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How to Find the Perfect Retreat for You

Getting ready to write this post, I was thinking back and trying to remember when my first retreat was—and I actually couldn't remember! I think I got used to the concept of a retreat by being eased into it: My earliest retreat experiences had a purpose, such as strategic planning for a student group in college or immersing myself in yoga anatomy education.

At some point I started signing up for retreats just for the sake of going on a retreat. By that time, I had already experienced the magic. I knew that with a change of scenery comes a new perspective. I had seen for myself how getting away from everyday responsibilities for a few days could result in insights and shifts that would last long after I returned home.

The first retreats I can recall going on were religious retreats, facilitated by Catholic clergy members, where we explored a specific topic over the course of a weekend. In 2010, I canceled my wedding just one month beforehand, and I found myself questioning how I had gotten so far down this road only to turn not just my own life, but also that of someone else I cared about, upside down. A friend and mentor told me that during a similar moment of reckoning in her own life, going on a silent retreat had brought about powerful transformation. After that conversation, suddenly it seemed like everyone was mentioning silent retreats and telling me I should go on one. I Googled "silent retreats near Boston," and out of the possibilities, one taking place at a Catholic retreat center on Massachusetts' North Shore stood out to me. I was worried that being alone in silence with my thoughts and emotions, with no distractions, might actually be quite an intense experience, and I felt that the familiar religious foundation would provide a touchstone to help me feel comfortable in this context I still wasn't sure about.

That silent retreat in Gloucester turned out to be hugely cathartic. I remember crying for several hours each day. It wasn't exactly pleasant, but I didn't feel sad or depressed—it felt like release and healing. I journaled. I read. I went for walks along the ice-crusted shoreline. I stared out the window watching cargo ships on the horizon. I remember how much more vivid the taste of my food and my tea seemed without having to divert some of my energy to conversation. Life seemed so much clearer without all the noise. That retreat moved me on a soul level. After that experience, I was hooked—and determined to make time and space for experiences like that, at least occasionally, in my life from then on.

The next one I remember (again, I may have gone on more that just aren't coming to mind right now!) was at the Kripalu Center in Massachusetts. I went to spend a weekend being taught by Tara Brach, whose book Radical Acceptance had been very influential for me.

In 2013, my husband and I sort of accidentally ended up on a yoga retreat together in Iceland. I say it was accidental because although we both wanted to visit Iceland, Sean wasn't necessarily interested in a yoga retreat—but he was willing to go to yoga class for one hour each day since it came with the package of being guided around to nature attractions and historic landmarks by a friend of mine (and fellow yoga teacher) who had visited Iceland enough to know local guides and refine her itinerary. It was an incredible experience and really showed me what a difference the setting can make to the feeling of a retreat. Iceland's unique geology and topography give it such a rugged and magical feel. I highly recommend visiting Iceland in general, and the retreat format felt so special compared to the usual guided tour format for visiting new places.

I'm only realizing as I write this that I put my vow to make time for retreats on the back burner for several years due to all the medical and fertility stuff that's consumed our attention. Last summer, heartbroken over a failed embryo transfer, I felt a need to get away from the pain and was also feeling bitter about how I'd put life on hold for fertility treatments and had nothing to show for it (at least that was how it felt at the time). I was also looking ahead to having a surgery that, while I hope it goes smoothly, could have serious complications for me based on past history.

Around this time, the enrollment deadline was coming up for a writing retreat in Costa Rica being hosted by a friend. I had spoken with her about it a few weeks earlier, but I wasn't able to commit due to the possibility of being pregnant (and still needing to perform daily injections, see a high-risk doctor, etc.). Once we got that negative test, I was determined: If I couldn't have a baby (at least this year), I was going to write a book.

That Costa Rica retreat turned out to be not only productive but transformative, and I found myself curious about creating retreats like that for other people. They had meant so much to me that I started to feel this was part of what I was meant to offer the world—creating experiences that would allow them to get away from the responsibilities of daily life and get in touch with their true nature and essential self. I started to turn over ideas in my head and talk to people who lead retreats (including my friend who organized the Costa Rica one). I wanted to learn what went into the process, and we also began to discuss potential future collaboration.

