This is the WORST Every Year (why boat insurance sucks)


Yacht insurance is the most anxiety-riddled hassle of boat life. Get Surfshark VPN at – Enter promo code WYNNS for 83% off and 3 extra months for FREE!

❤ Join Our Crew! ❤ For exclusive content, behind the scenes & Q&A’s:
☝Full Scoop On The Blog

📷 Photo & Video Gear 📷

📱 UPDATES on Social 📱

📧EMAIL notifications, so you never miss a video🍦

🎶 MUSIC for vids.
Artist: Corey Barker
Music Sourced From Filter: 

💯FREE ways to support our productions


#BoatLife #Travel

We’re starting our 6th year as liveaboard offshore sailors. And without a doubt, yacht insurance has been the most unexpected pain in the arse!

And it’s not just us, it’s every offshore USA flagged boat owner we talk to. Yacht insurance as an American sailor abroad just kinda sucks. Especially in the South Pacific (for some odd reason). I can’t offer up any words of wisdom on how to fix this mind-bending insurance system, but we have learned a lot on how to best present ourselves and our vessel.

Of course, we are NOT experts and there is still a lot we don’t know. But, if you’re a newbie buying your first boat or a fellow sailor struggling to get offshore, bluewater, around-the-world coverage, hopefully, this information will make the process suck a little less.

Here are the biggest tips we’ve learned about getting boat insurance:


We’re Jason and Nikki Wynn. We been living #OffTheGrid and exploring the world for 10 years.
Our first six years of travel were an epic road trip around North America.
Now we’re on a #sailing voyage about the world. Did we have any previous sailing experience, of course not!
Neither of us is overly talented, smart, rich, lucky, or retired. But that doesn’t stop us from reaching far-flung destinations, having wild #adventures and managing everything that makes living aboard a moving vessel possible.
We’re two ordinary people that just so happen to live an extraordinary life.
And this is why we publish our lives on the world wide web. We share in hopes of inspiring you to find your adventure.

Timestamps if you like to Jump Around:

00:00 Sunrise & Yacht Insurance Sucks
01:50 Insurance is Cancelled & Finding New Insurance
02:47 Why We NEED Sailboat Insurance
05:30 The Worst Yacht Insurance Story
06:57 How We Search for Insurance
08:48 Insurance Year 1 as a New Sailor
09:31 Insurance Cancelled EVERY Year (US Sailboat)
10:11 Cost of Around The World Yacht Insurance
10:49 Why Yacht Insurance Cost So Much
11:39 Tips to Apply for Boat Insurance
12:39 2 BIGGEST Tips to Save Money on Insurance
14:14 Why Deal With This Hassle to Sail Around the World?
15:24 Bloopers



© Gone With the Wynns 2021

Discover more from SAILING and YACHTING

Subscribe now to keep reading and get access to the full archive.

Continue reading