600 Miles Across the Most Feared Ocean on Earth
Join Jason and Nikki Wynn on an exhilarating sailing adventure from Antarctica to Argentina as they navigate the infamous Drake Passage—a body of water known for its fierce storms and unpredictable conditions. In their latest video, the couple recounts a journey that’s as daunting as it is breathtaking, filled with icebergs, whales, and the spectacular landscapes of the Frozen Continent.
After spending a month marveling at the beauty of Antarctica, the Wynn’s prepare to set sail northward aboard their yacht, S/V Icebird. However, their path is fraught with challenges, as the notoriously turbulent Drake Passage stands between them and civilization. In this gripping video, viewers will experience the wind-swept waves and deep blue waters that have inspired both fear and awe in sailors for centuries.
Throughout their journey, the Wynns engage with the themes that have driven their explorations for over a decade: curiosity, self-reliance, and the importance of human connection in remote places. Along the way, they share insights on preparing a sailboat for the harsh conditions of the Drake Passage, offering valuable tips for fellow adventurers.
With stunning cinematography and an inspirational message, this video captures the thrill of adventure while also encouraging viewers to embrace the unknown. Witness how Jason and Nikki cultivate curiosity in every experience, reminding us that sometimes, the most transformative journeys are the ones that push us out of our comfort zones.
Get ready to sail along the edge of the world and discover what lies beyond—and remember, every great journey begins with a single step (or sail).
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Video “600 Miles Across the Most Feared Ocean on Earth” was uploaded on 05/24/2026. Watch all the latest Videos by Gone with the Wynns on Gretopia




























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Holy man this is intense to watch. Seeing the swells was just holy man.
I like your style
what are your thoughts on an aero rig equipt cat?
Freakin amazing! I watched with so much envy! I do so wish I would have started boating sooner in my life. (We sold our boat after Hurricane Ian)! I would have done it all! Thanks for taking me along with you on this amazing adventure! I can’t wait for your next one.
I’m a lifelong sailor, who has 3 years ago bought our first motor yacht (Ocean Alexander 42). I’m on the West Coast of Canada, but in “protected” waters… even so I’ve had to learn that motor yachts do not fare well in any kind of beam sea (that is, without stabilization). Buddy boating with friends on their 42’ sailboat revealed what is an ideal sailing day for them is a no-go for us. We need almost flat seas. If you are going to explore high latitudes, your stabilizers will have to be up for days of constant use.
Thank you for sharing the adventure.
I'm interested to know if your new boat can cope with that kind of trip?
What a trip, such pure and basically untouched beauty. How can anyone not say that was the trip of a lifetime, incredible!
Home Run !! Absolutely Loved it !!
Have you ever read Endurance by Alfred Lansing, Shackletons incredible voyage. Outstanding! Great read!
Dreamed of sailing around Cape Horn since I was a kid. Wonderful video
Nikki, Jason; something confuses me. Lifting your index finger and pinky finger means "bullshit". What does lifting your thumb and pinky mean? Oh, by the way. You have witnessed the Grandor of The Great Spirit and this is only a sample of His work!
My salute to your adventure is a little ditty based on the song "The Mighty Quinn" sung by Manfred Mann and written by Bob Dylan.
The Mighty Wynns
*Verse 1*
Everybody grins when the Mighty Wynns
Come charging through the spray.
Icebird’s bow cuts a silver line
Where the white ghosts drift and sway.
She hums her tune in the frozen noon
As the down slope winds begin,
And the whole world cheers when the hull appears
It’s Icebird and the Mighty Wynns.
*Chorus*
Come on all into the wandering wind
Warm right up sailing with the Mighty Wynns.
Come on in let the white world begin
Your going to be rolling with the Mighty Wynns.
*Verse 2*
Penguins line the icy shore
Like a crowd that’s come to see
This red‑hulled bird with a fearless crew
Dance through a polar sea.
The rigging sings as the Icebird swings
Past a berg with a sapphire grin,
And the compass spins where adventure begins
For the bold, bold Mighty Wynns.
*Repeat Chorus*
Come on all to the wandering wind
Warm up sailing with the Mighty Wynns.
Come on in let the white world begin
Your going to be rolling with the Mighty Wynns.
*Bridge*
Through the Drake they shake but never break,
Icebird steady on her keel.
The Southern Ocean roars its truth
A test of grit and steel.
But the Wynns just laugh as the albatross
Circles wide with a knowing grin,
’Cause the storms all bow and the waves allow
A passage for the Mighty Wynns.
*Repeat Chorus*
Come on all to the wandering wind
Warm up sailing with the Mighty Wynns.
Come on in let the white world begin
Your going to be rolling with the Mighty Wynns.
Jason, keep the beard – it’s Nordic appropriate!
I've been enjoying your adventures since I stumbled across Nikki handling the RV and Smartcar alone way back in 2016 (Nikki Goes Solo). This trip/adventure is now my favorite one!! And more to come for sure!! Thanks for bringing us along!!
11:15 Scopolamine… here, it's a seasickness treatment. In a Colombian bar, it's 'Devil's Breath'.
That a group of people could coexist on a 60 foot sailing yacht on such a trip is a trip onto itself. Oh bye the way, the Antarctic is pretty chill too. Well done.
You guys truly amaze me every time but that was a beautiful experience- you are such a great teller of your life stories! Thank you as I am touched as always and inspired! Love you- Jenn NC
Wow. The Drake freakin Passage!!! I guess you had to travel to the bottom of the world to top all your other epic experiences. I am truly in awe and so grateful you've shared this with us. 🫶🏽
Thank you for all your posts. This one is by far as good as it gets!
22:21 wow
This whole Antarctica series has been outstanding, spectacular and very well done. Thank you!
Wow! Impressive!
Tour cost? $19k pp?
sounded like a lot of "code" talk for "barfing my guts out"
It blows my mind that people did that sail in wooden ships with no stabilization or good weather forecasts. I looked up how dangerous the Drake really is, and for non professionals it's about a 5% fatality rate. That's one in twenty! 😱
First time I heard about the Drake is from what in the world with Tom, did you do the ritual before and after
My disappointment is immeasurable and my day ruined. I mean, if its not bare pole sailing in life threatening 60+ knots of wind with 30 ft swells are you really even sailing the Drake? Irving Johnson is shaking his fist on the top royal spar of Peking saying "are you even really sailing?"
LOL, thats a joke people, dont take it seriously. But do check out his black and white docu of sailing the wind jammer Peking. Classic.
Thanks for sharing 😊
🌬❤️😊❄️🐧🐋👏👏👏👏👏👏👏👍👌⭐️🍪
OK Yeah …. That was AMAZING! 😳
This is the best set of episodes you’ve ever done. What a fantastic adventure!
Wow! Stunned. I have no words. Just great. You lived experiences that 99.9% of the world will never see. Thanks for taking us along for the ride!
3 hours on/6 hours off?? You have enough bodies for too change that??????
I know that your sunglasses are probably functional, but they are the ugliest sunglasses EVER!!
I know you are not a technical sailing site, but you had several days with an aerorig. You need to do a full episode interviewing the captain on the aero rig. it is a very unique system that may benefit a lot of cruisers. It has a lot of pros and cons.
Still can't believe we actually did this… and we’re so glad we got to share it with all of you!
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