Sandra Keeso-Hall

Welcome to Smooth Sailings Canada Luxury Cruises. Tailored Journeys. Unforgettable Memories.

If there’s one thing I live for, it’s cruising—and creating unforgettable luxury travel experiences. With over 75 cruises under my belt, including escorting numerous group sailings and owning a cruise-specialty agency, I specialize in matching travelers with the perfect cruise line and itinerary to ensure a seamless, unforgettable vacation.

I work with the world’s top luxury cruise lines including Regent Seven Seas, Ponant, Explora, Silversea, Seabourn, and Oceania, as well as premier river cruise brands like Tauck, AMA, and Uniworld. Whether you seek cultural immersion, thrilling expeditions, or family adventures, I’ll create a bespoke itinerary just for you.

Beyond cruising, I plan milestone celebrations, multi-generational family getaways, and unique global adventures, ensuring every traveler—from grandparents to grandchildren—has a journey to remember.

One of my greatest passions is helping clients plan their travel bucket lists to ensure they get the chance to discover the places that matter most to them in their lifetime.

Enhance your cruise with a pre- or post-cruise extension for a deeper, more enriching experience.

2025 Hosted Sailings

• September: Oceania’s Allura – 4-night sailing from NYC
• October: Tauck’s Savoring France – 10 days on the Rhône River, starting in Paris

About Us

Smooth Sailings Canada, based in Oakville, Ontario, is a full-service luxury travel agency specializing in ocean and river cruises, custom itineraries, and sun vacations.

The Virtuoso Advantage

As a Virtuoso member, I offer exclusive benefits and access you won’t find elsewhere:

• VIP amenities: upgrades, early check-ins, late check-outs, hotel and cruise credits
• Curated experiences: private events, luxury suites, exclusive shore excursions, and more
• Personalized service that turns an ordinary trip into a once-in-a-lifetime experience.

Book with Confidence

Smooth Sailings Canada is TICO-certified, providing peace of mind when booking your dream vacation. We’re committed to personalized service and expert planning, ensuring every detail is taken care of.

Let’s Plan Your Next Great Escape

Whether it’s a luxury expedition, a once-in-a-lifetime cruise, or a family celebration abroad, I’ll craft an experience that exceeds your expectations.

Follow along on Instagram @smoothsailingscanada or Facebook (Sandra Keeso-Hall) for travel inspiration.

Your extraordinary journey starts now. What's on your list? Let’s plan for it!