Picture this: it’s the night of November 15, 2020, and the hull of Nauti Dogs groans under 40 – knot winds near. Bobby White, the mastermind behind Sailing Doodles, and his partner jolt awake to the acrid smell of burning rubber—their boat’s transmission is on fire. As flames lick the engine room, Bobby radios the Coast Guard while Jenny grabs fire extinguishers, her hands shaking but her voice steady: “This isn’t how we imagined a new season starting.” This raw, unfiltered moment—captured in their viral video “On Fire, Sinking, Rescued by the Coast Guard”—epitomizes the essence of Sailing Doodles: adventure, resilience, and a commitment to sharing every jolt of the journey.
From Motor Yachts to Sailing Souls: The Birth of a Dream
Bobby, a former commercial pilot, and Jenny traded their land – based lives for the allure of saltwater. They made a bold purchase: a 1997 Hatteras 60 – foot motor yacht they nicknamed “The Dark Side”. “We were landlubbers with a YouTube dream,” Bobby admits. Their early videos—filled with awkward dockside collisions and overpacked cabins—struck a chord: “We wanted to show that you don’t need ‘expert’ status to chase the horizon.”
But as their love for sailing deepened, they craved the freedom of wind – powered adventures. In the early 2020s, they sold “The Dark Side” and dove into a new chapter. In October 2023, Bobby purchased a 2001 Jeanneau 37 sailboat and began test – sailing it in the Greek Islands. “Our first tack in the Aegean Sea? We gybed too late and nearly capsized,” Bobby laughs. “But that’s the magic—every mistake became a lesson we shared.”
The Journey: From Greek Islands to Florida Keys—A Patchwork of Adventures
A Mediterranean Masterclass (2023)
Their three – month voyage through the Greek Islands in the Jeanneau 37, starting from October 2023, was a symphony of cobalt coves and ancient ruins. At sunset in the Cyclades, Jenny cooked moussaka in a pitching galley while Bobby rigged a makeshift clothesline between the mast and boom. “The best part? Anchoring off Ikaria and being greeted by local fishermen who taught us to read the meltemi winds by the angle of their fishing nets,” Bobby recalls. These moments—blending cultural immersion with sailing grit—became the heartbeat of their content.
The “Nauti Dogs” Incident: A Turning Point (2020)
The transmission fire aboard their own motor yacht “Nauti Dogs” wasn’t just a crisis; it was a pivot. Stranded at sea, they filmed the entire ordeal, transforming trauma into a teachable moment. According to the video, they were waiting for a while before the rescue arrived. “We received messages from sailors worldwide who said our video saved their boats,” Bobby says. Sailing Doodles evolved from “adventure logs” to a safety – first community, with tutorials on fire drills, mayday protocols, and DIY engine maintenance.
Current Chapter: The Searay Sundancer and Beyond
Before January 2024, they welcomed a 2001 Searay Sundancer 340, christened “Doodles”, for cruising the Florida Keys and Bahamas. “She’s not a sleek racer,” Bobby explains, “but she’s our classroom—where we test solar panel installations, experiment with fuel efficiency, and host live Q&As from the flybridge.” Meanwhile, they await their Island Spirit 525e Catamaran, which is expected to be delivered in the late spring of 2024, a vessel designed for long – haul expeditions and their upcoming Arctic Circle voyage.
Sailing Doodles Academy: Where Novices Become Navigators
“Zero to Hero” in Over 6 Hours
Their Sailing Doodles Academy is a love letter to self – reliance. The membership has multiple tiers, with the starting price being approximately $8 per month. Members access “Zero to Hero: Sailing School”, a course lasting over 6 hours, covering everything from knot – tying (“The bowline is your lifeline—master it before you master the wind”) to emergency communications. “We failed forward so others don’t have to,” Bobby says, referencing their early mishaps. The academy also features their “Crew Readiness Checklist”, a resource they developed and widely promote for safer voyages.
Flotillas: Sailing as a Shared Language
In January 2024, their British Virgin Islands Flotilla invited sailors from around the world to join them in the gorgeous BVI waters. The event attracted multiple yachts and crews from various places globally. “Watching them bond over a sunset sail in Virgin Gorda—that’s when we realized we’d built more than a channel; we’d built a community.”
Beyond the Horizon: A Legacy of Connection
Sailing Doodles’s magic lies in its “warts and all” authenticity. Bobby once lost a drone (the specific value is not disclosed) in the Aegean Sea, and he laughed it off on camera. Jenny struggled with seasickness during a Bahamas crossing, and she once talked about her experience of dealing with seasickness in a video. “We’re not influencers—we’re storytellers,” Bobby insists.
Their mission? To make sailing accessible, whether through free blog guides on budgeting for long – term cruising or Instagram Reels demystifying sailboat electric systems. “The ocean doesn’t care about your resume,” Bobby adds. “It cares about your curiosity. And we’re here to stoke that fire.”
Set Sail with Sailing Doodles
Whether you’re a seasoned captain or a landlocked dreamer, Sailing Doodles offers something timeless: the belief that adventure is for everyone.
- YouTube: Sailing Doodles (Subscribe for storm stories, DIY hacks, and the upcoming launch of their catamaran.)
- Website: sailingdoodles.com (Download their free “First Sail Checklist” and join their mailing list for live boat tracking.)
- Instagram: @sailingdoodles (Follow daily updates, from sunrise sails to engine room emergencies—all with a side of humor.)
As Bobby often says, “The best part of sailing isn’t the destination; it’s the crew you share the journey with.” Join the Sailing Doodles family—your nautical adventure starts now.
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