Sailing With Phoenix | Oliver – Page 4

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No better feeling than fixing the wrong thing lol
Sailing With Phoenix | Oliver
I’ve picked the new captain for Phoenix.
Sailing With Phoenix | Oliver
My Final Sail Aboard Phoenix (and Losing the Drone)
Sailing With Phoenix | Oliver

My Final Sail Aboard Phoenix (and Losing the Drone)

Well, my last voyage with her was bound to happen eventually. I’m glad we ended things on such a high note. The sailing conditions were perfect, magical, even (aside from losing the drone 😅). The Molokai sea cliffs at sunset were absolutely breathtaking, and she brought us home safely one last time....
Change of plans people. We’re going to the moon.
Sailing With Phoenix | Oliver
There will be ups. There will be downs. Through it I will become wiser. 5 months to get it done.
Sailing With Phoenix | Oliver
Here is my team! And my plan! Shout out to my dad and @SailingIntoOblivion  aka Jerome Rand.
Sailing With Phoenix | Oliver
I Finally Sailed to Maui — Where It All Began
Sailing With Phoenix | Oliver

I Finally Sailed to Maui — Where It All Began

We set sail from Hilo to Maui with light winds 90% of the way, finally catching a chill downwind run. I reflect a little bit on why I love sailing so much and how the hard work does eventually pay off. After arriving in Lāhainā we battle surf breaks to get the dinghy ashore and then hike a wild loca...
Giving my boat Phoenix away. NOT MY KITTY PHOENIX lol for more details read caption on my instagram.
Sailing With Phoenix | Oliver
A Sporty 350 Mile Sail from Kona to Hilo 🌊
Sailing With Phoenix | Oliver

A Sporty 350 Mile Sail from Kona to Hilo 🌊

We battle big waves, broken gear, and beating to windward while sailing from Kona to Hilo on Hawaii's Big Island. This one was a doozy for sure. I also chat a bit about buying the new boat. More details on this very soon. And as always thank you for watching! ⛵ Join the Crew + Follow Along: 🌐...
Here we go again.
Sailing With Phoenix | Oliver
We Broke Down in the Middle of Nowhere on Hawaii’s Big Island
Sailing With Phoenix | Oliver

We Broke Down in the Middle of Nowhere on Hawaii’s Big Island

Nothing ever goes to plan, but that's half the fun. What began as a laid-back drive to the volcano quickly turned into an off-road adventure through lava fields, green sand, and a broken-down Jeep miles from anywhere. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s P...
It is true that because of you I get to chase my wildest dreams. I am forever grateful.
Sailing With Phoenix | Oliver
I have not made this decision lightly. I’ve spoken with my family. They know what this means.
Sailing With Phoenix | Oliver
Sailing 220 Miles From Oahu to the Big Island
Sailing With Phoenix | Oliver

Sailing 220 Miles From Oahu to the Big Island

A 220-mile sail from Oahu to the Big Island became a lesson in patience and respect. Between calm seas and sudden squalls, we were forced to change course — the sea had other plans. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instag...
Don’t be most people.
Sailing With Phoenix | Oliver
The life you want lives in the other side of hard work. Always.
Sailing With Phoenix | Oliver
I Tried Sneaking Onto Hawaii’s Most Epic Sailing Canoe Race
Sailing With Phoenix | Oliver

I Tried Sneaking Onto Hawaii’s Most Epic Sailing Canoe Race

Huge thanks to the Hawaiian Sailing Canoe Association for inviting me out to watch this incredible race 🙌 Learn more: | ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instagram 🎵 TikTok 📘 Facebook #hawaii #hawaiiansailing #ca...
Thanks, @Friskies, for the resupply from Costco and supporting Phoenix and I. #ad #FriskiesPartner
Sailing With Phoenix | Oliver
First time in a helicopter. Totally one of the coolest experiences of my life
Sailing With Phoenix | Oliver
Full circle moment.
Sailing With Phoenix | Oliver
Fixing the Engine Before Sailing to Hawaii’s Big Island
Sailing With Phoenix | Oliver

Fixing the Engine Before Sailing to Hawaii’s Big Island

I’m preparing to sail to the Big Island — but first, my diesel engine throws me a curveball with a leaking raw water pump. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instagram 🎵 TikTok 📘 Facebook #BoatMaintenance #SailboatLif...
I’ve sailed 1,000 miles on Phoenix around the Hawaiian waters since arriving here from Oregon.
Sailing With Phoenix | Oliver
Scuba Diving at Electric Beach Oahu 🐠
Sailing With Phoenix | Oliver

Scuba Diving at Electric Beach Oahu 🐠

I'm back in the water at Electric Beach, O‘ahu, one of Hawaii’s most stunning dive spots! 🌊🏝️ This time I’m joining Sam and Jamie for more scuba training… and we found a lot more than just an anchor! 🐢 Follow Sam & Jamie for more amazing dive adventures: 👉 Jamie Underwater Photography: 👉...
Learned more about windward sailing in 3 days than in the last year combined.
Sailing With Phoenix | Oliver
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