Can this guy really make it to Hawaii alone? Solo sailing super noob sails to the Oregon Coast.

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Last year, I walked away from the corporate grind. I quit my career of 11 years, liquidated my 401k, and stepped into the unknown. It took three years of battling fear and facing the reality that, as a result of my cervical spine condition, I'm at risk of paralysis. That truth pushed me to finally choose a life worth living. I hated my job. I despised the corporate machine.
But I have always harbored a wild, impossible dream: to sail around the world. So I quit, bought a sailboat, and threw myself into a life I knew nothing about. No sailing experience. No roadmap. Just blind faith in a better future.
Now, I can confidently say my life has never been better. Follow my journey as I learn to sail, outfit my boat, and prepare to sail around the world. The dream is alive, and I am making it real. I'm leaving from Oregon to Hawaii in May 2025!
#sailing #sailinglife #dream #boatlife

[@FelixDaHack]

Don't be so negative on yourself. What you're doing is so much more than a lot of KZbin arm chair sailors. Kudos to you. Not many people go out on a limb into the unknown and far away from the comfort zone... Trust me I know. I did thge same a few years ago and friends & family thought I was mad! Now sitting on my 2nd boat. There you go. Your content is perfectly fine and the rawness + honesty is a refreshing change. You got this without a doubt. Yes it's a steep learning curve but as I always say: you learn more from your mistakes than your successes. Don't get me wrong here, even I question my sanity with some damned difficult jobs on my boat but I always remember to look back from how far I've come. Love your work and am looking forward to more content ASAP! Fair winds from Australia 😊

[@Sailing_With_Phoenix]

You are amazing haha thank you for that comment! The cringe machine is a churnin so strap in 😂

[@grahamehill6128]

Two black balls = isolated danger, safe water around it. Keep jacklines as close to the centre line as possible. You can limit the movement by attaching them at the mast. It always helps to make a passage plan before any trip, bridge names , navigable spans, heights, hailing channels etc., Single handing requires preparation especially when docking. Whenever possible, always head into the flow when approaching the dock, this gives you maximum steerage with minimum speed.

[@brikler7717]

Sounds like solid advice. I'll be reading your comments, to assist me in my future adventures myself.

[@Sailing_With_Phoenix]

@@grahamehill6128 yeah man great advice thank you! The more time goes on the more i look back and wince at the mistakes I’ve made haha plenty more to come. I really appreciate your input! I swear I’m learning to sail through my comment section 😂

[@AdminLogistics.]

Bro, you're doing it!! The videos will get better as you progress. Looking forward to the next one!

[@bufobryn]

I’m supporting you on all platforms! Keep posting you got this! 🤟🏼✨🤟🏼🤟🏼✨

[@Sailing_With_Phoenix]

Heyyy! Yes I know you from tik tok!! 😂 you are amazing! Haha thank you!

[@renaissanceman8564]

Middle aged man here ! Hey just can’t help mentioning to run a tethering line on the dinghy through the front eye,,,then down both sides to the back like to some handles or even the transom with carabiners. That way it won’t rip off the front eye in 500 miles . The other trick is a couple of pool noodles off the two stern lines forming a triangle so the line will float and not get wrapped around the prop. I used to drag mine back 30 feet but find it’s easier and calmer 10 to 12 feet back . Good place for my crab pots tied in under the seat. I Never tow my dinghy with the engine on in case it flips . Mine is on a kicker mount so I can move it back and forth or as a backup if my main dies. Jack lines down the center and the tether is short so you can’t go over . Dudes fall off taking a piss off the stern at night when they are drunk . You can drag a life line but for me ,,,,,never leave the boat,,,,Apocalypse Now. Ok,I wish I was you kind of or just 35 years younger Lol Good luck peace on earth and ocean.

[@Sailing_With_Phoenix]

Thank you man! I appreciate the advice!

[@Mr.T-BAGGIN-UR-MOM]

Your videos are going to help me big time in my own sailing future. I envy you and im looking forward to being in your shoes one day. I seriously appreciate you putting yourself out there and not acting like you know it all. Its very inspiring. Good luck brother, maybe ill see you on the water someday!

