Your Crew
Both crew members hold BVI work permits until 10/10/2026.
Captain Jake
Captain Jake’s affable good nature, easy-going personality, and caring demeanor have earned him lifelong friends and loyal returning guests. A USCG Master Captain (100-ton) and PADI Dive Instructor, Jake brings deep experience and boundless enthusiasm to every charter aboard SV Dragonfly.
Before life at sea, he was a licensed General Contractor and Real Estate Broker in California, as well as a Master Carpenter, cabinetmaker, and boat builder, skills he put to good use volunteering in Sint Maarten after Hurricane Irma. A natural athlete and lifelong adventurer, Jake played championship rugby with the Highwaymen Rugby Club and still channels that same team spirit into his crew and guests.
Born in Pittsburgh, PA, raised near Atlanta, GA, and later moving to California, Jake jokes that his “progressive spirit mixed with southern charm” makes him a captain who can fix, build, and laugh his way through anything. He loves sharing his passion for the Caribbean, especially underwater, and believes that kindness, curiosity, and connection make the best voyages.
“We live on this boat and consider it our home. We want our guests to feel the same, to relax, to laugh, and to be part of our life for a while.”
Welcome to paradise aboard SV Dragonfly!
Chef Stef
Chef Stef doesn’t just cook, she creates experiences. Her dishes celebrate the beauty of fresh, local ingredients and the joy of gathering around a shared table. To Stef, great food is about more than flavor, it’s about connection, comfort, and celebration.
Raised on a farm in Santa Rosa, California, Stef grew up cooking alongside her Nona, parents, and siblings, learning the art of slow, heartfelt, farm-to-table meals. That passion now shines through every plate she serves on Dragonfly, from her braised beef short ribs in red-wine ragu with pimento-cheese grits to her famous Peruvian chicken with fragrant green rice and vibrant green sauce.
Beyond the galley, Stef is an expert first mate, certified dive master, and warm, intuitive hostess. Whether guiding a guest through their first dive or sharing a favorite recipe, her energy fills Dragonfly with laughter and warmth.
Come hungry, come happy, and let Chef Stef feed your soul, one unforgettable meal at a time.
Jake & Stef
Together for more than 16 years and married for 10, Jake and Stef bring an effortless partnership to every charter. They worked side-by-side in Northern California before following their shared dream to the Virgin Islands, where hospitality, kindness, and adventure now define their life aboard SV Dragonfly.
They’ve been sailing and hosting in the Caribbean for more than seven years, and the 2025/2026 season marks their seventh year bringing unforgettable luxury charters to life.
They have a blended family of three grown children—a daughter (29) in Seattle, a son (26) in Southern California, and the youngest son (23) in Northern California—and are proud grandparents to two grandsons, ages 7 and the newest addition born in May 2025. During their off-season, they travel the U.S. in their 5th-wheel RV, visiting family and friends.
When they’re not hosting guests, you’ll find them diving, visiting fellow crews, or exploring hidden coves with Parker. Their favorite saying:
“We’re happiest when we’re underwater.”
Security & Cuddle Officer Parker
Meet Parker, Dragonfly’s beloved 35-lb Portuguese Water Dog and “Security & Cuddle Officer.” At just five years old, Parker has already made more than 450 guest friends! With hair instead of fur, he’s hypoallergenic and non-shedding, the perfect onboard companion.
Boat-trained since he was 9 weeks old, Parker never goes potty on the boat. He has scheduled dinghy rides to shore each day for potty breaks and loves the adventure. He also enjoys paddle-boarding, beach walks, and, of course, supervising snacks. Ever the vigilant “lifeguard,” he keeps a close eye on guests in the water and ensures everyone stays safe and smiling. His gentle nature and joyful spirit bring comfort and laughter to all who meet him.
From Parker: “I love treats, kind people, kids of all ages, and other dogs. I hope to bring you as much happiness and comfort on charter as your pets do at home.”
Whether lounging on deck or swimming by your side, Parker embodies the heart of Dragonfly: loyal, playful, and full of love.
(Parker can be boarded upon request.)
June 2026 - Multi-Generational trip
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Captain Jake, Chef Stef and Parker, <br />
What an amazing week we had getting too know you and Parker. This is a vacation like no other. It was a week of beautiful weather, fabulous food and very zen vibe. It wasn’t rushed, chaotic or stressful. A true barefoot vacation…my feet don’t remember shoes. Entry back into real life will be a shock to our systems. <br />
Thank you for the memories and great food, but most of all sharing Parker with us. Jane & Paul <br />
<br />
Thank you for the trip of a lifetime. We had a wonderful week, you spoiled us with excellent food, care and love like if we were family. Marielena & Rafael <br />
<br />
Captain Jake, Chef Stef and Parker, <br />
I am actually sad to leave. Thank you for making a trip with both sets of in-laws seamless and relaxing! Certifying Hayes and Mason to dive will be a memory none of us will forget. On to planning our next trip with ya’ll! Much love and gratitude, Chris, Yvett, Hayes, and Mason<br />
May 2026 - Epic Vacation
Stef, Jake an Parker- <br />
Where to begin? What to say that hasn’t already been said by everyone that has the privilege and true pleasure to sail with you guys! What an epic vacation for our little family. Such warm hospitality and amazing food. The table decorations were so fun too. Small things make the greatest impact. Thank you for making my “sailing in 60” and Stephens retirement moments in our life that we will never forget. <br />
I know our kids will look back at this trip many years from now and remember it as the “best trip ever”. And in Haley’s words “Soggy” is the best bar in the world 😊 Thank you for sharing Parker with us. We are all dog people and he is the icing on the cake! This is not, "thanks and goodbye" but rather “see you soon in the Grenadines!”<br />
With true love and gratitude. Stephen and Tracey, Eric and Haley, Jesse and Hannah<br />