Sailing the Pacific - 1st Passage: San Francisco to Hawaii

Ever since I dreamed up the Routes of Change project 8 years ago I had been thinking of crossing the Pacific Ocean. I was initially planning on doing it in a rowboat. Those plans ended up taking me on several expeditions with OAR Northwest. You can read all about them here. Having learnt what it takes to fund and organize an Ocean row I started this expedition being much more open to sailing across the Pacific. In other words it takes too much money and time.

Plan A was to crew on a sailboat that was in need of help for the crossing. This would be the easiest, cheapest, and what I thought would be the most likely option. There are many crew seeking sites online and it’s common for people to be looking for help for long Pacific Ocean passages.

Plan B was to join an Ocean rowing team that was in need of another rower. This was a bit less likely but I did have proven experience. The previous year I had also been called out of the blue to join someone on a row from San Francisco to Hawaii. The timing wasn’t right and it didn’t end up happening.

Plan C was to help build a viking ship and sail up to Alaska, then kayak or something of that sort across the Bering Sea. The least likely option. A friend had mentioned that there was a team dreaming this up and they were in need of help and crew. It seemed to be in the very early stages and unlikely to happen anytime soon.

A week into the journey while paddling a canoe in southern Ontario I was introduced to a friend of a friend who had been planning to cross the Pacific in his 1968 Alberg 30 sailboat, Dolce. I spoke with the captain, Dave, over Skype and he was up for sailing with me and not using the motor. We planned for me to meet him in San Francisco in about 8 months. Plenty of time for me to make it across Canada and down the west coast. Plan A Check!

Two weeks later a friend in the Ocean Rowing community invited me to join her in the Great Pacific Race. It would be just the two of us in a 29 ft rowboat from California to Hawaii. I was tempted but for several reasons I decided to pass. I had already committed to meeting Dave and he was up for sailing all the way to Asia. The friend would be stopping in Hawaii, leaving me to figure out a way to get off the most remote island chain on the planet. I also barely knew this friend and had no idea how we would get along on a very uncomfortable, long, and challenging ocean row. Sailing with Dave would be the more comfy option for sure.

Dave had been working for Facebook when he decided he wanted to sail the Pacific. Without previous experience he purchased a boat and taught himself how to sail by reading books and watching youtube videos. Dolce’s home port was on Lopez Island so her first real test with Dave at the helm would be cruising her down the coast from Puget Sound to San Francisco. On this passage Dave became extremely sleep deprived and came to appreciate the option for having crew on board to take shifts with.

I showed up in San Francisco more excited than normal about adventures to come. I had enjoyed a beautiful, but much too fast, ride down the coast (see this blog). A friend had introduced me to friend who lived in a funky communal living space. They were very welcoming and offered me a space to stay while in the city. The next day I met Dave very briefly in the street and we had an awkward hug (mostly because I was filled with gratitude for him and partly because he gives shorter hugs than me. haha). I didn’t get to see the boat that day as he had anchored it off of an island that was accessed by a bridge that cyclists and pedestrians were not allowed on. I would have to be patient.

San Francisco is filled with interesting people and I was in need of some organizing before heading out to sea so being patient was not a problem. My timing aligned perfectly with an event that is a dream for me. The Decentralized Dance Party. It was way too much fun to dance through the streets with a roaming crowd of funky people in costumes with music blasting from hundreds of boom boxes that had been distributed throughout the crowd. Simply dancing through the streets would have been fun enough but we also danced our way up spiralling walkways, across bridges, and around beautiful cityscapes. It’s a dream for me to one day have Routes of Change arrive in every new town to a Decentralized Dance party through the streets. It was by far the most uplifting and fun experience of the journey so far.

When I finally got to meet Dolce it felt a bit surreal. Dave had docked her at a marina that was right beside the San Francisco Giants stadium and there was a baseball game happening. I could hear the crowd roaring and expected a home run ball to fall on the boat at any time. I stepped on board very delicately but in my mind I was wanting to hug the 5 ton boat. Was this really happening? Was I about to sail across the Pacific Ocean? Was it all a dream? I’m still not sure. Someone please slap me!

