Who is Bobby White (aka “Sailing Doodles”)?
Bobby was living the corporate dream as a pilot. In his thirties, he’d traveled the world by plane and done well for himself financially in the process. He was working as a private pilot for a wealthy family in Texas before his stroke.
Bobby suffered from a hemorrhagic stroke, which left him unable to pilot anymore. The first few weeks of recovery after a stroke are crucial, and Bobby ended up having to teach himself how to read again.
Once piloting was no longer an option, Bobby tried his hand at different careers, but nothing stuck. At that time, sailing blogs like Sailing LaVagabonde and SV Delos were doing very well. Bobby decided he’d try his hand at the vlog life.
In a deciding sweep, he sold everything he owned and started filming. He titled his series Sailing Doodles after his two labradoodle dogs, Maverick and Goose.
Setting Out on Ruff Seas
Of course, there’s no sailing vlog without a sailboat. So, Bobby bought a 37’ C&C that was built in 1984. Like any older boat, it needed some TLC. But $4,000 of updates later, Ruff Seas was ready to sail.
Bobby and his friend Megan started their venture in Houston, TX, and traced along the coast to the Florida Keys. As they sailed to the Bahamas, they realized that Ruff Seas wasn’t the best boat for sailing the Caribbean. It didn’t hold enough water or fuel for longer voyages, and its deep draft made sailing shallower waters tricky.
But, Ruff Seas was never intended to be permanent. Bobby planned to sail her for a year, get comfortable, and then sell her to pursue a crew position on a bigger yacht.
Unexpected Changes
Things were going to plan for Sailing Doodles. Bobby got a job sailing another boat from Saint Maarten to Florida. Before he left, Ruff Seas was under contract to sell.
During that same time, a hurricane-ravaged Puerto Rico where Ruff Seas was docked. Unfortunately, Ruff Seas was caught in the path of the hurricane and suffered a broken mast and damaged hull.
Bobby Ended up giving away Ruff Seas and starting from ground zero again. The Sailing Doodles vlog had accumulated quite a few followers by that point, and Bobby had enough income from the vlog to support himself for a little while. Though, he didn’t have enough to purchase another sailboat.
Making the Best Out of a Bad Situation...Again
So, he thought he’d try to turn Sailing Doodles into a travel vlog, and he headed to Thailand. If not for a successful travel vlog, then at least as a last hoorah before going back to real life.
While in Thailand, an opportunity appeared for Bobby to interview Ron Patson, the owner of Gulf Charters. Along with the interview, Sailing Doodles toured their fleet and got to know the operation well.
As Ron and Bobby got to know each other, an opportunity arose. One of Ron’s sailboats had been in Vancouver for three years, and he needed someone to sail it back to Thailand. The sailboat was a 50’ Beneteau named White Squall.
To sweeten the deal, Ron told Bobby that as long as he brought White Squall back to the fleet in Thailand by August 2018, then the sailboat was his. Of course, it was an opportunity that couldn’t be passed up.
Sailing White Squall
White Squall received a major retrofit, and it was ready for a long ocean crossing. Bobby’s then-girlfriend, Laura, decided to join him on the voyage for two months. She worked as a traveling nurse, and she was planning on getting a nursing job in Florida.
So Bobby left Vancouver and picked up Laura in Washington so they could begin their trip south along the west coast. But soon Laura’s two-month plan turned into staying with Sailing Doodles for longer. She’d fallen in love with the sailing life.
Bringing Followers Onboard
Sailing Doodles’ YouTube channel provided some revenue, but it takes more than you’d imagine to fund a 50’ sailboat’s voyage and to create enough content for a YouTube series.
So, like many other YouTube channels, they offered followers the chance to come on board with them. They rented out cabins on White Squall for people to spend a week or a weekend onboard. Meals were included. All they had to do was take some night watch shifts and help with regular chores.
This extra source of income helped to pay for marina fees, fuel, and maintenance. They found that once they reached Mexico, interest in their channel had picked up. Not only were they renting out cabins on White Squall to their subscribers, but they were also scheduling meet and greets along the way.
They had a deadline though. They had to get back to Thailand and return the boat by August 2018. Gulf Charters was helpful in this. Ron Patson of Gulf Charters helped them to chart their course so they’d make it in time while still getting to all the views.
They sailed White Squall into port with little time to spare, and they sailed home to the United States a few days later.
More Bad Luck?
Once getting back home, Sailing Doodles was quick to get back on the water. Bobby purchased another sailboat and named it Nauti Dogs. This new-to-them sailboat was a CT 56’ and stunning.
Sailing Doodles purchased the CT 56 in 2019, and sailed it to the Bahamas for the sailing season. Only for more disaster to strike a year later. On a solo sail, Nauti Dog’s transmission blew up, causing a fire on board.
After trying to put it out, Bobby ended up having to call the Coast Guard and get rescued. The fire left Nauti Dog in a bad state, burnt and sinking. After inspection, they found that the boat had sustained 100,000 dollars in damage. Insurance refused to pay for the repairs.
So, once again Sailing Doodles found themselves with no sailboat and a sailing vlog waiting for content.
What Sailing Doodles is Doing Now
Sailing Doodles has six seasons on YouTube. You’ll find a new video every week on their channel. At the time of writing this article, they’re on episode 17 of season 6. That episode shows Bobby and his girlfriend in Belize. Since Nauti Dog suffered such a tragic fire, they’ve been chartering boats in the Caribbean.
Despite the pandemic, Sailing Doodles continues to travel the world and stay socially distanced at the same time. Thankfully, sailing is a socially distanced activity, to begin with.
Though chaos is a sailor's life sometimes, Sailing Doodles is a great example of how to deal with unexpected circumstances and always make the best out of any situation.
Other Sailing Vlogs to Follow
Sailing Doodles is one very popular sailing vlog that is still active today. But, they weren’t the original sailing vlog, and they’re not the only ones. If you need more of a sailing fix in between Sailing Doodles episodes, then you’re in luck. There’s a ton of sailing content out there if you know what you’re looking for.
Sailing La Vagabonde
Riley and Elena have been sailing together for years now. They started on a monohull but have since been elevated to a catamaran. They moved to a bigger space just in time too, because now they have their son, Lenny, sailing along with them.
Sailing LaVagabonde is a family-friendly, informative, and entertaining sailing vlog on YouTube. Like Sailing Doodles, they support their sailing adventures through their online content. They’re reliant on viewers and Patreon supporters to continue their sailing dreams.
SV Delos
If you’re looking for a lot of content, then SV Delos is the YouTube series for you. They’re one of the original sailing vlogs, and they have the content to prove it. At this moment of writing, they have a total of 304 episodes documenting their sailing journey around the world.
Like Sailing Doodles and Sailing LaVagabonde, SV Delos supports their sailing adventure through YouTube profits and Patreon supporters. It’s been the same crew since the beginning, and now they’ve got a baby on board as well.
If you want to learn about different hidden sailing ports and what’s involved in owning a sailboat, following a sailing vlog is a great way to do that. Or, just live vicariously through them, and enjoy watching the ride.
