are ready to dive deep into themselves.  It’s pure magic! 

Melanie has planned, co-facilitated and attended dozens of retreats all over the world and is beyond excited to help other retreat enthusiasts do the same.  As a Retreat Blueprint Business Coach & Copywriter, Melanie specializes in helping retreat peeps crank up their businesses & add sparkle to their offerings so they shine to the cosmos and back.  

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