September 23-25, 2025

Whispering springs in Grafton, Ontario

This isn’t your average retreat

Waypoint is a retreat for entrepeneurs, creators, and dreamers who are ready to stop spinning their wheels and start making real progress. Whether you are building a business, working on a creative project, or chasing down a bold idea, this retreat gives you the time, space, and support to figure out your next step and actually make it happen.

We will gather at Whispering Springs, a luxury glamping spot in Grafton, Ontario (only 90 mins east of Toronto). Think cozy tents, plush bedding, forest trails, and cedar barrel saunas. It is rustic in all the right ways and wildly comfortable—the perfect backdrop for slowing down and tuning back in to what you really want.

You will head home feeling recharged, focused, and ready to bring your vision to life.

Campfires, cold plunges, cedar saunas, and conversations that go way deeper than small talk. Private tents, incredible food, and the kind of people who actually get what it is like to build something.

Curious?

Autopilot Off. Intention On.

Over three days at Whispering Springs, you will step away from the daily grind and into our Intentional Living Framework: Pause. Prioritize. Pursue.

This retreat is designed for entrepreneurs, creators, and dreamers who are ready to stop spinning their wheels and start making meaningful progress. Whether you are building a business, launching a creative project, or nurturing a bold idea, Waypoint gives you the space and support to get clear on what matters and take your next step with confidence.

We chose weekdays on purpose. Your vision and well-being should not get the leftovers. Prioritizing yourself during the workweek is a bold act of self-respect, and we think you are worth it.

With a balance of guided programming, intentional downtime, and optional activities, you will experience real clarity, meaningful connection, and a fresh sense of direction, all in a beautiful natural setting with your own private accommodations.

Waypoint might be exactly what you didn’t know you needed.

Who You Will Meet THERE

Expect a small, supportive group of people who are in the arena with you:

  • Entrepreneurs building bold, purpose-driven ventures
     

  • Professionals with a business or creative idea they can't stop thinking about
     

  • Side hustlers bringing a passion project to life for purpose, joy, or extra income
     

  • Creatives and visionaries looking for clarity, connection, and momentum

Whether you have already launched or are still working out your next move, you will be in good company at Waypoint. 

Locally Sourced, Lovingly ServeD.

All meals and snacks are included. You’ll be nourished by Hawley Crescent Catering, a Feast-On™ certified culinary team serving flexitarian, locally-sourced meals that taste as good as they feel.

Meet Your Hosts

We are Whitney and Greg Boyd, a husband and wife team with a blended family, parents of four, and co-founders of Vienna Waits, a company on a mission to help one million people live with more intention.

After decades climbing the ranks in the tech world (Greg as a tech executive, Whitney in enterprise sales), we both hit major life crossroads. Through grief, reinvention, resilience, and love, we found each other and a shared belief that life is way too short to live on autopilot.

We are also entrepreneurs, building a business from the ground up. We know firsthand how exciting, overwhelming, and isolating the journey can feel. We are lucky because we have each other to bounce ideas off, to brainstorm with, and to keep each other accountable. But we know that not everyone has that kind of built-in support. That is a big part of why Waypoint exists.

We have always felt most at home in nature. There is just something about the quiet, the open space, and the grounding energy. Hosting a retreat has been a longtime dream of Whitney’s, bringing together amazing people in a beautiful setting to connect, reflect, and be inspired by each other.

Through Vienna Waits and our UNBLOCK Yourself program and podcast, we help people pause, prioritize, and pursue what truly matters with honest content, real accountability, and deep community. Waypoint is a natural extension of that.

This retreat is not about fixing you. It is about making space for you. Space to think, breathe, and reconnect with who you are and where you are headed. We are not gurus. We are real people who love deep conversations, crackling campfires, and helping others find clarity and courage to live a little more intentionally.

We hope you will join us around the fire in September.

“Whitney and Greg are two of the most authentic people I’ve ever met. They don’t pretend to have it all figured out and that’s exactly what makes them so powerful as facilitators and humans. They create spaces that feel safe, thoughtful, and real. You immediately feel like you can exhale, be yourself, and go deeper than surface-level. They are never ahead of you but walking right beside you. That’s their magic."

- Lindsay, Kitchener, Ontario

Not quite ready to book, but curious to learn more?

We’d love to connect. Fill out the form below and we’ll be in touch to answer any questions, talk details, or simply chat about whether Waypoint is the right fit for you.

The trouble is, you think you have time.

—Buddha