
The Biggest Risk of My Life—And Why I’m Sailing Around The World.
February 28, 2025 by SailorBarry | Language: EN Play Time: 00:15:03 | SAILING YOUTUBERS

Support:
Patreon: http://www.Patreon.com/SailorBarry
PayPal: http://www.paypal.me/dustcollect
Buy Us A Beer!!: https://www.buymeacoffee.com/sailorbarry
Http://www.instagram.com/SailorBarry – Barry
Http://www.instagram.com/haillymartintattoos – Hailly
Amazon WishList!: https://www.amazon.ca/hz/wishlist/ls/2DDOVBJIOW0N0?ref_=list_d_wl_ys_list_1&filter=unpurchased&sort=default&viewType=list
Sailing around the world is a dream that has ignited the imaginations of countless adventurers throughout history. For some, it’s about the thrill of the unknown, the serenity of the open sea, or the satisfaction of charting one’s own course. For me, it was a deeply personal journey born out of a moment of reinvention and a burning desire to chase something monumental.
The Dream Begins
Ever since I was 25, I’d harbored this audacious goal. Back then, life threw me a curveball that left me truly alone in this world, devoid of family and friends. Such challenges often push us towards self-discovery and dreams we never thought were possible. Sailing around the world became that beacon for me—a chance to embrace life’s brevity and do something truly memorable.
“Life is short. I want to do something big and what’s the bigger challenge than sailing around our pale blue dot?”
I knew it was a daunting task—perilous and demanding in equal measure—but therein lay its allure. Why now? Well, if not now, then when? Time waits for no one, and at 41, I was ready to commit fully to this life-defining journey.
#sailing #sailaroundtheworls #woodenboat #woodboat #aroundtheworld #dohardthings #sailingadventure
00:00 Dream to sail around the world
00:25 Why Sail Around The World
00:33 Life Is Short, Do Something Big
00:54 Sail Around The World, now or never
01:10 Who is Sailor Barry
01:34 Meet Hailly
02:15 Meeting my friends
02:31 What If It Was That Easy
03:11 Earth and the conditions on it
04:00 the best way to experience life
05:04 massive but doable undertakings
05:33 change your ways and anything is possible
06:16 how to sail around the world!
06:24 step 1: learn how to sail
06:51 step 2: start a YouTube show
06:56 step 3: get a boat
07:10 step 4: find out what’s wrong
07:28 step 5: fix it all
07:41 step 6: assessing your sails
09:19 step 7: stowage
10:00 step 8: the rig
11:02 step 9: mechanical
11:30 step 10: electrical
11:50 step 11: haul out and survey
12:00 step 12: the tender
13:10 step 13: sea trials
13:24 step14: Depart
13:39 now the hard work begins
14:01 the beginning of phase 1: the galley. Restoration
Support:
Patreon: http://www.Patreon.com/SailorBarry
PayPal: http://www.paypal.me/dustcollect
Buy Us A Beer!!: https://www.buymeacoffee.com/sailorbarry
Http://www.instagram.com/SailorBarry - Barry
Http://www.instagram.com/haillymartintattoos - Hailly
Amazon WishList!: https://www.amazon.ca/hz/wishlist/ls/2DDOVBJIOW0N0?ref_=list_d_wl_ys_list_1&filter=unpurchased&sort=default&viewType=list
Sailing around the world is a dream that has ignited the imaginations of countless adventurers throughout history. For some, it's about the thrill of the unknown, the serenity of the open sea, or the satisfaction of charting one's own course. For me, it was a deeply personal journey born out of a moment of reinvention and a burning desire to chase something monumental.
The Dream Begins
Ever since I was 25, I'd harbored this audacious goal. Back then, life threw me a curveball that left me truly alone in this world, devoid of family and friends. Such challenges often push us towards self-discovery and dreams we never thought were possible. Sailing around the world became that beacon for me—a chance to embrace life's brevity and do something truly memorable.
"Life is short. I want to do something big and what's the bigger challenge than sailing around our pale blue dot?"
