Reality TV, Sailing Style: Best Cruising Video Series

"Don't bury your thoughts, put your vision to reality. Wake up and live!" - Bob Marley

My favorite genre of books is, no surprise, non-fiction cruising/sailing books. But I've got to be in the right frame of mind to read and actually get something out of it. If it's not quiet or I've got other tasks looming, I might as well forget about reading. My mind just won't focus under those circumstances. However, the latest wave of cruising/sailing videos is there to fill the void. Often I'll put on my headphones and let my mind drift while watching YouTube just before bed. I know in a sense this is burying my thoughts and escaping the reality of a long, cold winter, but I've accepted that in the short term.

Our addition (from a few boats & years ago) 
to YouTube's cruising annals.

Several years ago when I first started blogging (~2007), YouTube was still just an infant and there was little in the way of sailing content. Nowadays, there seems to be a new and interesting voyage being documented through YouTube every couple of months. I hope the trend continues because I enjoy watching most of them much more so than anything that's on broadcast or cable television. Sure, the production quality is often low (shaky cameras, lots of wind noise, loose or absent plots), but the characters are true reality personalities.

I'm of the mind that the only thing more boring than playing golf is watching golf on television, so I can understand how some of you might think watching sailboat cruising videos is a snoozefest. But truth be told, there's nothing more entertaining and fulfilling for me than being on the water under sail, so watching it on an iPad screen works for me too, even if the wind and spray on my skin are imagined. Based on the Patreon per-video profits and subscriber numbers for several sailing YouTubers, I'm not the only one.

In any case, here's what I've been watching since s/v Bearly-A-Wake was hauled for winter:

Wicked Salty: Wes, Kate and their dog Lola purchase an Ericson 30 and journey from the east coast of the U.S. on through a romp in the Bahamas.

SV Delos Sailing: You probably already know Delos, Brian and crew. This video series has a ton going for it. First, they're the exception to the "low production quality" rule of cruising videos. Second, the characters and crew are a hoot. Third, the videos take place in ports most of us will never sail to.

Monday Never: New faces to most of us, but not a new story - This is a young couple who quits their jobs and goes sailing through the Caribbean. They're laid back, personable and fun.

Sailing La Vagabonde: Like Delos above, Elayna and Riley are quickly become rock stars of the YouTube sailing world. They've got a big subscriber list and tons of views...which speaks to how enjoyable their videos are.

Real Cruising Life with Drake Paragon: Drake tells it like is in an informative, written-blog-to-video sort of way. His videos feel honest and give a good sense of what it's like to live and travel aboard a sailboat in various latitudes and regions.

Sailing Vessel Prism: Follow Shannon and Jon as they sail their Hans Christian 33t from California to Mexico.

s/v Catchin' Rays: Watch new sailors learn the ropes on a catamaran and take her through the Caribbean.

Untie the Lines - White Spot Pirates: Mostly solo female sailing and learning aboard a classic, starting in Panama. Nike is a real go-getter!

Know of other cruising videos we should be watching? Let me know in the comments below.


  1. Anonymous11 January

    I enjoyed watching a series on SV Teleport, covering an Australian couple's journey through the Northwest Passage over the course of two summers.

  2. Dylan Winter's is on the top of my list.

  3. Anonymous13 January

    I'd have to add Sailing Uma- they are doing a great refit including an electric motor replacing the diesel. For a different take on sailing, the Race to Win Sailing Podcast which has lots of great tips on sail trim that could still apply to cruisers.

  4. Check out if you haven't already! They've got some good youtube videos going!

  5. Hopefully will be on the list soon!


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