I believe travel can be a catalyst for change, because sometimes the greatest journeys aren’t just about where we go, but who we become along the way.
Through Sherry On Shore, I aim to create a vibrant community of women who say yes to new experiences, explore the world (and themselves) with intention, and celebrate the magic of reinvention.
I’ve spent nearly 15 years working onboard cruise ships and within Bermuda’s tourism sector, with my feet touching all seven continents and 91 countries, including Antarctica. That experience has given me a deep appreciation for cultural nuance, partnership dynamics, and what truly resonates with travelers and audiences alike.
Sherry On Shore also reflects a personal chapter of reinvention. I’m passionate about creating space for women 50+ to rediscover their sense of wonder through solo travel inspiration, bespoke itineraries, and storytelling that goes beyond the itinerary. Adventure, in my world, has no expiration date.
I’m a contributing author in Unreserved, a collaborative book exploring change, identity shifts, and the courage it takes to chart a new course. My chapter reflects my own journey of reinvention and the perspective I bring to my work, both personally and professionally.
I’m a certified TICO Travel Counsellor, an AnchorBDA Bermuda expert, and the only certified Canadian instructor of the SCARED SO WHAT™ personal change model. My work and perspective have appeared on IMDb, NHL.com, Unreserved, and in publications focused on travel, transformation, and women living boldly, including a recent feature in The Kingsway Magazine. I’ve also earned a designation in Culinary Tourism, because food remains one of the most meaningful ways to understand a culture.
Canadian luxury travel content creator, cruise expert, author, and Founder of Sherry On Shore
I create thoughtful travel and lifestyle content rooted in story, place, and perspective. Through Sherry On Shore, I collaborate with founders, brands, and tourism boards who care about how destinations are experienced, remembered, and shared.
Travel, for me, has always been about more than movement. It’s about noticing the in-between moments. The conversations, the light, the quiet details that reveal the soul of a place. Photography is how I slow down and tune in. Writing is how I translate those moments into stories others can feel, not just see.
My work spans content creation, immersive storytelling, bespoke travel design, and speaking. Whether I’m capturing a destination through my lens, collaborating with a tourism board, designing a custom cruise itinerary, or speaking on stages about reinvention and freedom in midlife, I bring a grounded, human approach shaped by real experience in the travel industry.
meet Sherry Mckeown
What makes Sherry On Shore different?
01. Story-First Travel & Lifestyle Content That Actually Resonates
Custom-crafted experiences, designed just for you.
From luxury cruises to Bermuda escapes and beyond, I design personalized, stress-free travel experiences that reflect your style, pace, and vision. Whether you're planning a solo adventure, group getaway, or hosted retreat, I handle the details—so you can simply enjoy the journey.
What sets my work apart is perspective.
With nearly 15 years inside the travel and tourism industry, I understand not only how destinations are experienced, but how partnerships, campaigns, and collaborations function behind the scenes. That insight shapes how I approach every project, allowing me to bridge creative storytelling with strategic intent.
The result is content and collaboration that feels effortless on the surface, while being thoughtful, credible, and commercially sound underneath.
Sherry On Shore is also rooted in reinvention.
I create space for women 50+ to rediscover their sense of wonder through solo travel inspiration, storytelling, and experiences that go beyond the itinerary. This work is informed by my own journey of change and the belief that curiosity, adventure, and growth do not diminish with age.
Travel, when approached with intention, becomes a way to reconnect with yourself and the world around you.
02. A Rare Blend of Creative Vision and Industry Intelligence
03. Reinvention, Perspective, and the Power of Saying Yes
Travel design remains part of my world, approached selectively and with care.
From luxury cruises to Bermuda escapes and intimate group experiences, I curate journeys for those who value depth, ease, and thoughtful detail. This is not volume-based planning. It’s considered, personal, and designed to feel seamless from start to finish.
I work best with clients who want travel to feel meaningful, not rushed, and who trust the value of doing things well rather than quickly.
03. Curated Travel Design, Offered with Intention
Mission
At Sherry On Shore, I create thoughtful travel and lifestyle stories that connect people to place, perspective, and possibility. Through immersive storytelling, photography, and intentional collaboration, I work with brands, tourism boards, and individuals who believe travel is not just about where you go, but how it changes you.
At the heart of my work is a belief in reinvention at every stage of life. With a special focus on women 50+ embracing solo travel and new chapters, Sherry On Shore exists to inspire confidence, curiosity, and a sense of wonder, proving that adventure has no expiration date.
Vision
I envision a world where travel is experienced with intention, curiosity, and depth, not as a checklist, but as a way of connecting more fully to place, people, and self.
Through Sherry On Shore, I aim to inspire a more thoughtful approach to exploration, one that values story, perspective, and experiences that linger long after the journey ends. I believe travel has the power to expand confidence, invite reinvention, and open new chapters at any stage of life.
At the heart of this vision is a belief that adventure has no expiration date. Especially for women 50+, travel can become a meaningful expression of freedom, self-trust, and possibility, shaping not just where we go, but how we see ourselves and the world around us.
Once a traveler, always a traveler
My biggest inspiration has always been my Nanny, my grandmother, who loved to remind me:
“You are only too old when you are dead.”
She was right. You’re never too old to explore, to try something new, or to say yes to adventure.
So come along with me. Whether you’re a fellow traveler, an armchair explorer, or someone ready to finally book that long-dreamed-of trip, there’s room here for curiosity, flavour, and discovery.
Because once travel gets under your skin, it never really leaves you.
