Cheryl Guilfoyle

I’ve always been drawn to getting off the beaten path, whether that’s time on the water, up in the mountains, or exploring quieter, lesser-known places where travel still feels authentic. I love planning the next adventure for family and friends, often chasing experiences that sit far from the crowds and feel truly rooted in place.

As a mom of three boys, travel has taught me to plan thoughtfully and with care. Trips are rarely one-size-fits-all, and finding the right balance between adventure and downtime, shared experiences and individual interests, and very real budgets takes time and intention. I’m drawn to travel that includes movement and discovery, from hiking mountain trails and skiing to sailing and exploring new corners of the world, paired with thoughtfully designed, smaller boutique properties that feel connected to their surroundings.

At the heart of it, I love exploring the world with family and friends.

Cheryl lives in Toronto, Canada