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.
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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.
Travel is also about perspective—literally. I see the world through my lens, capturing fleeting moments that tell stories words can’t always express. Photography is how I slow down, tune in, and preserve the beauty of the in-between. It’s how I invite others to not just see where I’ve been but to feel it—frame by frame.
Whether leading a group trip to Bermuda, designing a custom cruise itinerary, capturing photos that tell untold stories, or speaking on stages about midlife freedom, I show up with heart, humour, and a deep belief that adventure has no expiration date.
Some days, I travel solo. Other days, I’m wrapped in sea spray and sparkles, camera in one hand, caption in the other.
Canadian luxury travel content creator, cruise expert, author, & Founder of Sherry On Shore
I help women 50+ rediscover their sense of wonder through bespoke travel design, solo travel inspiration, and immersive storytelling beyond the itinerary.
My feet have touched the ground on all seven continents—91 countries and even the ice of Antarctica—but the real transformation has been internal. After nearly 15 years working onboard cruise ships and in Bermuda’s tourism industry, I’ve learned that it’s not just about checking off destinations. It’s about noticing subtle cultural differences, savoring unexpected moments, and embracing change with open arms (and often sandy feet).
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 has appeared on IMDb, NHL.com, Unreserved, and digital publications focused on travel, transformation, and women living boldly. I was recently featured in The Kingsway Magazine. I've also earned a designation in Culinary Tourism because food is one of the most delicious ways to understand a culture.
meet Sherry Mckeown
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What makes Sherry On Shore different?
01. Curated Travel & Itinerary Design
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.
Extraordinary trips. Unforgettable connections.
From girlfriends’ getaways and milestone celebrations to corporate retreats and curated solo traveler groups, I create group experiences that blend ease, adventure, and meaningful connection. I take care of the logistics, bookings, and thoughtful touches, so all you need to do is show up and make memories.
Storytelling through travel, photography, and adventure.
Through immersive storytelling, destination-focused photography, and authentic content, I bring travel experiences to life. As a trusted voice for women 50+, I collaborate with destinations, tourism boards, and luxury travel brands to create content that inspires connection, confidence, and curiosity.
02. Group Travel Planning Made Easy
03. Luxury Travel Content Creation with an Influencer Edge
Mission
At Sherry On Shore, I design transformative travel experiences that go beyond the itinerary—blending intentional planning, insider expertise, and immersive storytelling to create journeys that inspire, empower, and endure. With a special focus on women 50+ embracing solo travel, I help travelers explore the world with confidence, ease, and joy—proving that adventure has no age limit and that every journey should feel as unforgettable as the destination.
Vision
I believe travel should be more than just checking destinations off a list—it should be about connection, adventure, and experiences that stay with you long after you return home. I aim to inspire and empower travelers—especially women 50+—to embrace solo travel, discover new horizons, and redefine what adventure looks like at any stage of life. I believe travel isn’t just about where you go—it’s about the freedom to explore, the stories you create, and the confidence you gain along the way.
Once a traveler, always a traveler
My biggest inspiration? My Nanny (grandmother), who always said:
"You are only too old when you are dead."
She was right. You’re never too old to explore, try something new, or say YES to adventure.
So come along with me—whether as a fellow traveler, an armchair explorer, or someone ready to finally book that dream trip. Let’s see the world, experience new flavours, and capture every moment. Because once a travel junkie… always a travel junkie.
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