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Sherry McKeown
Toronto, ON Travel Agent
Areas of expertise
Destinations:
Bermuda, Antigua & Barbuda, Cozumel, Croatia, TorontoInterests:
Cruises, Bespoke Travel, Wellness, Women's Travel, Sporting EventsSuppliers:
Norwegian Cruise Line, Virgin Voyages, EnterpriseAbout Me
Luxury Cruise & Bespoke Travel Designer
Hi, I’m Sherry — a luxury cruise expert, travel content creator, and bespoke itinerary designer with a deep love for the sea and a passport stamped on all seven continents.
I’ve been in the travel industry for over 15 years, working both on land and at sea, from sailing onboard cruise ships around the world to managing shore excursions in Bermuda, to now designing unforgettable journeys for clients who want more than just a vacation. I specialize in luxury cruises, immersive travel experiences, and curated itineraries for those who want to explore with depth, intention, and a touch of wow.
My love for travel didn’t begin in a textbook, it began with a snowstorm, a spontaneous decision, and a leap onto a cruise ship that changed my life. I walked onto that ship not knowing a thing about maritime life, and walked off years later with global stories, lifelong friends, and an unwavering belief in the power of travel to transform us. Since then, I’ve lived and worked in Bermuda, explored over 90 countries, and turned my passion for hospitality, storytelling, and connection into my life’s work. I’ve spent a full month traveling solo through Croatia and the Balkans region, places I return to again and again for its beauty, history, and seaside magic, and wandered through New Mexico’s art towns and deserts, finding joy in photography, hot air balloons, and spontaneous detours. These aren’t just trips, they’re chapters in the story that shapes how I help others travel with meaning.
As a certified travel advisor (TICO), I focus on crafting tailor-made trips for clients who crave quality and care in every detail, whether that’s a luxury Mediterranean cruise, a milestone celebration at sea, or a women’s wellness escape that nourishes mind, body, and soul. I’m an AnchorBDABermuda Ambassador and an Antigua & Barbuda Specialist, so if you’re dreaming of pink sand, turquoise water, and insider tips, you’ve come to the right place.
I take pride in offering concierge-level service and bringing a creative eye to every itinerary. I charge a travel design fee to ensure you get a personalized proposal built just for you, no cookie-cutter packages here. I blend years of industry experience with an insider’s edge on what makes a destination unforgettable. My clients value my attention to detail, honest advice, and the kind of excitement that only comes from someone who truly loves what she does.
When I’m not designing dream trips or partnering with destinations as a travel storyteller, you’ll find me behind a camera lens, sipping tea, or writing about my adventures on my platform, Sherry On Shore, where I help women 50+ embrace solo travel, celebrate their spontaneous era, and fall back in love with the world (and themselves) one journey at a time.
Travel is personal and so is the way I plan it. If you're looking for someone who sees travel not just as logistics, but as a life chapter waiting to be written, I’d love to work with you.
This isn’t just travel — it’s your story, set in motion.
Let’s turn your next trip into your best story yet.
Why Clients Love Working With Me
Clients often tell me I make travel feel effortless, exciting, and personal. I bring warmth, creativity, and insider know-how to every itinerary, and I’m known for truly listening and delivering thoughtful details that make all the difference. Whether it’s finding the perfect cruise for your style or uncovering hidden gems on shore, I design trips that feel like you. I’ve traveled to all 7 continents, worked onboard ships, and lived in Bermuda. I bring that real-world knowledge to every booking. From solo escapes to milestone celebrations, I’m here to make your next adventure unforgettable.
Areas of expertise
Destinations:
Bermuda, Antigua & Barbuda, Cozumel, Croatia, TorontoInterests:
Cruises, Bespoke Travel, Wellness, Women's Travel, Sporting EventsSuppliers:
Norwegian Cruise Line, Virgin Voyages, EnterpriseCertifications & Awards


