Paddling with Perfectionism
A surf retreat to cultivate pleasure, presence, and play!
Welcome to the retreat where your inner overachiever gets to chill.
Join us in Costa Rica to explore what it means to live with perfectionism, without letting it run the whole show. Think less hustle, more hammock. Less pressure, more pleasure. Through group workshops, joyful movement, and a week on your surfboard, we’ll practice what it’s like to show up fully as you are, not as your resume, your to-do list, or what your inner critic says you “should” be.
This isn’t about fixing your perfectionism—it’s about paddling with it. Your drive, ambition, creativity, and passion are beautiful parts of who you are. During our time together, we will learn how to celebrate these gifts, while also learning how to avoid burnout, or feelings of discontentment because things aren't "perfect".
During our week together, the ocean will be our teacher, inviting us to move with curiosity instead of control, and cultivate play, pleasure, and power by living in the present moment. Whether you’ve never touched a surfboard or you’re just here for the sisterhood and self-discovery, Paddling with Perfectionism is your invitation to reconnect with your body, your joy, and the part of you that knows how to play.
Join us March 8th through 14th, 2026 in Jacó, Costa Rica.
This is an all-inclusive retreat that is geared toward beginner surfers. This experience has been designed for a group of 8 to 10 women in order to foster connection, safety and individualized care. Throughout the week you will be supported by experienced therapists and surf instructors.
Create a deeper connection to yourself, your body, a community of surf sisters, and Mother Ocean through a week of adventure and surfing, workshops, and connection.
There is a limited number of spots available. Registration opens April 30th. Don’t miss your chance to join us for this transformative experience.
7 days/6 nights at Hermosa Jungle Land Resort just 12 minutes from the beach
All meals and snacks are provided by a private chef
5 surf lessons with individualized, professional instruction
Surf video analysis and photography
All surf equipment
Two yoga and meditation sessions
Daily group mindfulness activities
Customized surf swimsuit by Marveca Beachwear!
Therapeutic workshops led by 2 licensed therapist
Surf Journal
Local adventures (viewpoints, waterfalls, hikes, town visits)
Group Transportation to activities
Group Transportation to and from San José Airport
2 Pre and 1 Post Zoom calls for pre trip planning and continued community support after the trip
Pre trip planning guide
A therapeutic hand to help you tailor this experience to your life circumstances
A community of badass women who are living life courageously, too
Can't be beat views and immersion into Costa Rica's wildlife
Not included: international airfare, travel insurance, additional activities
What’s Included
Meet your hosts
Kristen and Kristin are friends, fellow perfectionists, and therapists with a love for the outdoors.
-
Kristen Ales is a licensed professional counselor, registered supervisor, and the owner of Wilder Wellness, a virtual group practice serving individuals based in Oregon. Wilder Wellness helps their clients build confidence, connection, and trust in the relationship they have with their bodies so they can take on any adventure.
Kristen has worked as a wilderness guide and group facilitator for the last 14 years. She believes that the time she has spent in the outdoors played a significant role in her own recovery from disordered eating, which inspired her to pursue a career in mental health.
Kristen received her masters in Clinical Mental Health Counseling with an emphasis in Wilderness Therapy from Naropa University. Since graduating, she has led multiple size-inclusive outdoor adventure retreats all over the world. Her retreat work has been featured in various media outlets including Outside Magazine, Self, and She Explores.
Outside of work, you can find Kristen chasing her one-year-old Poppy, spending time with friends and family, cooking, watching anything on the Bravo network, and of course playing outside.
-
Kristin is a licensed trauma informed, somatic therapist, just-for- fun surfer with soul connection to nature and adventure. She operates Emerge Surf and Somatic Therapy a therapy practice from both the USA and Costa Rica offering individual therapy and group community surf therapy.Kristin supports women in healing from trauma, PTSD, and anxiety by reconnecting to the wisdom of our bodies, our communities, nature, and rediscovering personal freedom.
She's a trained surf therapy facilitator by Groundswell Community Project the first ever surf therapy training program approved by a therapy association. She loves facilitating group experiences that help us reconnect with creativity, joy, play, and freedom.
She's been all over the world in her personal and professional adventures and now enjoys creating experiences for other women to rise!
Check out this video to learn about our take on perfectionism and what to expect on the retreat!
FAQs
-
We ask that everyone arrive at San José Airport (SJO). We’ll arrange group transportation from the airport to our lodging at Hermosa Point Resort.
-
Yes! This retreat is designed with beginner or new surfers in mind. We’ve teamed up with a professional surfing school to offer 2:1 instructor: student lessons, individualized to your comfort level and abilities.
-
Packing and preparing for trips can bring on a lot of stress! We have created a Pre Trip Planning Guide that you will receive 3 months prior to our trip that includes trip logistics, a detailed packing list, and our recommendations to best prepare yourself to travel.
-
An initial deposit is required to secure your booking. The remaining balance is due 90 days before our trip so that all activities, services, and support can be confirmed. Individual payment plans will be discussed after your booking and deposit are secured.
-
Since this is an intimate, smaller group experience there is a non refundable deposit required to secure your spot and commit to this experience. We will discuss individual payment plans for covering the rest of the cost by 90 days prior to your trip. If cancellation occurs before 90 days before the trip refunds will be made available on payments additional to the non-refundable deposit. If cancellation happens within 90s of the trip the full booking becomes non- refundable.
-
All participants are highly recommended to obtain traveler insurance within 14 days of signing up. While we don’t hope emergencies happen, we want you to feel prepared if they do. Travel insurance will help cover the cost of travel emergencies, last minute trip cancellations due to illness or injury, environmental emergencies, lost luggage, or medical emergencies while away from home.
-
Not at all!
This retreat is an opportunity to connect with others, share experiences, offer support, and gain different perspectives under the guidance of a licensed therapist. When paired with our breathtaking location and surfing experience, you’re set up to build lasting relationships with each other and deepen your understanding of yourself.
-
No problem at all! Send an email to kristen@wilderwellness.co and kristin@emergewithfreedom.com and one of us will get back to you within 48 hours!
Pricing
There are two different pricing options, and we offer long-term payment plans. Choose between a private bungalow or a shared suite, each with an ensuite bathroom, viewing platforms of the surrounding jungle and the ocean, and two private pools.
Shared Bungalow: $3,499 USD
Private Bungalow: $3,999 USD
The deposit to save your spot is $1000 at the time of booking. You can view a sample payment plan here.
Note: You will be directed to the Emerge Surf Therapy website for booking.
Cancellation policy
Since this is an intimate, smaller group experience, there is a non-refundable deposit required to secure your spot and commit to this experience. To help eliminate any financial stress, we offer individualized payment plans for covering the rest of the cost by 90 days before your trip. If cancellation occurs before 90 days before the trip, refunds will be made available on payments in addition to the non-refundable deposit. If cancellation happens within 90 days of the trip, the full booking becomes non-refundable.
We Highly Recommend Travel Insurance
All participants are highly recommended to obtain travel insurance within 14 days of signing up. While we don’t hope emergencies happen, we want you to feel prepared if they do. Travel insurance will help cover the cost of travel emergencies, last minute trip cancellations due to illness or injury, environmental emergencies, lost luggage, or medical emergencies while away from home.
We want you to be able to sleep well at night knowing that you're protected from unexpected costs can occur with travel these days. Plus, since your retreat package is non-refundable after a certain point, trip cancellation and additional CFAR ("cancel for any reason") benefits may reimburse you if you become sick or injured and can't travel. (Please check the specific terms and conditions of your policy, however, for details about any specific scenarios. We cannot guarantee coverage from third-party insurers).