THE COURAGEOUSLY PLAYFUL WOMAN RETREAT:
A retreat in Puglia, Italy for women who give so much, they forget how to receive.
September 12-17, 2027
You give so much. When was the last time you let yourself receive and fully rest?
You show up for everyone. Family, friends, work, the people who need you.
You're the one who holds it together, who handles it, who figures it out.
But somewhere along the way, you stopped being on that list.
And the version of you who knew how to rest, play, and just be without earning it first has been waiting a long time to come back.
Maybe you…
Take care of everyone, but rarely let anyone take care of you
Feel like you have to earn rest instead of simply needing it
Have a hard time saying no, even when you are stretched too thin
Have tried meditation apps, weekend getaways, even "self-care Sundays," only to feel like they don't truly make a difference
You’ve tried everything to feel better, but nothing seems to stick.
So you tell yourself it'll get easier once things calm down, once everyone else is okay, once you finally have a minute to breathe.
But the truth is, always being the one who shows up has quietly disconnected you from yourself.
The part of you that knows how to play, how to rest, and how to simply enjoy life has been waiting a long time to be let back in.
The Courageously Playful Retreat can help.
Our wellness retreat in Italy is an ideal setting with expert support to guide you towards joy and meaningful change.
This isn't just another wellness retreat or a temporary break from your busy life. It's a chance to truly reconnect with the part of you that you've neglected: your joy, your creativity, your playfulness, and your ability to live in the moment without needing to achieve something to feel worthy.
Through a unique combination of beginner friendly somatic healing practices, creative exploration, playful activities, and inner child work, this retreat is designed to help you:
Let go of perfectionism and reclaim your right to rest and play.
Heal the wounds of your inner child, allowing you to feel lighter and more at peace.
Reconnect with your body and emotions in a nurturing, supportive environment.
Create lasting shifts in the way you approach life, work, and relationships.
We move gently here. Nothing is forced. Everything is offered as an invitation.
It’s time to stop just surviving and start playing again.
Hi, I’m Dez.
For over a decade I have helped hundreds of women, supporting them through the process of healing trauma and breaking free from perfectionism and burnout, using somatic practices like yoga, breathwork, mindfulness, expressive arts, and guided imagery.
I have been running retreats for years, supported by a dedicated staff to make sure you get the attention you deserve.
Together, we’ll create a nurturing space where you can explore your past, let go of problematic over-functioning behaviors, and find new ways to embrace play and joy.
For high-achieving, over-functioning women struggling with perfectionism and the pressures of overwork, being courageously playful is a radical act of self-liberation.
In this wellness retreat in Italy, we'll be doing exactly that: stepping outside of rigid expectations, challenging deeply held beliefs about worth, and returning to a state of joy and freedom.
Here's how we'll spend the week together:
We'll gently work through your past, helping you understand the patterns that taught you to over-give and under-receive.
We'll come back into the present, using play and creativity to reconnect with joy and freedom of expression.
And we'll look ahead, so you leave with real boundaries and a lighter way of living.
What makes the Courageously Playful Retreat special?
Inner Child & Parts Work:
Compassionate, guided experiences to reconnect with the younger parts of yourself that learned love had to be earned. Together, we'll create space for healing and a deeper sense of worth beyond what you do.
Expressive Arts:
Painting, drawing, writing, and visual journaling to explore your inner world with curiosity. These practices help you connect with feelings that are hard to access through words alone.
Trauma-Informed Somatic Practices:
Guided yoga, breathwork, meditation, and nervous system regulation to help you slow down, come back into your body, and build a felt sense of safety and ease.
Nature and Awe:
Immerse yourself in the timeless beauty of Puglia's countryside. Wander among centuries-old olive groves, savor the quiet of the vineyard, lounge by the pool, and soak in the slow rhythms of Southern Italy.
Beach Excursion:
A full day on Puglia's coastline, where white sand meets turquoise water. Relax, swim, and reconnect with rest and simple joy.
Hands-On Cooking Experience:
Learn to make traditional Puglian orecchiette by hand. A sensory, unhurried experience that ends with a homemade meal shared together.
Is this retreat for you?