After a few days at the dock gathering some final supplies we decided to sail over to Sausalito where it was free to moor the boat. Dave and I were both a bit nervous about maneuvering in the busy San Francisco Bay. The wind was blowing strong as we sailed past Alcatraz. I thought it wouldn’t have been that challenging to escape by swimming to shore from the island. Sure the water is cold and there are currents but if you’re swimming at full steam with freedom on your mind it would be a small challenge to overcome. We pulled in amongst hundreds of other boats in varying states of decay. Dave was concerned about the quality of their lines and the likelihood of them drifting towards Dolce.

Over the final few days I was visited by a few different friends who happened to be in the area and wanted to wish us the best. They were both excited and fearful for my journey ahead. Chocolate, wine, and other goodies were gratefully added to Dolce’s hold. After big hugs and a few tears we said goodbye for what would likely be a few years or more.

Before leaving Dave and I had one of our few disagreements. We didn’t have a watermaker on board so I thought we should be carrying plenty of water. Dave seemed to think we didn’t need much. He ended up asking his expert cruising consultant who recommended bringing even more than I was suggesting. We ended up buying more containers to carry water. In the end they thankfully were not needed.

The high winds and rough seas that Dave had wished to avoid were forecast to subside over the next few days so we decided to set sail ASAP. We got a slip at a marina for the final loading of water and provisions. It was a sunny and calm morning in the bay when we set sail. Setting sail is not the right choice of words because a calm morning meant no winds. I pumped up the inflatable SUP and paddled after Dave as he motored Dolce out of the crowded Sausalito bay. I paddled past a group of other paddleboarders who smiled regular old smiles. I couldn’t help but think that they would be the last people (other than Dave) that I would see in a long, long, time. If only they knew that the next land I was going to touch was 2,200 miles away in the middle of the Pacific Ocean. Maybe I would have got a hug or a kiss from some of them. I would have liked that.

As I paddled out of Sausalito the wind was yet to pick up enough for Dave to feel comfortable with sail power alone. San Francisco bay has lot’s of gigantic ship traffic and the currents under the Golden Gate can be very powerful. I was happy to paddle under the bridge anyways. It was a very special moment to be leaving North America by SUPing under the Golden Gate Bridge. I looked up and saw some of the tourists looking down. If only they knew...

Shortly after we cleared the fast currents that flow under the bridge the wind picked up and Dave cut the motor and raised the sails. I climbed on board and off we went into the relatively pacified Ocean. Next stop Hawaii.

Or so we thought. After an hour or so of sailing the wind died and we were vulnerably floating around on the edge of major shipping channels. We decided to head into Bolinas Bay for the night and wait for the wind to pick up. We dropped the anchor and kept up a watch in fear that we might drag our hook into the breaking waves and onto the beach. The hook held fine and the next morning we raised the sails again.

We sailed most of the day but in light winds and strong currents. Come nightfall the wind had died once again and we were left floating directly in the middle of the main shipping channels. We had our AIS on to make sure the ships would not run us over but there was certainly no guarantee that we were safe. It was a long 4 hour night shift watching the lights of big ships as they thankfully diverted course to avoid plowing us over.

The wind eventually picked up early in the morning and we finally made our way out of the shipping channels and further offshore. We sailed to the edge of the continental shelf just south of the Farallon islands before the wind left us once again. It seemed like perfect timing as we soon heard and smelled the loud breaths of the largest creatures on earth.

Okay, they weren’t blue whales but they were still massive and amazing relatives. Grey and Humpback whales were everywhere around us. They seemed to be happily feasting on the plethora of food to be found on the edge of the continent. The water was glassy and seemed inviting so I hopped in for a dip careful not to get swallowed by a whale...whatever that means.

A tiny yellow bird also joined us at this time. It was surprising to see such a tiny non sea bird so far out at sea. I was bit concerned that they had been blown off shore by the wind but considering there was barely any wind it didn’t make much sense. It took a brief rest on our boat and was soon off exploring again… or doing whatever it was doing. Beats me.


This ended up being the last calm we would experience for a very long time. The glassy water surface became interrupted by tiny ripples at first. It came in gusts and patches but soon it was clear that it was time to raise the sails. Within minutes we are cruising comfortably on a direct course to Hawaii.

The comfort would not last. Over the next two days the wind gradually increased. First reef, second reef, third reef. The practice of reefing a sail was new to me. I was accustom to simply letting the sail out in order to lessen the power of the wind on it. I had grown up sailing mostly small single sail vessels in pleasant conditions. Reducing the area of your sails is an essential part of sailing in strong winds. Dolces reefing system was set up in a way that you didn’t need to leave the cockpit in order to put in a reef. It worked okay but there was plenty of room for improvement. 

