I’m sailing hard on a hard wind, though then again the wind always feels a lot harder when your hard on it and there’s always a certain point when I’m too close for comfort to it. Now a dark cloud is here and it’s changing the direction of everything. All these squall clouds coming and blowing and doing me dirty! I’m on a starboard tack which is not my best side, I can point much higher on a port tack. Why the heck is that? I suppose everything in life has a better side. Doesn’t it? Like beds and people and islands and feathers and waves. 

It’s very sporty sailing this time of year around here. Very very very very sporty. And every pass around here is harrowing, it’s like squeezing my boat out of a birth canal that has a bunch of extra appendages inside of it. The beauty of this higher wind sailing is that the swell is cleaning the green algae beard off the sides of my boat for me! 

I am trying to get back south. There is a harvest festival on the dog shaped island (Malekula) that I am just jonesing to see. The masks that the men wear for the festival are like something out of the future past. The trouble is the wind is blowing predominately from the south and I’m on Espiritu Santo, which is north of the dog, so it’s impossible to go south without a million zigzags. My plan is to hop my way as east as I can, then bust a hard move to the southwest. I suppose I’ll get there if the stars are all aligned. If not I’ll end up somewhere else just as cool. 

A flood of flying fish just flew over the bow of Juniper. They were big old suckers too. About the length of my elbow to the end of my fingertips. I swear. I swear. I swear those fish were “this big!” There’s such romance in a scene like that. It’s as romantic as sitting around and listening to the birds talk about trees. 

I suppose I should tell you what I’ve been up to….

I was in the mermaid blood colored bay for two days. I never did see the shore. It rained a lot and I collected it. Every night I could hear the dugong beneath my boat making the sounds that creatures make when they make love. That was romantic too.


From the dugong bay I sailed up to Oyster Island. I’m buddy boating with my South African friends from a catamaran called  Aventure. The pass into Oyster can only be entered at high tide, so we all woke up before the sky had any color in it in order to make it on time. 

I’m inside the pass of Oyster now. It’s a winding narrow snake with a tongue and venom and everything. I’m following Aventure and both of us are following some other boats gps track, but Adventure appears to be going rogue from that track and I don’t know what to do. The snake is getting me twisted. I can see three buoys marking who knows what and I’m not sure what side of them I need to be on and I can see lots of coral bommies too and I don’t know how deep they are. My depth sounder alarm is going off. Beep. Beep. Beep. It reads 2.5 meters. I’m pissing my pants and touching wood and all that jazz because that means I’m only 2 feet away from my keel touching bottom.

Yea I just went from feet to meters. That’s right. So what. My depth sounder reads in meters and my mind reads in feet. It drives all the other sailors mad that I don’t just change my depth sounder to feet instead of having to do the math all the time. But hey, this boat ain’t their boat and my head ain’t their head. 

I get to the anchorage unscathed, except my heart, it’s a whacked out weirdo… always. There is a derelict sailboat anchored in the bay and another one that is bottoms up on the shore after a cyclone had it’s way with it, all I can see is some lime green paint and half a hull. The water of Oyster is grass green and there are forest green mangroves all around. It’s all green green green. 

The Aventure gang and I blow up our paddle boards and head up a river that rolls through the mangroves. The current is against us, but that doesn’t matter. We pass flowers and trees and bridges and fishermen. The river changes from green to blue as we go. An hour comes and goes. The end of the river is a sapphire blue hole with a banyan tree growing along one side and there are rope swings and slides. The end of something is always the beginning of something new, remember that.

This entire place is some storybook fairytale. The water reflects the sky, reflects the trees, reflects my mind and we just ate those psychedelic chocolate chuckles that my friend sent me in the mail way back in April so everything is getting weirder and way more reflective. Sky upon sky upon earth upon water upon sky upon sky upon water upon earth upon water upon sky upon sky. 

Bloody hell it’s like I’m tangled up with a rocket ship. I can’t even hardly spacewalk. All I can do is turtle around and I regret having had any morsel of chocolate at all. I want to throw up. I want to hide from myself and these other people. I must eat. I eat. One granola bar. It taste like plastic. Still, I feel better. 

