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Delivery Day… But My Boat Still Isn’t Ready 😬
18:56
Delivery Day… But My Boat Still Isn’t Ready 😬
200.3K views2 weeks ago
YouTubeSailing Doodles
Wasn’t Supposed to Be This Rough... Solo to Newport, RI
18:01
Wasn’t Supposed to Be This Rough... Solo to Newport, RI
78.9K views5 months ago
YouTubeSailing Doodles
Solo Sailing to the Bahamas & Crashing a Wahoo Fishing Tournament! 🌊🎣🏝️
15:06
Solo Sailing to the Bahamas & Crashing a Wahoo Fishing Tourna…
128.2K viewsMar 9, 2025
YouTubeSailing Doodles
My $1.5M Catamaran STILL Isn’t Done…
24:05
My $1.5M Catamaran STILL Isn’t Done…
148.7K views2 weeks ago
YouTubeSailing Doodles
The Dark Truth About Sailing Doodles No One Talks About
9:19
The Dark Truth About Sailing Doodles No One Talks About
29.2K views3 months ago
YouTubeVIREAL
It's finally time to set sail! After some last-minute preparations and provisioning in Fort Pierce, Florida, I cast off the dock and embark on a 15-hour solo overnight sail across the Gulf Stream to the Bahamas. The journey to Walker’s Cay was an absolute dream, with great conditions and an incredible sail. But the adventure doesn’t stop there—I arrive just in time to crash a Wahoo Fishing Tournament! 🐟🔥 Join me as I explore the island, check out the tournament action, and soak in the incredib
15:06
It's finally time to set sail! After some last-minute preparations an…
64.7K views9 months ago
FacebookSailing Doodles
Sailing South for the Winter: Solo Leaving Block Island
18:40
Sailing South for the Winter: Solo Leaving Block Island
73.7K views5 months ago
YouTubeSailing Doodles
22:13
My NEW Yacht Has Arrived! Delivering It to the Annapolis Boa…
240.4K views6 months ago
YouTubeSailing Doodles
26:27
She might hate me after this!
208.6K views1 year ago
YouTubeSailing Doodles
17:54
Baby on Board! Sailing from Athens to Aegina with Miss Lone Star
215.1K views8 months ago
YouTubeSailing Doodles
22:32
ALONE on my PRIVATE ISLAND in the Bahamas! | Preparing to Sail A…
228.8K viewsMar 13, 2025
YouTubeSailing Doodles
47:55
Big Updates… New Boat, Chloe, & What’s Next
99K views4 weeks ago
YouTubeThe Sailing Doodles Podcast
20:12
Can I Sail 500 Miles Alone Around Cape Hatteras?
110.9K views8 months ago
YouTubeSailing Doodles
19:39
The Last Sail of Nauti Dogs?
117K views5 months ago
YouTubeSailing Doodles
21:40
We’re Leaving French Polynesia… What’s Next?
242.3K views3 months ago
YouTubeSailing Doodles
27:30
Hauling Out for Hurricane Season
127.4K views8 months ago
YouTubeSailing Doodles
22:00
Prepping My Classic Yacht for an Epic 3-Month Bahamas Adventure!
119K viewsMar 6, 2025
YouTubeSailing Doodles
15:39
Total Steering Failure at Sea! | Emergency Fix to Save the Boat
131K views10 months ago
YouTubeSailing Doodles
18:24
What Really Happened to Bobby White From Sailing Doodles
147.3K views4 months ago
YouTubeScreen Static
34:31
The Insurance Saga Is Finally Over… Here’s What I Can Say
112.3K views4 months ago
YouTubeThe Sailing Doodles Podcast
10:29
Organized Chaos: 100 Boats Depart the Annapolis Boat Show!
82.6K views6 months ago
YouTubeSailing Doodles
23:30
Why Most Sailing YouTube Channels Fail After 2 Years (And …
23.1K views2 months ago
YouTubeThe Sailing Doodles Podcast
23:15
Everything You Think About Sailing Is Wrong
55.2K views4 months ago
YouTubeThe Sailing Doodles Podcast
17:09
Giving Away My Sailboat to One of You!
68.6K views6 months ago
YouTubeSailing Doodles
18:58
Lauryn Returns To The Crew For An Epic Boat Adventure!
315.9K views7 months ago
YouTubeSailing Doodles
9:03
We're Splitting Up (not click bait)
319.6K viewsFeb 23, 2025
YouTubeSailing Doodles
12:54
She Needs First Aid! - S6:E37
331.5K viewsMay 26, 2021
YouTubeSailing Doodles
13:23
Toga Party in Greece! Sailing, BBQ, and Plate Breaking
131.8K views7 months ago
YouTubeSailing Doodles
17:45
Stranded at Cat Island! Engine Troubles Before a Perfect Sail to P…
193.5K views11 months ago
YouTubeSailing Doodles
10:39
Sailing Solo Through Calm Bahamas Waters at Sunrise
112.6K viewsMar 16, 2025
YouTubeSailing Doodles
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