Shortly after reefing the sails as much as we could it was clear that the boat was still a bit overpowered by the wind. It was challenging to hold a course as the wind was gusting above 40 knots. Although not absolutely necessary, Dave and I decided it would be a good time to test out our storm gear and heavy weather tactics. We had both read up on a technique that had proven to be very effective for a well respected cruising couple. Considering we were both completely inexperienced with the technique we figured it would be a good idea to experiment and test it out. It ended up being an exhausting failure.

First we hove to, which is an essential offshore sailing technique for stalling the boat in place (with a minimal amount of downwind drift). We then deployed our sea anchor, a small parachute that sits below the surface and holds the bow of the boat into the waves. We also had a bridle in place in order to keep the boat at an angle to the waves and therefore diminish their force on the boat.

The book by these cruisers makes this technique seem simple in practice, and perhaps it is for their boat in certain conditions, for us it wasn’t working. Dolce was repeatedly tacking through the wind which would pull the bridle line under her hull and risk it getting stuck on the rudder or prop. After hours of trying to make it work with little success we eventually needed to cut loose the bridle line after it became stuck under the boat.

Dave was cold and thoroughly exhausted by this point and passed out on the cockpit floor. I kept warm due to the dry suit that I had on and because of this I was able to go out on deck in much more comfort. I kept a consistent watch for chafe on the sea anchor rode (rope/line). The sea anchor was not effective in keeping our bow into the waves and instead we spent the next 12 hours plus lying ahull. This meant that waves would all too frequently crash onto Dolce’s beam with a deafening boom and a force that threatened to roll her over. It was a very unexpected turn of events which made it all the more scary.

To top it all off I discovered how poorly waterproofed Dolce’s cabin was. Every time a wave hit us water would come streaming in through gaps in the cockpit hatch. There was also consistent drips coming from too many of the portholes (cabin windows). The cabin was not nearly as nice of a sanctuary from the weather as I had hoped or imagined.

Every couple hours I would don a harness and climb out the hatch as quickly as possible to avoid letting a wave enjoy the warmth of the cabin. Once on deck I would clip my carabeener to a strap running forward towards the bow. I would then crawl along the deck as the boat was tossed like a rubber ducky in the 5m seas. When a wave hit I would be temporarily in a waterworld with several serious thoughts in my head. The thoughts weren’t running through my head but rather they were posted up solid like anvils on my brain. How would I climb back onto deck if I were swept overboard and hanging upside down from my harness? How should I hold on if the boat were to roll and do a full flip? Would I be able to hold my breath and wait for it to roll back topside up? Or would I need to swim to the surface? hmmmm.

I never did figure out the answers to those questions. I scampered to the bow in the dark feeling like a character out of some wild seafaring epic. A bit surreal. If I didn’t have a look of fear on my face I’m pretty sure I had a smirk. I live for this sort of thing. When forced to survive I feel alive. I feel like my body and soul are doing what they were designed for. I feel alive.

Every time I made it to the bow I would let out a bit of rode and adjust the chafe gear to redistribute the tension. The force of the rode on the bow roller had bent it out of place quite significantly. Other than that potentially disasterous occurence, everything was okay.

After about 18 hours of this discomfort Dave arose from his deep recovery sleep and took the helm once again. The wind and seas had subsided so he pulled in the anchor, which had been tripped by the bridle line, and raised the sails. We were sailing again.

Minor damage had occured. One side of the dodger (cockpit cover) was blown out, the bow roller was bent, and the cabin and much of it’s contents were wet. Other than that we were good to go!

There wasn’t much sun over the next few days but when it finally showed itself Dolce took on the look of a bizarre ocean yard sale. Clothes and cushions sprawled across the deck soaking up the rays. Things are much more comfortable at sea when your stuff is dry!

When I’m not sleep deprived and the boat is not dripping with water on the inside I am very much at peace while at sea. When things are going smoothly there’s nowhere I’d rather be than cruising on the Ocean. When things are rough, the ocean seems angry, and the boat appears weak and vulnerable, there is nowhere I’d rather be but somewhere dry and not moving. This is not a feeling that you want to focus on though, and I never do while at sea. It would be a terrible mistake to focus on something unattainable in the moment. I focus on what I need to do to keep myself healthy and the boat afloat. I also tend to appreciate how crazy and gnarly the experience is, how grateful I am to be out there, how in tune with the elements I feel. 

