Delivery Day… But My Boat Still Isn’t Ready 😬
18:56
Delivery Day… But My Boat Still Isn’t Ready 😬
261.1K views1 month ago
YouTubeSailing Doodles
My New Boat Was Damaged… 12 Days Before Launch!
14:01
My New Boat Was Damaged… 12 Days Before Launch!
151.1K views2 weeks ago
YouTubeSailing Doodles
I Found the Island I Want to Retire On in Thailand
20:36
I Found the Island I Want to Retire On in Thailand
75.5K views2 weeks ago
YouTubeSailing Doodles
Could I Actually Live Here? (Thailand Test Week 🇹🇭)
13:10
Could I Actually Live Here? (Thailand Test Week 🇹🇭)
266.3K views1 month ago
YouTubeSailing Doodles
Sailing South for the Winter: Solo Leaving Block Island
18:40
Sailing South for the Winter: Solo Leaving Block Island
73.6K views6 months ago
YouTubeSailing Doodles
My $1.5M Catamaran STILL Isn’t Done…
24:05
My $1.5M Catamaran STILL Isn’t Done…
153K views1 month ago
YouTubeSailing Doodles
My NEW Yacht Has Arrived! Delivering It to the Annapolis Boat Show
22:13
My NEW Yacht Has Arrived! Delivering It to the Annapolis Boa…
248.6K views7 months ago
YouTubeSailing Doodles
15:28
I Got Sick in Thailand… So Chloe Took Over
132.3K views1 month ago
YouTubeSailing Doodles
16:10
My Boat Isn’t Ready… So We Took This One Instead
118.7K views1 month ago
YouTubeSailing Doodles
47:55
Big Updates… New Boat, Chloe, & What’s Next
83.1K views2 months ago
YouTubeThe Sailing Doodles Podcast
7:33
Who Won My Boat?
77.3K views3 months ago
YouTubeSailing Doodles
20:12
Can I Sail 500 Miles Alone Around Cape Hatteras?
111.4K views9 months ago
YouTubeSailing Doodles
15:00
Living on a Boat in Manhattan for a Week!
60.1K views6 months ago
YouTubeSailing Doodles
27:30
Hauling Out for Hurricane Season
128.5K views9 months ago
YouTubeSailing Doodles
21:40
We’re Leaving French Polynesia… What’s Next?
248.3K views4 months ago
YouTubeSailing Doodles
16:50
Dutch vs French St. Martin: Cheap Lagoon Living… Then We LEFT
113.7K views3 months ago
YouTubeSailing Doodles
17:09
Giving Away My Sailboat to One of You!
68.8K views7 months ago
YouTubeSailing Doodles
18:58
Lauryn Returns To The Crew For An Epic Boat Adventure!
321.2K views8 months ago
YouTubeSailing Doodles
18:01
Wasn’t Supposed to Be This Rough... Solo to Newport, RI
79.7K views6 months ago
YouTubeSailing Doodles
10:29
Organized Chaos: 100 Boats Depart the Annapolis Boat Show!
82.7K views7 months ago
YouTubeSailing Doodles
13:23
Toga Party in Greece! Sailing, BBQ, and Plate Breaking
132.9K views8 months ago
YouTubeSailing Doodles
15:47
The New Boat Is Almost Done… I’m Flying to Thailand
84.5K views3 months ago
YouTubeThe Sailing Doodles Podcast
39:07
Relationships, Insurance & the New Boat - Ask Me Anything
113.2K views4 months ago
YouTubeThe Sailing Doodles Podcast
26:27
She might hate me after this!
208.6K viewsApr 20, 2025
YouTubeSailing Doodles
17:54
Baby on Board! Sailing from Athens to Aegina with Miss Lone Star
216.3K views9 months ago
YouTubeSailing Doodles
22:32
ALONE on my PRIVATE ISLAND in the Bahamas! | Preparing to Sail A…
229.8K viewsMar 13, 2025
YouTubeSailing Doodles
21:54
will i ever get it together...? | SAILING DOODLES X SAILING MI…
27.8K views8 months ago
YouTubeSailing Miss Lone Star
16:13
Engine Fails at Sea + Spinnaker Disaster! | 60 Mile Sail Gone Wrong
137.7K viewsMay 11, 2025
YouTubeSailing Doodles
16:21
Want to Sail the World? Here’s Your Chance
21.6K views6 months ago
YouTubeThe Sailing Doodles Podcast
See more videos
Static thumbnail place holder