05/01/2015 04:50 pm ET Updated Dec 06, 2017

How Does It Feel to Sail Across an Ocean for the First Time?

How does it feel to cross an ocean with a sailboat for the first time?: originally appeared on Quora: The best answer to any question. Ask a question, get a great answer. Learn from experts and access insider knowledge. You can follow Quora on Twitter, Facebook, and Google+.

Answer by John Friend, CTO, multiple startup guy, sailor

Image by Tiago Fioreze

I sailed from California to Hawaii twice when I was a teenager, once with my Dad on a 25' sailboat and once as the navigator for an elderly couple that was planning on retiring to a sailboat and sailing all over the world.

The first time you make a major ocean crossing is definitely a unique experience. You head out to sea and within hours, you watch the coastline disappear and all of a sudden you're completely alone.

You put your faith in your compass and navigation instruments that you'll actually end up where you plan to end up in some number of days or weeks later. In my day, we were using celestial navigation (combine the exact measurement of sun/star angles with an accurate time source and then do a bunch of table lookups in navigation tables). Nowadays, you presumably just use handheld GPS (not quite the same feeling probably).

The mind can't help wondering about the dangers of the trip. When it gets windy in a sailboat and the boat starts to accelerate, you can hear all sorts of noises. Some of the noises are just the passage of the water and waves. But some of the noises are groans and strains from the rigging, keel, hull, and rudder. In our boat, if you picked up a cover on the floorboard and looked at the hull and keel, you could literally see the hull and keel flexing. That's actually normal for fiberglass, but it gets your mind thinking. If the boat gets severely damaged and you're forced to leave it, you are at the mercy of a life raft and some kind of rescue. Could you get in the raft in time (what if you were asleep)? Would you have enough supplies to survive until rescued? Hopefully you do your planning for that possibility before you leave and then, when you think about it on the trip, you feel like you've done your preparation so you should be OK. But, when you hear some unfamiliar noises coming from the boat, you start to wonder again.

On the way to Hawaii in a relatively small boat, the first few nights are kind of rough. Besides the fact that you're not that used to the daily routine, the weather right off the California coast is not that warm. For us, it was quite windy and the wind wasn't a particularly favorable direction -- we called it the California nasties. Later on in the trip, the wind gets more behind you (making for a smoother ride) and as you get closer to the tropics it gets a lot warmer (downright pleasant). I remember one particularly windy night only a few days into the trip. It's pitch black. The wind has increased in the last few hours and we decide we need to change head sails and put up a smaller jib. As we plunge off each wave, a shower of spray goes across the deck. Lots of our clothes are already wet and it seems like nothing will dry (high humidity, not that warm, salt encrusted). It's my job to go on deck. I consider my clothing options. I can put on multiple layers of clothes under my foul weather gear, but there's so much spray that it's not really going to keep me that dry. Or, I'm thinking to myself, I can strip down to just my swimsuit, endure the cold spray for the short duration of the sail changing job and keep my few currently dry clothes dry. I go for the swimsuit and it turns out to be the right call. The spray was cold, but my clothes and gear stayed down below and dry.

During the trip, there was both plenty of free time (I played my guitar and read several books) and plenty of things to do. With only two of us on my first trip, we had 4 hour watches. 4 hours on, 4 hours off. Your 4 hours on consisted of regular checks of the weather conditions, the course, the boat's equipment, sail and steering adjustments, the marine traffic in the area (if any) and sometimes navigation. We had a home-built self steering system so you didn't need to steer all the time, though you could take over and steer manually if you wanted to. You had some free time during your watch, but you couldn't get too engrossed in any activity because there were plenty of things to be regularly vigilant about. You would spend most your off-watch time trying to catch up on sleep. The body doesn't really like getting sleep in 3-1/2 hour increments and I was pretty much always tired. I imagine that a body can get better adjusted to sleeping in multiple shorter increments with practice, but my body wasn't adjusted to that. Even your 4 hour off-watch time period might get interrupted by an event on the sailboat. If a sail change was needed, we had a policy on the boat that both people had to be awake for any activity on deck (out of the cockpit). That was mostly because we wanted the other person awake and alert and watching in case someone fell overboard or got injured. Fortunately, I was usually so tired when it was my turn to sleep that it really didn't matter that the boat was rolling and crashing into waves. I always felt like some part of my subconscious was paying attention to what was happening in the boat even while I was sleeping.

Falling overboard was the biggest daily risk, and I spent a fair amount of time thinking about. If you were on a solo watch (the other person was sleeping) and you fell overboard, that was probably it for you. The boat's self steering system would just keep driving the boat for hours until the other person awoke and found you missing. Turning the boat around and retracing your path to try to find someone who had fallen overboard would be like looking for a needle in a haystack. From the low angle of the cockpit of a 25' sailboat, it's virtually impossible to see a person in the water among the waves unless they are very, very close. They could be 100' away, able to see the mast of the sailboat, but you couldn't see or hear them among the waves and the noises of a moving sailboat.