This retreat is for you if:
You feel like you have lost touch with the joyful, playful parts of yourself
You know something needs to change but you are not sure where to start
You are curious about somatic or body-based healing and want a safe, guided entry point
You have done some talk therapy but want to try something that works with the body, not just the mind
You want to be in community with other women who are also figuring it out
You want rest and restoration alongside reflection, not just one or the other
This retreat is NOT the right fit if:
You are looking for a deep dive into advanced trauma processing or extensive parts work. (That is what The Soul of Service Retreat is for.)
You are hoping for a quiet, private getaway with no group participation.
Let's get into the big details…
Who: A Group of 12 women from all over who want to heal and create a meaningful shifts in their life. Also, Dez (and her skilled team of professionals) as your guide on this journey.
(We know it can be scary to travel to a new place with a group of strangers, but we have so many women from past retreats who have made lifelong connections, because we are all here with the same purpose and the same goal)
What: 5 night / 6 day transformational wellness retreat.
When: September 12-17, 2027.
Where: A stunning private villa in the Puglia region of Italy. Nestled in the heart of Salento, our private villa is a beautifully restored 18th-century farmhouse surrounded by vineyards, olive groves, orchards, and rolling countryside. Rich in history and authentic Italian charm, the villa offers a peaceful retreat where rustic elegance, handcrafted details, and breathtaking views invite you to slow down, reconnect, and savor the beauty of Southern Italy.
Your tuition will include:
Thoughtful support every step of the way. From the moment you register, you'll receive personalized support to help you feel prepared and connected. Enjoy a detailed travel guide and itinerary, a pre-retreat Zoom meet-and-greet with fellow guests, and access to a private WhatsApp group for questions, updates, and community connection before, during, and after the retreat.
Round-trip airport transportation from Bari Airport. From the moment you arrive until we drop you off at the end of the retreat, we'll take care of the logistics so you can relax and fully settle into the experience. *** To help avoid the stress of unexpected travel delays, we strongly recommend arriving in Bari no later than September 11, 2027 (at least one day before the retreat begins) and departing no earlier than September 18, 2027 (at least one day after the retreat concludes).
All meals and snacks provided when on onsite at the villa.
Daily somatic practices such as yoga, breathwork, meditation, and visualizations.
Daily guided workshops including inner child, parts work and expressive arts using a variety of art mediums.
Excursion 1: Beach Day on Puglia's stunning coastline, where white sand meets turquoise water.
Excursion 2: A hands-on cooking experience where you will learn to make traditional Puglian orecchiette by hand.
Welcome gift: Receive a curated welcome package to support your rest and reflection throughout the retreat.
A safe, trauma-informed space: Every part of this experience is held with deep care, clear boundaries, and respect for your pace. You’ll be part of a small, intentional group of 12 women, each on her own journey to rest, restore, and create lasting change.
***Please note, what is not included:
Airfare to and from Italy.
Food, drinks, or any shopping you do on your free time.
Massages are available at an additional cost.
Travel insurance, which is required for each guest.
Rooms & Investment:
We created several room options so you can choose what feels supportive.
Mandorlo, Shared (sleeps 3)
A spacious suite with three twin beds and overlooks the vineyards, courtyard, and swimming pool. The space offers a calming atmosphere designed for rest and relaxation, along with modern comforts including air conditioning and an extra-large bathroom featuring a beautiful stone soaking tub.
$3500/person
Mitro, Shared (sleeps 2)
Two twin beds and beautiful views of the countryside, vineyard, and peaceful courtyard. The space offers a calming atmosphere designed for rest and relaxation, along with modern comforts including air conditioning, a rain shower, and plush bathrobes and slippers.
$4150/person
Limone, Shared (sleeps 2)
Two twin beds and independent access to the garden with beautiful views of the vineyard. The space offers a calming atmosphere designed for rest and relaxation, along with modern comforts including air conditioning, a rain shower, and plush bathrobes and slippers.
$4150/person
Melograno, Shared (sleeps 2)
A spacious suite with two twin beds, and living room with fireplace. The space offers a calming atmosphere designed for rest and relaxation, along with modern comforts including air conditioning, a rain shower, and plush bathrobes and slippers.
$4150/person
Ulivo, Private (sleeps 1)
This private room features a queen bed and a private terrace with sweeping views of the vineyards and olive groves, creating the perfect setting to enjoy breathtaking sunsets. This room offers a sense of personal sanctuary with modern comforts including air conditioning, a rain shower, and plush bathrobes and slippers.