It was in this process that I ended up signing up for a yoga and coffee retreat in Colombia. My friend who organized that one had planned an itinerary for us to travel along Colombia's Caribbean coast several years earlier through the travel business she operated with her husband. I had seen on social media that she was now offering retreats, and I wanted to talk to her about the logistics of it—but when I saw on her website that she had listed a retreat that combined two of my biggest passions in life (coffee and yoga) I decided to go and learn firsthand how she created a retreat while also having the chance to discuss in person. This, too, turned out to be a magical experience with an abundance of insight and transformation—partly due to the very special location and partly due to an expertly designed program.

Since I've begun looking into organizing retreats (and thus I've been talking about it more), I've been getting questions about what I look for in a retreat and how people should go about choosing one if they've never been on one before (in addition to why they would want to go on one in the first place). The above recap of all the ones I've attended was meant to help explain how I've chosen the ones I have, but as I've been reflecting on it all, a few tips have come to mind that might help if you're just starting to explore the idea of going on your first retreat.

Use retreat listing websites as a starting point. If you Google "yoga retreats" or "writing retreats," you can find websites that aggregate retreat listings. Browse through the details and notice which ones stand out to you. Seeing the range of what's available will help you know what to look for when evaluating any single retreat, even if you don't end up going with one you find on these sites.

Pay attention to who the retreat is with and not just where it is. Although a beautiful location goes a long way toward creating a memorable experience, the facilitator can truly make or break the retreat. It's not so much about the retreat being "bad" as it is ending up with someone you personally don't mesh with or who isn't focusing on what you want to focus on. Your time is valuable, so if you're considering a retreat with a facilitator you don't have previous experience with, do some research into that person's work and overall vibe before booking.

Follow on social media and subscribe to newsletters of people you'd enjoy going on a retreat with. On that note, it may be worth waiting for an experience that's hosted by someone you know you want to travel with. If there are people whose work you enjoy and want to go deeper with, make sure you're connected with them to stay in the loop when they announce future offerings.

Pay attention to the details. I hesitated to include this one because I'd encourage you to "just go" rather than obsess over the details—but I'd also hate for you to have a bad experience that turns you off to further travels. The retreats I've been on have ranged from luxury to super bare bones, and I'm cool with either—but I know some people would have a trip ruined by having to share a room or sleeping in a tent that bugs make their way into no matter how well you zip it. So I'd just say to do your research on the accommodations and make sure you know what you're getting into. In addition, it's worth paying attention to the itinerary, or asking for a copy of it if it's not posted. How will the days be structured? Will they be heavily scheduled or allow lots of time for reflection—and how does that compare to what you want?

Don't be afraid to ask questions. If there's a retreat that looks good to you but you're not quite sure, don't hesitate to reach out to the facilitator and ask questions. When teachers offer programs like this, we put our hearts into them, and I think most of us would be more than happy to get on the phone with you and answer questions. It's really not about selling—we want participant and leader alike to feel it's a good fit because that's what creates the best experience!

But also don't be afraid to go with your gut. In contradiction to everything I just wrote about doing your research and asking questions, sometimes you do just have to go with your instincts! This is how some of my best retreat experiences have come about. In one case I knew almost nothing about the facilitator, the itinerary, or the location. I just had a feeling it would be magical—and that feeling turned out to be so right! There are times in our lives when impulsive decisions make sense, and if you're in a stage like that you should feel free to disregard all the previous points about doing your homework—just leap and the net will appear.

When was your first retreat? Or are you still contemplating booking your first one? Please leave a comment below or email me at—I would love to know your thoughts on this post as well as what you think makes for a good retreat! And if you'd like to get updates about opportunities to go on a retreat with me, you can sign up here to get notified.

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