To alleviate the risk of falling overboard at any time, we had a rule that if you ever went up on deck (out of the cockpit) when the other person was not also out in the cockpit and watching, you had to wear a two clip safety harness that was always attached to something sturdy so if you fell, you would still be attached to the boat. The harness made moving around a lot more time consuming, but it did assure you weren't going to get separated from the boat.

In between all your regular responsibilities, there were plenty of great times on the trip. One day we discovered there were pilot fish swimming along with our boat. If you looked down by the rudder, we could see these fish swimming right next to the rudder. I've been told that they're using the boat as protection from predators. I don't know if the same fish swam with us for much of the trip or if they'd join us for awhile and then drop off only to be replaced by others, but there were nearly always fish there. On another day, we saw whales swimming along in our direction, about 50' off the beam. As we sat on deck watching, they did their classic tail-up dive and disappeared. Just as we were about to give up watching for them to surface again, one whale came up and did a giant breach, coming at least half way out of the water and landing in a big splash. If you've never seen something like that, it's quite a spectacle.

Another morning, as the sky lightened with day break, we discovered all sorts of small flying fish stranded in our cockpit. As we looked around, every time a wave would crest, we'd see hundreds of flying fish skimming along the surface. By poor luck, some of them would end up in the cockpit or on deck.

As we regularly had little rain squalls going through, there was no shortage of interesting clouds, interesting lighting and often beautiful sunrises and sunsets (and someone was always awake to see them).

So ... you go days and days (in our case two weeks) without seeing land. You would occasionally see some other signs of life (ships or other sailboats, but not very often). Your navigation says you should be coming upon the Hawaiian Islands soon. We were approaching Kauai with its 5243' high mountain. You start to wonder if all this navigation stuff has really worked. Are we going to find the island? What if we're systematically off by 100 miles and we miss it? Several times a day, you calculate how far away the island is and you really begin to wonder how far away you should be able to see a 5000' mountain.

At 100 miles from where we think the island is, we can't see it. The sun is getting low and it's starting to get darker. There have been rain showers on/off affecting visibility. Finally, at about 5pm, a rain shower clears and we can see the mountains on the island. Lo and behold, it is right where it's supposed to be!

After a brief celebration, we start to discuss plans for getting ashore. Unfortunately for us, it's getting dark and we don't feel like we can arrive in a strange location in the dark and safely avoid reefs and breaking waves. We were aiming for Hanalei Bay and planning to just anchor in the bay and row our inflatable raft ashore, but there's no lighted marina with navigation buoys to direct the way. So, at 6pm, we decide that we can't land tonight. We'll have to wait off the coast until morning and go into the bay at first light. We turn around and head a little further out to sea to a safer distance from the island and any shipping traffic around the island.

When we're comfortable with our position, we "heave-to". This is a sailing maneuver where you put up a smaller jib and you backfill the jib. It holds the boat in a relatively stable position to the wind, kills your forward speed and the boat just very slowly drifts sideways downwind. It's a means of keeping the boat relatively stable while not moving very much.

This was the longest night of the trip. With the currents and wind and darkness, we weren't particularly sure how fast the boat would drift and the heaved-to motion was very different from what we were used to while actively sailing the previous couple weeks. There were some rain showers on/off a few times. The darkness seemed a lot less friendly knowing there was an island nearby and possibly other boat traffic.

Finally dawn arrived. The island was still where we thought it should be. We charted a course for the entrance to Hanalei Bay and entered it without any difficulty. We dropped anchor, inflated the raft and rowed ashore. I remember climbing out of the raft and putting my feet down on the beach sand. I stood for a moment and the beach felt like it was moving and I lost my balance and fell over. As it turns out, my inner ear was so adjusted to the moving platform of a sailboat that when I stood on the beach and the beach wasn't moving my balance was completely fooled. It had forgotten how to handle the steady ground. We laughed a bit, sat on the beach for awhile and got used to it.

In a complete stroke of luck, the rest of my family had arrived at Hanalei Bay (by airplane and car) the day before. The transit time of an ocean crossing in a sailboat is anything but an exact science, but my dad's estimate for how long it would take us to get there was within a day and the rest of the family was waiting there for us.

I kept a daily journal during this first trip, and even now 36 years later, it's fun to read through the journal. I wrote a college application essay on the experience of seeing the sun rise on the open ocean at the end of your solo 4 hour watch and that essay helped get me into Stanford.

There's no question that it was an amazing experience for me. I owe my Dad a lot of thanks for planning this extraordinary trip and making me a part of it. We had a unique relationship on the trip. I knew that he was ultimately in charge, but he treated me like an equal and when there were decisions to be made, we discussed the options together and decided together. If we had differing opinions, sometimes we'd go with his idea, sometimes with mine. That was a big deal to me as a 17 year old.

In an effort to do something along these same lines with my own 16 year old son, we climbed Mt. Whitney together a couple summers ago. We spent six months training for and planning the trip, spent days at altitude acclimating to moderate altitude, backpacked up to 12,000' and then ascended Mt. Whitney (14,505 ft). Though many more people a day make it to the top of Mt. Whitney than sail across an ocean, hopefully my son felt some of the same experiences I did on my sailing trip. Incidentally, he wrote a college application essay about his Mt. Whitney trip (still waiting on college acceptance letters).

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