Everything You Always Wanted To Know
Joshua Smith
Founder and Editor at Cruising Freedom
This is the definitive guide on Sailing Doodles for 2024.
Over the last 21 months, I have personally watched 44 hours worth of Sailing Doodles episodes as one of their biggest fans.
You could say that I’m a bit obsessed with Booby’s channel like you!
So I’m going to share with you:
➔ How Bobby afforded his boat
➔ How he makes his money today
➔ What boat he has and its upgrades
➔ Who all the beautiful women are (and how does he find them?!)
➔ How you can start crossing oceans
Before we start though, a quick introduction from me…
The Cruising Freedom Author
Ahoy, Matey! I’m Joshua from Australia.
I’ve built the perfect business to sail the world.
A business model which can allow me to:
➜ Own a catamaran debt-free
➜ Go for weeks without WIFI
➜ Create semi-passive income
➜ Inspire others to dream big
But more on that later… 🙂
Sailing Doodles FAQs (2024)
Boat Name
S/V Doodles and S/V Nauti Dogs
Crew Members
Bobby White (age 42) from Dallas, TX
Is it just me…or does Bobby look like Zach Galifianakis from The Hangover?
Taylor Francis (age 30) was previously on Doodles and was once featured on SV Delos. She recently bought her own yacht which is a 1994 Catalina Morgan 38 called Mary M, with plans to sail to Mexico, so it’s unlikely she will return.
Bobby and Taylor from Sailing Doodles were never a couple. They remained as friends only, though may have had an off-camera relationship.
Laura (LaLa Libra) was on board as Bobby’s partner but after the breakup, she left and eventually married. She is now a mom with two girls of her own with her full name now being Laura Peters, while she used the name Laura Libra on Sailing Doodles.
I was able to find full names of ex-crew members including Megan Finley and Amanda Wojtas. Each was featured in past episodes yet none of which were married to Bobby, and have moved on.
Stephanie, Tess and Geraldine are the latest girls to join the boat in Asia, with much praise of loyal fans.
The Sailing Doodles dog, Maverick, unfortunately passed away in early February, 2020 due to cancer.
The Boat
Bobby previously owned a 50-foot Beneteau yacht but no longer sails. Instead, he owns a 1997 Hatteras 60 Motoryacht which he cruises on.
In Greece, he’s sailing on a different yacht. This is a 2021 Beneteau Oceanis 62 yacht that he’s sailing on for 2 weeks. Yes, he rented this boat.
Upgrades
Bobby has upgraded his electronics, gained a new dinghy and installed new solar panels.
However, his channel doesn’t focus on renovations. Instead, he choses to focus on the near-naked women featured as guests. And the dogs.
Location
Sailing Doodles are currently in Mexico.
Past Cruising
Bobby has sailed briefly in
➔ The United States
➔ The Bahamas
➔ The Caribbean
➔ Thailand and SE Asia
Unlike other channels, he prefers coastal cruising instead of circumnavigations.
They have recently arrived in Europe and aim to sail the Mediterranean.
Affording It
Bobby had some cashed saved up before buying his first sail boat for just $24,000 plus an additional $4,000 in upgrades.
He has owned an additional 2 boats since through wise investments and YouTube income.
He previously worked as a commercial pilot, and typically flew guests on private jets.
Net Worth
YouTubers are becoming wealthier by the day. I estimate right now that:
Here in 2024, Sailing Doodles has a net worth of $2,700,000 US dollars.
This is based on the value of Bobby’s boat, online business and stock portfolio.
Making Loot
YouTube pays surprisingly well!
Sailing Doodles makes $7,600 per month on YouTube.
This is earned from the following sources:
➔ Monthly Patreon subscriptions
➔ Ad-hoc donations via PayPal
➔ Various brand sponsorships such as Butcherbox and Babbel
➔ YouTube ads on their channel
➔ Paid crew members who join in the journey
➔ Sales of the Zero to Hero online sailing course
Collaborations
Sailing Doodles had previously featured Taylor’s Travels which was very favouable to the audience.
Laura (LaLa Libra) has also been on board for an extended time but Laura’s last name is unknown. Her name ‘Laura’ may be a pseudonym as many OnlyFans creators don’t use their real name.
MJ Sailing were also featured briefly in one episode.
Back in May 2022, they finally met up with S/V Delos!
Big Moments
The biggest moments in Sailing Doodles history are:
➔ Crashing his boats on the rocks
➔ Being boarded by the coastguard
➔ Getting kicked off an island
➔ And of course, many beautiful women on board
Sadly, Bobby lost his dad recently (R.I.P.) although his mum is still alive and has been featured in some episodes.
Future Plans
Sailing Doodles aims to continue cruising in the same grounds with more women on board.
He’s already back in the Carribean and editing his older videos ready for YouTube and Patreon.
Key Takeaways
While I’m not the biggest fan of Bobby’s approach, it’s clear that the clickbait (beautiful women in thumbnails) works to generate millions of views to his YouTube channel.
Similarly, there are thousands of searches on Google each month for nude/uncensored photos of Laura and Megan by middle-aged men late at night.
He remains largely unchallenged with his ‘Sailing Boobies’ approach, providing an opportunity for similar content creators needing more views.
It’s also evident that we don’t need to do a circumnavigation to have an epic time on the water.
Conclusion
Bobby from Sailing Doodles suffered a near-death experience and used that time to re-evaluate his life choices. From there, he started sailing and never looked back simply using the resources he had.
So instead of waiting for your own health-scare, perhaps now is the time to build your own freedom-based opportunity to go cruising.
Like that old saying goes “Build your water well before you need a drink”. 🙂
Create Your Own Cruising Freedom
Hey! 😃 it’s Joshua again…
I’ve been very inspired by Doodles and their travels…
Some say I’m obsessed, but sailing the world is my childhood dream.
They’re living the dream, but that dream isn’t actually that far away.
I mentioned earlier about discovering the #1 cruising business model.
With this exciting opportunity, I’ll be able to:
➜ Generate a sustainable full-time income through learning basic skills
➜ Fund the purchase of my first sailing catamaran without any loans
➜ Do it without selling to friends and family (I found a better solution!)
➜ Share my lifetime passion for sailing, cruising and global adventures
Keen to discover more? Jump on the free training right now. 👨🏻💻
(I share more about it on the next page…🙂)
