Sunshine. Surf. Sisterhood. Soul.

Dare to PLAY

Okanagan, BC August 26 – 29, 2026

Seven Women  ·  One Boat  ·  All In

For the women who want a little edge, a whole lot of freedom & pure fun on the water, join us in the Okanagan Lake for 2 days of play & laughter including:

  • Private boat

  • Pro coaching

  • Curated meals

  • Luxury lakeside stay

Reserve your spot below!

Only 5 spots left!

THE DARE

The excitement, the slight edge of doing something you've never done before. Seven women on a boat together cheering each other on, knowing that they all have a challenge... a different challenge.

Maybe someone has been trying to land a trick and never has. Maybe someone has never got behind the boat and felt what it feels like to be free on that board, moving, being in your body, trying something you've never tried before.

The connected feeling of being together. Excited. Alive. In your body. Trying something new. Living a little. Laughing at our silliness. Seeing each other for who we truly are in these moments.

Pro Surf Coaching

Ashley Inloes is one of the most vibrant and beloved names in professional wake surfing. Known for her smooth style, massive trick arsenal, and infectious positive energy, she has competed at the highest levels of the sport. She placed 3rd and 2nd at the World Wakesurf Championships and earned Female Best Trick of the Year for her standout performance.

But what sets Ashley apart isn't just what she can do on the water. It's how she makes you feel when you're on it with her.

Her philosophy is simple: Falling is Learning.

And that energy, fun-first, judgment-free, stoke-level-high is exactly what she brings to every lesson, every session, every moment on the boat.

A Supra Boats sponsored athlete and Phase 5 pro, Ashley collaborated with Phase 5 to create her signature board, The Mindset, designed specifically for accessibility and progression, including women and beginners.

She has spent years coaching privately, running her popular How To series online, and working with Brave the Wave, teaching wake surfing to people with physical disabilities.

For two full days on Okanagan Lake, Ashley is yours. Whether you've never been on a board or you're ready to push your edges, she will meet you exactly where you are and take you somewhere you didn't think you could go.

Ride With Us

Whether you're ready to go all in or just want to dip your toes in, there's a spot here for you. Dare to Play was designed for women who are ready to feel something, no experience required, no performance expected. Two ways to show up, one unforgettable weekend on the water.

FULL SEND

The full experience. Three nights at a private lakefront property on Okanagan Lake, all meals with the amazing Chef Mike Wilkens, two full days on the water with Ashley Inloes, morning intention, evening integration, and the kind of connection that doesn't end when the weekend does.

With accommodation · August 26–29

LOCAL LEGEND

Same magic. But you don’t need to pack a suitcase. Full retreat experience including both days on the water, all meals during retreat hours, and everything that makes Dare to Play what it is.

Experience only,·no accommodations August 26–29

Location

Location

Location

This property is something special, tucked away from the hustle and bustle, in the kind of quiet that feels worlds away.

This place is special to me. I've spent a lot of time here over the years — swimming, laughing, connecting, and living my best life on the water. It holds something good, and I can't wait to share it with you.

The sunrises are unmatched. You'll wake up to the most beautiful views of Okanagan Lake, step outside onto the deck with your favourite morning beverage, and just breathe. The water lapping at the shore a few steps below you. The stillness. The knowing that a full day of play and sunshine is coming.

There is no feeling quite like it.

Exact location details revealed upon booking.

FEAST FIRST

Collaboration with the best in the business is what we do here.

I am beyond grateful to be able to continue to work with Chef Mike on events & retreats.

From Toronto to CIA Hyde Park to Kelowna’s culinary scene Chef Mike Wilkins has been a creative force in Kelowna for over a decade.

After spending four years training at the prestigious Culinary Institute of America in Hyde Park, New York Chef Mike has honed his style of cooking that delivers comfort, creativity, and international flair paired with classic French fundamentals.

You are in for a treat

Your Questions, Answered

  • Not even a little. Ashley's entire philosophy is built around meeting you where you are. Whether you've never stepped on a board or you've been on the water before, she will coach you at your level with zero judgment and maximum fun. Falling is Learning — and you will fall, and you will laugh, and you will get back up.

  • Everything. Accommodation at the private lakefront property, all meals from arrival through to departure. Two full days of professional wake surf coaching with Ashley Inloes, morning intention sessions, evening integration, all on-water equipment, and the kind of connection that doesn't end when the weekend does.

  • All the magic, minus the accommodation. You'll join the full retreat experience including both days on the water with Ashley, all meals during retreat hours, morning and evening sessions, and full access to everything happening that weekend. You arrange your own accommodation nearby.

  • Seven. That's it. This is intentional, small enough that every woman has a voice, large enough to create real community. There is no back row at Dare to Play.

  • Full Send with accommodation: $5166.00CAD 

    Local Legend without accommodation: $4558.00CAD Both include everything listed above for their respective tier.

  • Deposits are non-refundable but transferable to a future Dare to Play retreat. Full payment is due 30 days before the retreat. In the unlikely event the retreat is cancelled by Dare to Play, full refunds are issued.

  • Full property details including address, arrival instructions, and everything you need to know are sent to confirmed guests upon receipt of deposit. Think lakeside, morning coffee on the deck by the water & private dock and lift access.

  • Swimwear, sunscreen, a water bottle, and an open mind. A full packing list is sent to all confirmed guests closer to the retreat date.

  • Any woman, coach, or entrepreneur who has become so good at building that they've forgotten how to play. You don't need to be athletic. You don't need to be a surfer. You need to be ready to dare yourself back into aliveness and willing to fall down a few times getting there.

  • Women who are coming to network, pitch, or perform. This is not a mastermind. There are no pitch decks at Dare to Play. If you're looking for a business retreat, this isn't it. If you're looking for the version of yourself that existed before the business — you're in the right place.