Captain Rob -

Ahoy there! I’m a thrill-seeking yacht charter captain and PADI Divemaster with a whopping 15,000 nautical miles of adventure logged and counting. My recent gig as the captain of the Leopard 58, S/Y Leeway was nothing short of exhilarating. Picture this: I dove into an offseason refit like a kid in a candy store, adding a shiny new generator and a dive compressor to supercharge our vessel for unforgettable dive charters. My days are a whirlwind of crafting unique itineraries, orchestrating smooth operations, and turning every guest's vacation into a splashy success as we explore the stunning waters of the BVI and beyond.
Before taking the helm of Leeway, I had the pleasure of captaining the Lagoon 52, S/Y Ventana. From navigating the iconic New York Harbor to handling all sorts of maintenance and repairs, every day was an adventure. I even orchestrated a smooth transfer of the vessel to new owners and delivered it to Belize, setting it up for its next chapter as a charter boat. My time with Sailaway New York on the Jeanneau 50 was equally action-packed, where I balanced daysails, Coast Guard inspections, and even dabbled as chef and photographer. Every moment was an opportunity to create unforgettable memories!
My journey also includes leading luxury home construction projects as a Senior Project Manager at WoodHull Maine, where I ensured every detail was spot-on. As Captain of the Fountain Pajot 50, S/Y Oceanfront Property, I planned epic week-long charters, kept the vessel shipshape, and engaged with guests and brokers to deliver stellar sailing experiences.
With a treasure chest of certifications including USCG 100 Ton Master and PADI Divemaster, plus a degree in mechanical engineering, I mix technical savvy with a zest for adventure. Every charter is a new opportunity to make waves and craft joyful, memorable journeys for our guests. Ready to set sail? Let’s make some unforgettable memories together!

Chef Kylie -

Meet Kylie, your Chef with a zest for adventure and a flair for the culinary arts, all the way from South Africa! Kylie’s journey from the vibrant streets of Johannesburg to the high seas is a tale of unexpected twists and thrilling discoveries. After studying Fine Arts at UCT, she embarked on a “gap” year that quickly turned into an exhilarating career voyage. Her initial foray into video production with a top cruise line company was just the beginning, leading her to uncover her true passion for service and forging genuine connections with people.
What started as a brief adventure turned into years of globetrotting across more than seventy countries, where Kylie immersed herself in a world of diverse culinary experiences. Each destination added a new layer to her love for food, transforming her gap year into a lifetime of flavorful exploration.
With a heart full of wanderlust and a deep love for the ocean, Kylie decided to turn her passion into a marine career. Combining her artistic background with her culinary skills, she found the perfect canvas aboard mega yachts. Here, she creates mouthwatering dishes that blend inspiration from her travels with a deep appreciation for healthy, vibrant food. Prepare to delight in simple yet delicious fare, featuring bold and sometimes exotic flavors that will make your taste buds dance with joy!
When she’s not conjuring up culinary masterpieces, Kylie is all about balance. She dives into her other passions—yoga, scuba diving, fishing, and savoring great films. Her goal is to make each charter an unforgettable experience, where every meal and moment is crafted to perfection.
Join Kylie on a culinary journey that’s not just about food but about creating lasting memories. With her dedication to making each voyage spectacular, she’s set to turn your time on the high seas into a delightful adventure of ocean wonders and palate-pleasing delights!

Mate Stuart -

Meet Stuart, our vibrant mate aboard Sail Yacht Tryst, where he brings a perfect blend of expertise and enthusiasm to every voyage. Though Stuart's journey began far from the sea in Johannesburg, South Africa—where he spent his youth showjumping and working with horses—his passion for adventure was evident early on. From working in a local tack store to diving into marketing and digital content creation, Stuart’s career was anything but ordinary.
With a degree in marketing and business management and hands-on experience in real estate digital marketing and automotive content creation, Stuart’s skills were finely tuned for the fast-paced world of yachting. Deciding to swap land for sea, he plunged into maritime operations, gathering a treasure trove of experience from the engine room to navigating the stunning Caribbean waters.
Stuart’s dedication to excellence ensures your voyage is smooth, safe, and full of unforgettable moments. He knows the Caribbean like the back of his hand, from secret beaches to lively local spots, and he’s excited to share his insider tips with you. Known for his friendly and approachable nature, Stuart is here to make your time aboard exceptional—whether he’s helping with equipment, providing local recommendations, or just making sure you’re comfortable.
He’s also part of an incredible team alongside his sister Kylie, our talented chef, and Rob, our experienced captain. Together, they’re committed to delivering top-notch service and creating a sailing experience you’ll remember for a lifetime.
When he’s not busy ensuring everything runs smoothly, Stuart loves capturing the magic of the journey through content creation, adding a personal touch to your adventure. He’s thrilled to share his love for the sea and the Caribbean with everyone on board, making each moment truly special.
Ready for an adventure? Stuart’s got you covered!