After the storm Dave altered our course a bit further south and we soon were enjoying warmer waters and air. Arriving at the latitude of the Mexican border we turned directly towards Hawaii. We settled into the consistent 10-20 knot trade winds blowing us westward. Sailing directly downwind is something that we would later learn some sailors entirely avoid doing. The reason being that many boats end up rolling back and forth constantly. Dolce is small and she rolled like the best of them. I quickly became used to it but Dave did not find it very comfortable. He experimented with some different sail configurations but it didn’t really help.

We managed and were happy to be averaging 120 miles a day. Four hours on and four hours off. Reading books, listening to podcasts, and dancing to music. I was dancing at least. Whenever Dave was sleeping below Dolce’s deck became the sight of the best solo dance party in that part of the Pacific Ocean.

Dave and I would alternate cooking meals. Sometimes I would impress Dave by my creations and sometimes I would disgust him. That’s my creative cooking style for you. Apart from some of my failed creations we ate very well. No refrigeration on board but it wasn’t needed, until I caught a fish.

I had never done any true offshore fishing. I did my research thanks to Dave’s extensive library of over 100 books on board. I deployed a simple handline with some tuna lures that were gifted by some awesome friends in Tofino. The first time I deployed the line for a few hours I had no luck. The second time it took a couple hours for the bite to occur. What a rush!

I quickly yelled at Dave to come and take the helm while I grabbed the line and started pulling it in. For some weird reason whatever it was didn’t seem to be putting up much of a fight.

I only had about 50 feet of line out so it took less than a minute to pull it alongside the boat. By that time Dave had slowed the boat and was able to take the line while I readied the Gaff. As i looked over board I saw a big fat yellowfin Tuna and hundreds of its friends swimming along with us in the deeper water. It was a powerful scene. I wondered what it’s buddies were thinking. I realized that if they wanted to they could do some serious damage to the boat and us. Thankfully Tuna aren’t like that.

With one swing of the gaff I hooked the tuna by the head and hoisted it on board. It must have weighed about 40lbs. I quickly got my marlingspike and stabbed into it’s brain canal. I had read that this is the best and quickest way to kill a Tuna. Like with many animals the quicker you kill them the better the meat tastes. It was an intense experience for a rookie but I did it without issue. I then made some slits with the knife in order to bleed it out.

I hung it by its tail over the stern of the boat and thought about a massive shark stealing it from us. That never happened. After 15 minutes I brought it back on deck and fileted it. While I was cutting it up Dave was already busy preparing it in various ways to eat.

We feasted on tuna for a couple days. Tuna steaks, tuna tacos, tuna sashimi, tuna sushi, tuna vindaloo, tuna ceviche, tuna soup, too much tuna! It was a big fish and we didn’t have any refrigeration. Some of it went back into the Ocean to feed the fish before it was digested by us. We didn’t feel good about that and needless to say we didn’t fish again for the rest of the crossing. There was enough food on board as it was.

After leaving the continental shelf we didn’t see any other boats except for one night when I spotted the lights of a ship in the distance. The AIS informed me that it was a Navy Hospital ship. I didn’t believe it but decided not to take aggressive action just in case.

We did see one other boat the night before arriving in Hawaii. We came within a mile of the Enchantress, another small sailboat who happened to be an equal 24 days out from California. We spoke to the captain on VHF and informed him of our similar plans to wait out the night before making landfall in Hilo.

Land hooooooooo!

The next day the volcanoes of the Big Island appeared from behind the clouds. Wow. At the same time the trade winds disappeared. We spent the whole morning slowly beating into light winds before we were able to enter into Hilo Harbour. I hopped off onto the SUP while Dave decided where to drop the hook. The smell of land was bizarre and comforting. What a feeling.

The moment I stepped on shore that night I felt an energy like no other I had ever felt in my life. I fell in love with Hawaii instantly.

Dave, Dolce, and I had just sailed over 2300 miles in 25 days from San Francisco to Hilo, Hawaii. I was super stoked, but... the previous night I had woken from a bad dream that was soon to play out in my waking life.