Luxury Cruises. Tailored Journeys. Unforgettable Memories.
Based in Oakville, Ontario, Smooth Sailings Canada is a full-service luxury travel agency specializing in cruises, custom itineraries, group and family travel, and milestone celebrations. Whether you're dreaming of an ocean voyage, a cultural expedition, or an unforgettable getaway, we design seamless, enriching travel experiences tailored just for you.
I live for travel—and for helping others experience the world in ways that are meaningful, luxurious, and unforgettable. With over 75 cruises and countless global adventures behind me, along with years of experience escorting groups and planning tailored vacations, I specialize in creating seamless, personalized journeys for every type of traveler.
From ocean voyages and river cruises, to sun-soaked escapes, bucket list expeditions, and custom itineraries across the globe, I craft travel experiences that match your dreams, preferences, and travel style.
Whether you're planning a romantic getaway, a milestone celebration, a family vacation, or an immersive cultural journey, I’ll guide you every step of the way—from the first idea to the final detail.
Travel is about more than the destination—it’s about the moments that stay with you forever. I also plan:
Milestone celebrations
Multi-generational family getaways
Bucket list experiences
Global adventures and expeditions
✨ Enhance your journey with pre- or post-trip extensions for a more immersive and enriching experience.
September: Oceania’s Allura – 4-night sailing from New York City
October: Tauck’s Savoring France – 10 days on the Rhône River, starting in Paris
As a proud Virtuoso member, I offer exclusive access to benefits you won’t find elsewhere:
VIP perks: complimentary upgrades, early check-ins, late check-outs, cruise and hotel credits
Curated experiences: private events, luxury suites, and exclusive shore excursions
Personalized service that transforms a trip into a once-in-a-lifetime experience
We are TICO-certified, giving you peace of mind every step of the way. From planning to departure, we provide:
Expert guidance
Personalized service
Flawless execution
You can trust us to handle every detail—so you can focus on making memories.
Whether it’s a luxury expedition, a celebratory cruise, or a family journey across the globe, I’ll create an experience that exceeds your expectations.
✨ Follow along for travel inspiration:
Instagram: @smoothsailingscanada
Facebook: Sandra Keeso-Hall
Your extraordinary journey starts here.
What’s on your list? Let’s plan it.