I knew it was a daunting task—perilous and demanding in equal measure—but therein lay its allure. Why now? Well, if not now, then when? Time waits for no one, and at 41, I was ready to commit fully to this life-defining journey.
#sailing #sailaroundtheworls #woodenboat #woodboat #aroundtheworld #dohardthings #sailingadventure
00:00 Dream to sail around the world
00:25 Why Sail Around The World
00:33 Life Is Short, Do Something Big
00:54 Sail Around The World, now or never
01:10 Who is Sailor Barry
01:34 Meet Hailly
02:15 Meeting my friends
02:31 What If It Was That Easy
03:11 Earth and the conditions on it
04:00 the best way to experience life
05:04 massive but doable undertakings
05:33 change your ways and anything is possible
06:16 how to sail around the world!
06:24 step 1: learn how to sail
06:51 step 2: start a YouTube show
06:56 step 3: get a boat
07:10 step 4: find out what’s wrong
07:28 step 5: fix it all
07:41 step 6: assessing your sails
09:19 step 7: stowage
10:00 step 8: the rig
11:02 step 9: mechanical
11:30 step 10: electrical
11:50 step 11: haul out and survey
12:00 step 12: the tender
13:10 step 13: sea trials
13:24 step14: Depart
13:39 now the hard work begins
14:01 the beginning of phase 1: the galley. Restoration
The Biggest Risk of My Life—And Why I’m Sailing Around The World. Locations
Note of Recognition for SailorBarry
At WeBoating.com, we profoundly acknowledge the unwavering dedication that SailorBarry and other creators invests in crafting each and every video. Their passion for delivering exceptional content shines through every frame, and it's a labor of love that deserves your attention.
We invite you to watch their captivating videos and actively engage with their content, including their social media links above. Liking, commenting, and sharing their work goes a long way in fueling their creative fire.
We're also inviting you to explore any sponsorships and partnerships highlighted in the video description of "The Biggest Risk of My Life—And Why I’m Sailing Around The World.", or directly on YouTube. By considering their offerings or purchasing services and items, you not only support SailorBarry but also the brands and collaborators they're associated with.
If you have any feedback, corrections, or additional information about SailorBarry or their videos, please use the comment form below to share your thoughts with us.
Thank you for being a part of our community and supporting the creators we cherish. Your time and support truly matter!
SailorBarry Lastest Videos

Finally Varnished! YES It Was Worth The 3 Months of Sanding The Boat!
Support: Patreon: http://www.Patreon.com/SailorBarry PayPal: http://www.paypal.me/dustcollect Buy Us A Beer!!: https://www.buymeacoffee.com/sailorbarry GoFundMe: https://gofund.me/79e54e5d Life Is Like Sailing: https://youtube.com/@UCNTcBlX5jZH9raUfr2dSb...
The Clock Is Ticking: Making This Space Livable.
Welcome to season 3 of Sailor Barry & Hailly This week we’re making huge changes down below decks, come check it out! Support: Patreon: http://www.Patreon.com/SailorBarry PayPal: http://www.paypal.me/dustcollect Buy Us A Beer!!: https://www.buymeac...
3 Months Of Sanding In A Confined Space.
Welcome to season 3 of Sailor Barry & Hailly This week we’re making huge changes down below decks, come check it out! Support: Patreon: http://www.Patreon.com/SailorBarry PayPal: http://www.paypal.me/dustcollect Buy Us A Beer!!: https://www.buymeac...
Restoring A Wooden Boat: So Close Yet So Far.
Welcome to season 3 of Sailor Barry & Hailly This week we’re making huge changes down below decks, come check it out! Support: Patreon: http://www.Patreon.com/SailorBarry PayPal: http://www.paypal.me/dustcollect Buy Us A Beer!!: https://www.buymeac...
Painting Over Wood, No Turning Back. Making Huge Progress On Our Boat Interior Renovation.
Welcome to season 3 of Sailor Barry & Hailly This week we’re making huge changes down below decks, come check it out! Support: Patreon: http://www.Patreon.com/SailorBarry PayPal: http://www.paypal.me/dustcollect Buy Us A Beer!!: https://www.buymeac...