[@Sailing_With_Phoenix]

@@Mr.T-BAGGIN-UR-MOM thank you so much man! I will without a doubt see you out there!

[@InterstateVet]

You did a great job, and I’m looking forward to your future videos!

[@Sailing_With_Phoenix]

@@InterstateVet thank you!

[@Septix]

Rooting for ya dude, heard so many stories about sailors who had some medical condition right before they're big plans that I'm hoping to make a similar move as you. One guy near where I used to sail spent over a decade building a world-class trimaran only to abandon his cursing plans after a serious health condition he only found out about during sea trials... all those years down the drain. Fair winds!

[@Sailing_With_Phoenix]

Thank you man! My medical condition is exactly why I am here

[@vokeswaagin]

Killin it bro! I'm excited to follow along and see what more is in store!

[@Sailing_With_Phoenix]

Thank you!🙏

[@michaelgarrett20]

Great stuff man, loving watching your journey!

[@Sailing_With_Phoenix]

Thank you man!

[@Rainmaker60LM]

you have to set up your jack line and harness so you CAN NOT FALL OFF THE BOAT. You will get dragged and die if you are in real seas and moving more than 3-4 knots.

[@randallferret2581]

Solid video !! 1k subscribers !! It's happening .. awesome !!!!!

[@Sailing_With_Phoenix]

🙌

[@canonen100]

I would look at some of the videos about how to get back in the boat. My boat has an open stern so pretty easy. I’m glad you got the gear.

[@Sailing_With_Phoenix]

@@canonen100 thank you man yeah I need to check that out!

[@NCmountainview]

Congratulations on starting the journey. I am happy to be here from the start! Good luck!

[@Sailing_With_Phoenix]

Thank you! 🙏

[@bowersish9489]

I'm happy to see your journey unfold, im sure you'll learn lots but look at yourself living your passion. Great job

[@Sailing_With_Phoenix]

Thank you haha I love this life

[@brikler7717]

Will be interested to watch your adventures. Best of luck and stay safe. Fair winds.

[@Sailing_With_Phoenix]

@@brikler7717 thank you!

[@bryanfriend7642]

I have made that trip about 18times now. As well on multiple sailboats . Will be there in about a month on our aluminum pilot house

[@Sailing_With_Phoenix]

Nice see you in a month lol

[@K4g4m1]

I'm watching every episode the day it comes out. It's better than you give yourself credit for. :D

[@Sailing_With_Phoenix]

Hey thank you! 🙌

[@AllTerrierMotives-p7m]

Discovered your journey on Instagram a while back and I'm totally hooked and in awe mate. Good on you for escaping that crappy corporate world and embarking on a life changing journey and super exciting chapter in your life. I reckon you must have some super proud family and friends back home! Looking forward to travelling on your journey vicariously through KZbin and Insta. It's been a dream of mine to just take the leap you have taken and perhaps your journey may just be the inspiration I need. Wishing you safe passages and fun times wherever your dream takes you. Keep on keeping those videos real - its very refreshing. Cheers and all the best from Jeff in Melbourne, Australia. P.S. Love the boat and your cute little travel companion!

[@Sailing_With_Phoenix]

Wow thank you! And just go for it haha don’t think too much. Thinking stops us from doing the things haha and my god if I can do it literally anyone can 😂😂 thank you for your support it truly means helps ❤️

[@acactual8278]

Run your jackline elevated down the center of the boat by the mast. FYI: Most Sailors cannot pull themselves back onto the boat. Some say it's impossible. I shortened line to where I couldn't fall over

[@Sailing_With_Phoenix]

After reading all of these comments I’ve actually got an idea now that I think will work well but will require me to get a second set of jack lines

[@canonen100]

One thing that you can practice really easy is heave to. It’s great if you need a break need to fix something. Or to weather out a big blow. Tom cunlif is an old sailor with some great videos.

[@Sailing_With_Phoenix]

@@canonen100 I’ve practiced some but it’s very difficult on the river haha not a lot of room to mess around. But now I’m in Warrenton I should have plenty of room. I am excited for that

[@martwick]

That is a hazard buoy, they mark things like ROCKS or other hazards. Usually you should give it another foot or two. BTW this is Tallulah, fair winds Oliver!