5000/person
Malva, Private (sleeps 1)
This private room features a queen bed and a private terrace with sweeping views of the vineyards, where you can welcome each day with a breathtaking sunrise. This room offers a sense of personal sanctuary with modern comforts including air conditioning, a rain shower, and plush bathrobes and slippers.
$5000/person
A $500 deposit is required to reserve your spot. Payment plans for remaining balance will be scheduled for you once your registration/deposit are complete. Full tuition is due by August 1, 2027.
All tiers include everything listed above. Very limited spots in each category.
Is this your first time doing something like this?
Most of the women who come to Courageously Playful have never been on a retreat like this before. Some have never done any kind of somatic or expressive arts work. Some traveled alone for the first time to get here.
What they all have in common: they showed up anyway.
We do everything we can to make that easy…. Small group size so you are not lost in a crowd. A structured arrival process so you know exactly what to expect. Clear agreements at the start of the retreat so everyone understands how this space works.
You do not need to have it figured out. You just need to come.
Our values:
We believe healing happens most deeply in spaces where people feel seen, respected, and safe to exist fully as themselves.
Our retreats are intentionally anti-racist, inclusive, justice-oriented, and affirming of LGBTQIA+ and gender-diverse identities. We ask all participants to arrive with a commitment to respect, curiosity, accountability, and collective care.
This retreat is designed for people who value:
Anti-racism and cultural humility
Diversity, equity, and inclusion
LGBTQIA+ inclusion and gender affirmation
Respect for differing lived experiences
Community care and personal accountability
You do not need to have already done this work. You just need to be willing to learn, stay curious, and show up accountable when it matters.
This retreat is NOT for you if:
You are not willing to engage with conversations about race, identity, or difference if they come up in the group
You are looking for a space that avoids these topics rather than holds them with care
You are not able to commit to treating every participant, regardless of race, gender identity, sexual orientation, body type, or background, with basic dignity and respect
FAQ
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To be Courageously Playful means embracing the freedom to let go of control, perfectionism, and the fear of judgment in order to reconnect with your authentic, joyful self.
It takes courage to step outside of the societal and internal pressures to always achieve, succeed, and appear "perfect."
Courageous playfulness is about rediscovering the joy of being present, allowing yourself to make mistakes, and nurturing your inner child—the part of you that thrives on creativity, spontaneity, and fun.
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Inner child work is an approach to recognizing and healing emotional injuries and wounds that took place in early life. By using play and exploration with a ‘beginner’s mindset’ (discovering new things and viewing experiences with a fresh perspective), you can reparent your inner child and heal old wounds. We believe that once you learn to heal your inner child, you can reconnect to your divine feminine and become your truest self.
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NOPE, our wellness retreats are NOT therapy and they are not a substitute for mental health counseling or any other healthcare service.
Our wellness retreats operate under a support model. When we work together in this way, we will be supporting you towards your specific and self-identified goals for wellbeing or self-improvement.
It’s important to note, that while we are also licensed therapists, our wellness retreats are NOT mental health counseling, nor are they considered a healthcare service, and should NOT be used as a substitute for any healthcare service.
If you require mental health support or any healthcare service, we will provide you with referrals for a healthcare provider.
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No. Everything is beginner-friendly and invitational. No yoga or art experience is required. All of the practices offered on this retreat will be accessible for all bodies and all skill levels.
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We completely understand how intimidating it can be to travel alone to a foreign country as a woman. We want everyone to feel safe and comfortable, so we have built all of our retreats to be very hands-on. We pick everyone up directly from the airport so you do not have to find your way to the villa on your own. We help ease anxiety by helping arrange everything beforehand, from packing lists to clear instructions on flight times to even scheduling calls with those who may need a bit more assurance. We plan to hold your hand every step of the way.
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We have been so very lucky to have had incredible women attend our retreats. The women have come from all walks of life and all age groups, but have formed very deep and long lasting relationships. We believe this is because we all come together with the same purpose. We all want to heal and grow and experience transformation. With this being the guiding force leading women to our retreats, we find that everyone can connect, no matter their background.
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Please bring a reusable water bottle, sunscreen, swimsuit, and clothes you feel comfortable moving in.
Yoga mats will be provided. However, you may prefer to bring your own.