One of my friends is a hyena. I have to excuse her to the other people at the blue hole. “She’s not laughing at you. It’s me. I promise.” My other friend just face planted into the blue off of the highest rope swing. Ouch! The banyan tree has five wet-clothed Vanuatu girls lounging on it’s wide roots. There is some creepy French guy and every time I turn my head he is right there, as if he is made of air and can be everywhere! Meanwhile, I’m in a hypnotic trance over the reflections on the water.

Every living thing has a pulsing glowing wobble to it and the trees are singing a show-tune. I think the chocolate is gonna take me to the feet of God and she’s gonna tell me what I need to do. I’m at this crossroads you see and the only thing I can think about is the race. It consumes every ounce of me. It wakes me up at night and floods my head. I don’t even like racing, but I want this bad, and I’m afraid of wanting it. It won’t be easy. 

I want to know God is with me on this. I want to know that I won’t pitch pole. I want to know what conditions I’ve already known and survived because it will help me decide. Earlier today I asked my godfather if he knows the strongest wind conditions and swell I’ve been in- how on earth does anybody measure swell height from the boat? All I can tell you is that when I’m in the trough of the wave sometimes I’m looking way up high, but how high? I don’t know! Anyway my godfather said, “Oh you’ve been in some awful stuff. On the map those storms look evil. Like Mickey mouse ears all twisting around you.”

I really do wish you could see the blue of this hole. 


Some more boats arrived to Oyster Island a day ago. A race boat called Nonstop and my buddies on the catamaran Isis. All New Zealanders. The captain of Isis reminds me of Owen Wilson. He’s all energetic and funny like that and he wears short ocean blue swim trunks with shrimps all over them paired with a sky blue button down top with pineapples all over it. His wife is the most gorgeous 50-something you’ve ever seen and one cold morning she cut my hair for me. 
All of us boats are leaving Oyster at the same time. We are a train parading around the snake, holding our breaths. Nonstop losses their engine for a moment, then they get their keel rapped around one of the buoys and have to cut it off. Glad that wasn’t me. 

Eventually we all make it out alive. Aventure bashes east and the rest of us washing machine our way out of the main pass and fall off north to Hog Harbor. Woo Pig sooie. 

I am hand steering. Moving along at 6 knots. All day. I pull into Hog Harbor at sunset. It’s another mermaid blood type place. My anchor gets caught in the chain locker when I go to drop it. Half of it is hanging down and skidding along the bottom of the sea floor and it sounds like a construction site as I run down below to unkink the chain. By the time I get the chain down I’m pretty deep, but I roll with it. 

At night giant glowing clouds of bioluminescence move across Hog harbor all jelly-like and at a certain point they just disappear. To see them is so otherworldly and mesmerizing that I didn’t know if I was dreaming them up or what, but the other boats saw them too. 
The beach next to Hog is called Champagne Beach. In certain places the sand bubbles like all effervescent things do and it is the softest sand you’ve ever felt. Soft as silk. While sitting on that beach I realize that that  special place where the sea meets the sky is all we ever needed to heal all that was ever broken inside of us. Cheers to all those new horizons. 

I talk to my mom. She says, “I wish you were a land bird instead of an ocean fish.” I imagine that for a land bird to have given birth to an ocean fish, was probably like giving birth to a Martian. Speaking of mom’s, did your mom ever say, “N-O. No! What don’t you understand about the word ‘no’?” I don’t think I ever understood anything about the word “no.” Still don’t. I only know Yes. Yes. Yes. 