[@Sailing_With_Phoenix]

@@martwick 😂 oops! Hey man! Thank you! Haha

[@MISCIFMAKER]

Good video jack line test , he also had a rope latter on starboard side it was a real struggle

[@Devon_Dan_Sailing]

Excellent video! Can you maybe put a map up of your route for us foreign folk! Love it though

[@Sailing_With_Phoenix]

I can certainly try and figure out how to do that! Haha

[@MISCIFMAKER]

Dude has balls , crossing the bar in Astoria , may not be the worst of this journey. West coast passage may be consider tougher than the Cape horn in winter months let alone calm seas , 30 knots out most of oregon sail. He needs to be in S. Cail b4 APRIL ILL enjoy watching.

[@elsydro8064]

Dude this is amazing, great content

[@Sailing_With_Phoenix]

😂😂😂 thank you!

[@PJumper727]

Just subscribed. Brother enjoy that youth and stay original. Looking forward to following you! 🤙

[@Sailing_With_Phoenix]

Thank you!

[@thewaterheaterfactory]

I cant wait for your Hawaii trip - What port are you leaving from?

[@Sailing_With_Phoenix]

Me neither 😂 I’m ready to be warm haha I’ll be leaving from Warrenton marina

[@305clearwaterways]

Beautiful ❤

[@scralet017greer3]

Hell yeah bud. When you get to st.hellens, let me know. I'll sail out and bring a beer.

[@Sailing_With_Phoenix]

@@scralet017greer3 😂 man I’m already in Warrenton!

[@Rainmaker60LM]

put dock lines away because if part of one goes in the water and its upfront it can get under the boat and into the prop. stored aft like this if one dropped partway in the water and you had to stop and reverse you could get it wrapped up in the prop. best practice is to coil them and tie them off to something on centerline of the boat or put them away below deck if you have storage somewhere accessible from on deck

[@Sailing_With_Phoenix]

@@Rainmaker60LM yeah that’s good advice haha thank you

[@Rainmaker60LM]

@ you probably think I’m so annoying by now. I’m rooting for you, want to help get you there safely

[@Sailing_With_Phoenix]

@ 😂 no man not at all I’ll take all the advice I can get lol

[@shaneparrish9991]

Good practice to have 2 dinghy lines to different areas of dinghy. Just incase one let's go....

[@Rainmaker60LM]

Bouy looks like an isolated danger bouy for a wreck or rock. Ive never seen one but looked it up. You might want to steer clear in the future.

[@Sailing_With_Phoenix]

@@Rainmaker60LM 😂 yeah man i should not have got so close haha well now i know! I live to learn and sail another day 🙌

[@renaissanceman8564]

Day one in the can ! Docking can be a bitch solo. Wind pushing you , currents and you are tired .,So,, an easy way is a line from a center cleat and you can bring it into the cockpit. Around a piling or dock rail or cleat then jump back on the boat, tie to the boat , put the boat in reverse no throttle . This works well so if the boat is slowly backwards when it’s windy, the center cleated line will hold the boat to the dock. Put out two bumpers or a ball on the stern side dock side well before if you are going to attempt this. Leave the engine running until you are tied off ,,,,maybe. Then and only then bow line stern line. On a calm day if you had an empty dock like this one you could practice docking approaching , get to know your abilities, improve your confidence. On the next video ,,,,I will tell you two ways to impress the ladies. 😮

[@Sailing_With_Phoenix]

😂😂😂 awesome. There are some docks empty docks all over here at this marina and the marinas around plenty of safe places to practice and I think that’s exactly what I will do haha

[@lucastisdale2667]

do you have a lee cloth for your bunk? also you're not bad at docking from what I see. don't forget fenders before coming in and you should use nylon rope, or something that stretches to tie up. I personally wouldn't pay for a one night slip in the middle of winter that's all I'll say.

[@Sailing_With_Phoenix]

Hey thanks man haha I don’t have a Lee cloth yet but it is on the list!

