Space to think.
Structure to move.
Waypoint Retreat 2026 is now open for booking.
Save $150 before May 31 with code EARLYBIRD26
Limited spots available.
NOT YOUR AVERAGE RETREAT
Waypoint is a retreat for entrepreneurs, aspiring entrepreneurs, creators, and people building something that matters.
It’s a few days to step away from the noise, get clear on what’s next, and actually move forward. You’ll have space to think, just enough structure to guide you, and a group of people who understand what it means to build something from scratch.
The retreat is held at Whispering Springs, a luxury glamping retreat in Grafton, Ontario (only 90 mins east of Toronto). You’ll stay in cozy, private accommodations surrounded by forest trails, with access to a cedar sauna and cold plunge, swimming pool and a lot more.
It’s the kind of place that helps you slow down, think clearly, and leave feeling focused and recharged.
What SOME 2025 Attendees have said…
“I would describe the value as a beautifully curated experience, container and community to go deep into your inner work that is easily shared with like-minded people. it's value is compounded by the shared experience and support from all the people who attend. It's got a bit of everything for anyone on this personal development path (no matter what stage you find yourself in) - it is made for the deep thinkers, feelers and high lever action takers. ”
— Lacey H. “As a young adult who often feels the pressure to keep moving and stay productive, the idea of pausing, prioritizing, and pursuing helped me shift my mindset. It reminded me to let go of what I “should” be doing and instead see it as something I “get to” do. Whitney and Greg’s attention to detail made the experience feel intentional and welcoming. Thank you again for such a memorable experience.”
— Will G. “It was incredible to meet and connect with new, interesting people! Surround yourself with interesting people and interesting things happen :) The resort itself was fantastic and I loved all of the activities that Greg and Whitney planned. The ice breaker exercise was fun and inspiring, it was a thrill to be around like-minded people who are focused on growing and living with intention.”
— Dana S.“The value of this retreat is that it gives you exactly what you didn't know you needed. But once it was in front of you, there was no way this wasn't what you were looking for! It was nourishing for the mind, body and spirit.”
— Sarah N. “Waypoint offered a rare and valuable pause, a chance to step outside the day-to-day noise and reflect on where I am and where I want to go, both personally and professionally. The space was intentional, the people were inspiring, and the conversations were deeply grounding. I left feeling more aligned, re-energized, and committed to showing up as the best version of myself.”
— Oluseun O. “Greg and Whitney did an excellent job of expertly and thoughtfully building the program and workflow, balanced nicely with times for a group discussion, individual focused, work, plenty of valuable formal, and informal interaction time in the beautiful natural setting. The guidebook prompts are thought provoking and challenging but doable, and the key follow-up activities, check-ins and support are really going to ensure that the work and progress continues towards achieving the goals I’ve set for myself.”
— Kevin M. “I rarely give anything 5 stars. But the location and food really was perfect. I hope to be at Waypoint every time you do it, and I hope you never have it anywhere else.”
— Bob M.“The retreat exceeded my expectations in so many ways.
I didn't have a planned idea of what it would be like, but wow, it surpassed anything I thought of. The food was incredible, my tent was out of this world, and the days were planned with a perfect mix of free time and planned time. What stood out to me was every little detail that had been thought of, as well as little moments that brought me back to why I was there to begin with - to find inner peace, inner purpose, and hone in on my goals over the next 12 months.”
— Lindsay L.“Waypoint retreat is transformational. I left feeling incredibly refreshed, confident, and eagerly excited to fulfill my greatest desires with the actionable conviction I felt through the attending retreat. There is not enough gratitude to share to Whitney and Greg for this experience. I left wanting more time and connection with the incredible Waypoint family that we formed.”
— Brie P. Autopilot Off. Intention On.
Over three days at Whispering Springs, you’ll 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’re 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 at Waypoint
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 (very) 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.
As 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 Retreat exists.
We have always felt most at home in nature. There’s 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 our UNBLOCK Yourself program, podcast, corporate work and content 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 isn’t about fixing you. It’s about making space for you. Space to think, breathe, and reconnect with who you are and where you are headed. We’re not gurus. We’re just 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.
“Waypoint curated the environment I needed to step into possibility. From food, surroundings, and fellow participants, Greg and Whitney crafted an experience and container for amazing things to happen.”
-Sarah N. Waypoint 2025 Attendee
Not sure if Waypoint is right for you?
Reach out. We’d love to chat and help you figure it out.
The trouble is, you think you have time.
—Buddha