I’m heading to Dolphin Island. The wind is a strong dose today and It takes me 45 minutes to get my chain up. Nonstop comes on the radio saying their chain is wrapped on coral and two minutes later I realize mine is too. It won’t budge. Nonstop is getting in the water and I’m trying to sort out what to do for myself when low and behold a gust comes and breaks my anchor free from whatever shackled it to the bottom and my bow blows downwind. God bless the wind! 
The water between Hog Harbor and Dolphin Island is vicious. There is a massive side swell with inconsistent winds. I hate an inconsistent wind on my wings. I hate an inconsistent anything. There are crazy gusts too. One minute it’s blowing 15 knots and the next 29 knots apparent. And the wind is behind me, so that’s almost a near gale. I forgot to put on my hydrovane so I am hand steering and it takes all the focus I can muster. With no main and only an itty bitty bit of headsail out I am doing 5.5 to 6 knots and rocking wild down the waves. 

I get on the VHF and say, “Glad we decided to move anchorages during a near gale dudes.” 

It’s two hours later and I’m anchored right next to Dolphin Island. It’s a little paradise. If you look at Dolphin on the satellite map it appears to make a frowny face. The color of the water around it is so pretty that it makes you want to fall into it no matter how cold it is, so I can’t for the life of me figure out why Dolphin looks so tragic. There are some cows living on Dolphin and at night time I can hear them moan. They sound sad too. 

I walk around Dolphin looking for the cows. There isn’t much to report- some palm trees and limestone cliffs and a bunch of dung with nothing psychedelic growing out of it. There is a little sand spit that reveals itself at low tide. We collect drift wood and make a fire. 

Port Orly town is across the bay. It’s got a few thousand people. I go there looking for vegetables and a place to burn my trash. This town is like something from the future past. Imagine the settlements from the Gold Rush on another planet in the year 3023. I see people riding bikes down dirt roads. Traditional huts mixed in with concrete houses. I see one house that is three stories tall with porches wrapping around it and everything! Oh and you should see the flowers growing here, purple firework looking things. 

There are women gathered in a yard digging through a trash bag of thrift clothes. One woman with a baby over her shoulder is holding some purple sequin number that I am drooling over.  I miss wearing sequins. Sequins in the sun. Glorious. 

I find the vegetable market, which is also a kava bar. They’ve got cabbage, bananas, pamplemousse, green peppers and fresh baked bread rolls with butter dripping off of them. There is round man cutting up peppers into a bowl and it’s a strange site because in this country I only see women do that. Next to him there is laptop on a wood table playing music. Across the road there is a store with some staple items like rice plus a fridge full of beef. There is a man in there sitting in a chair watching a French action flick that involves a lot of guns and blood.  


Anyway that was a lot of stuff to tell. It’s  5:30 PM and I’ve been on the water since 6 A.M. and now I’m in the shadow of the land without wind and  here comes night with all its confusion. Lights flashing and I don’t know if they are boats or what. There is no moon. I feel like I have a bag over my head. I am almost to an anchorage. I see a spotlight flash across the clouds. I see many more little lights blinking all along on the water. Now there is a stadium like light and it’s shining right on me. It’s blinding me. I want to go back inside the black. Beneath the stadium light is a green light which means the thing is coming at me. I don’t know how fast. I slow down. What the freaking! It passes. Right off my bow. So close. It’s a bloody barge! 

Xoxo O

P.S. – I’ll look for you in my dreams

P.S.S. – It’s really dark out here tonight, even with my eyeglasses on I can’t see much. 

*Massive love to all of you who have sent things from the Amazon wish list! I don’t know who you all are yet, but my mom said packages have been arriving and I will be home in November to send you notes!  

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4 Replies to “HARD ON A HARD WIND”

  1. I love your writing, always interesting and dreamy descriptions, great photos and videos. Thanks for sharing. I love the end of something is always the beginning of something new. Thanks for sharing your positivity. Хохо Mom

    1. Some of your adventures sound quite scary, but you have proved over and over. What a terrific sailor you are. I love hearing your stories and getting to see you. Love you always.

  2. ‘Love reading your updates, especially when you include photos, it helps put us there with you.

  3. I am so totally with your Mom on loving “the end of something is always the beginning of something new!” You are always so full of wisdom, Olivia! And oh, dear goodness, how I just love your writing!!! I also love how you share your tender heart with us and all the life lessons the sea teaches you! Love you!💜⛵️🌞🌊

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