[@rende2851]

You're on your way. Saw your boat was gone from the sllp and thought that you were just out for an overnight but I saw this and was like yep he's gone. Good luck. On the dingy you might want to get a poly line for it. Having a line that can sink anywhere near your prop is not a good thing. I usually will use a heavier line like 5/8ths and one that is brightly colored so I know where it is and others do too. I've had wind surfers and Jet skis try to cut between me and my dingy in the past. Btw did you get it patched? You can run your jack line from the cockpit around the traveler base stands then to the mast to the mast, Then run another one from the mast to the bow cleats and you normally want two clip ons. Sorry we didn't chat more when you were here but I will be following your adventure.

[@Sailing_With_Phoenix]

Hey man you found me! 😂 no I havnt patched it yet I just pump it up every few days! Thats great advice! I think I know exactly how I will set it up now but will need to get another set of jack lines. And no worries man! I’m a pretty keep to myself person haha

[@Gman11962]

Keep em coming brother lol

[@Sailing_With_Phoenix]

I will! I am incapable of stopping lol

[@bigchief4044]

Noice!! Excited for you. 👍

[@Sailing_With_Phoenix]

@@bigchief4044 thank you!

[@MiaHeidenstedt]

Hey Phoenix really nice to see you doing this good and reflecting and improving! I want to mention some things that i noticed because i like your videos and you are sympathetic and i do not want you to experience very negative situations: Other ppl have great advice on the life line (jackline) so i am not going into it but there is a good video about a person that tried to get back in the boat while being over board and on a life line. It is very very difficult because of a wall of water that pushes against you with a few knots. This person only managed to do so because they had a rope ladder that allowed them to use their legs to lever themself out of the water. This water looks slow, but it has a lot of mass and you have a lot of surface, do not overestimate yourself, play it safe with this one. (Edit here is the video: kzbin.info/www/bejne/anqXiHmXntCLp9U ) Cool idea to try it out with other ppl on board! This would be a fun video! Keep a look at the propeller that it cannot reach you if you hang in there when doing so. 16:01 is likely a en.wikipedia.org/wiki/Lateral_mark which signal the canal position. This can be important for you because your boat has a deep keel. Check about depths so your keel does no go aground. The glasfiber boats like you have one can take great damage by going aground. Like 10's of thousand dollar damages or complete loos of the ship. Keep informing yourself about how to stay on the boat, about AIS (before you go to blue waters), about how to survive a storm and bad whether. Maybe something that is often overlooked and in my experience brings great danger is the behavior of the boom. This thing can, if you make an error or the wind does funny things, just yeet to the other side building great momentum and break the rigging, the mainsheet traveler or you if you stand in the way. This thing also yeeted sailors from their boats. If there are strong winds it can be impossible to reef the mainsail. "If you’re thinking about reefing, it’s already time to reef." You are doing a great job Phoenix and fair winds!

[@Sailing_With_Phoenix]

Hey thank you for the advice! She’s only got a 4ft draft! Thank you so much again for your input!

[@frank4one]

You don't have a clue what you are doing. You remind me of me. Enjoy yourself and keep the videos coming. 😅

[@Sailing_With_Phoenix]

@@frank4one not even on the slightest haha

[@InterstateVet]

Did you quit your job yet?

[@Sailing_With_Phoenix]

@@InterstateVet didn’t exactly quit haha but I’m no longer employed! 😂

[@InterstateVet]

@ nice! Enjoy it! I’m sure you are!!

[@pietvanstom3079]

mate if your put your channel email in your about section i can email you my pre ocean crossing check list ..u need to go over this ..might save your life ,,3 circumnavs i learnt a lot ..ps u r hilarious : ) in a good way

[@Sailing_With_Phoenix]

😂😂😂 thank you! I’ll just put it here and then put one up as well! But it’s [e-mail]

[@pietvanstom3079]

also companies will start sending u free stuff

[@Sailing_With_Phoenix]

I sure hope so 😂😂😂 this is expensive!

[@RileySperbeck]

Hey bud solo 25yr old sailor with his cat up in WA, where’s your next destination?

[@Sailing_With_Phoenix]

@@RileySperbeck in this video and the next to warrenton! For the last stage of the refit. Then Hawaii in May