For every offshore passage, there’s a little series of ‘X’s on the chart that lead out into an expanse of blue and the realization that the boat is now hundreds of miles from land.

In sailing, and in life, there are rites of passage. I learned to sail a rather unorthodox way: right after purchasing a 34-foot sailboat, Force Five, with my boyfriend Curtis while on the island of Saint Martin. We had flown to the island with two very large bags each, filled with enough clothes, tools, and books to get us started on an anticipated two-year cruise. Curt had been sailing since he was kid. I had virtually no sailing experience. We had known each other four months. I had taken a leap of faith that we were about to embark on a life-changing adventure and that along the way I would learn to sail and manage the boat as we moved from one exotic destination to the next. For me, returning to Saint Martin after eight months of cruising culminating in a five-day trip from Venezuela felt like a big rite of passage in my sailing career.

And I did learn to sail along the way, but it was a bumpy road. I am jealous of those people who have the comfort of becoming accustomed to the heeling of the boat without the sound of their dishes crashing to starboard in a gust of wind. I am envious of those who get to grab the wheel when it’s time for a “lesson” instead of having to take over when a shackle breaks from an accidental jibe and the skipper needs you to steer in heavy weather while he repairs the damage. And it’s always nice to be able to choose the weather you set out in, rather than have a place you have to depart for and learn by way of baptism by fire.

After nearly eight months, 24 islands, and over 800 miles, we had reached Venezuela and I had started to feel like I had the hang of this sailing thing. By the time our friends had booked their flights to Saint Martin for Christmas, I felt that I would be able to tell them that I actually knew how to sail. The downside was that the holidays were so close, and Saint Martin so far upwind, that we had prevented ourselves from island hopping our way back up to meet them. We were going to have to make the trip in one long passage. To complicate things further, as we waited in Margarita for a weather window to make the five-day trip, we had run out of time. The day came where we had to leave regardless of what the weather had to say about it.

We set sail with the rising sun: the forecast was for 25 knots from the northeast and eight foot seas. Our destination being due north, we planned to try to follow the curve of the island chain to the northeast as much as the wind would allow us. I stared at the chart showing the rhumb line that would take us 100 miles from the nearest land.

The first few hours out we were lively, with gray skies densely streaked with clouds. Our first day passed, uneventfully but busy in its own way. The fast winds made for fast sailing and we were making great time. At nightfall Curt and I settled into the pattern of our watch schedule. He'd start with 18:00 to 21:00, and then I'd take 21:00 to 0:00, he'd be on from 0:00 to 03:00, and so on.

This was the trip that Curt started calling me “Nav,” short for Navigator. I found that I developed a compulsive habit of taking our latitude and longitude down on the chart almost hourly and checking in with other boats on the SSB radio whenever possible. The “X” marks that identified our location were increasingly further from the nearest land. Inevitably, I had kept an informal tally of how long it would be before we could get to land again if something were to happen.

There are lessons learned the easy way, and then there are lessons learned the hard way. A sailor assesses a blown out main.

I don’t sleep well when we're underway, and that first night was no different. As we pushed onward as straight into the winds and seas as possible, our boat sounded like she was about to break up under the beating of the crashing waves. Below, it was impossible to move without grasping a handrail or a table to move about. The boat felt like she was like a rock skipping on a river. But when my turn to keep watch came, I recall feeling oddly confident. Curt apprised me of where we were, and passed me a flashlight and GPS. He went to bed, and there I was: just me, our boat, and the open ocean.

The moon had been growing for many days now, and while it wasn’t full, it was bright. The nighttime world around me had that surreal quality like I was living in a black and white movie. I sat in the cockpit trying to dodge the waves that were crashing into the cockpit. I was soaked and getting bitter. The upside to the waves was that I didn't have to struggle to stay awake that first watch.

When Curt returned three hours later for his turn, I went below and tried once again unsuccessfully to sleep. I was unnerved listening to our anchor banging out on the bow. We had lashed it down, but from below it sounded like it had come loose and was bashing away at the hull. I mentioned it to Curt, and he'd tried to spot it from the cockpit with his flashlight. It seemed fine from his vantage point, but as the sun rose, we saw that it had actually torn loose and was rumbling about. Force Five was climbing and launching off each wave and the winds were howling -- hurling us along -- all the more reason we needed to get the anchor stabilized. Someone had to go up to the front of the boat and tie it down again. We decided it should be Curt, and I would steer the boat.

One of the sailing lessons I hadn’t learned up to this point was heaving to: a process whereby one stops the boat from moving forward by setting the sails in a particular manner and steering into the wind. I had read how to do it, but never actually done so; neither had Curt. I suggested we take a minute to look this up in some book before we tried to actually do it. The anchor had been loose for hours now, and I didn’t think a few more minutes would hurt. Curt vehemently disagreed. I rebutted. He told me to just turn the wheel to the right and hold it there. I asked if this would just turn us in circles, and he snapped at me to just do it. He had clipped into the jack lines and was already making his way towards the bow.

I was fuming. I clenched my jaw shut, no matter how hard I wanted to stop him. We had agreed that in situations like this we would talk it through before we executed it and this methodology had served us well in many situations. Now, over a hundred miles away from land, didn’t seem like a good time to be breaking our agreement. Curt had said to steer right, and hold it right. I bit my lip and did it.

I thought, “This can’t be right.” The boat would climb a wave, stall as we faced dead into the wind and then whip around violently as we careened down the other side of the wave and caught the wind in our sails again. The boom would crash jibe across the boat, shaking the boat to the core. Curt was hanging on at the bow trying to fix the anchor. I yelled forward, “This can’t be right! Is this what you want?” First he ignored me completely, then he brushed me off with an arm gesture. “Curt! Do you see this?” He ignored me still. I continued to hold the wheel. In my head I was telling myself to trust him. This is what he said to do and I'll just shut up and do it. I was still so mad I couldn't see straight. I was mad for not talking about it first. I was mad for not being heard when I disagreed with him. I was mad for being ignored. And more than anything, I was mad for seriously putting both the boat and us in this situation and not thinking it through first. Each turn -- climbing the wave, stalling, careening down the other side, and then the subsequent crash jibe shuddering the boat from mast to keel -- made me clinch my jaw tighter. I gripped the helm harder and told myself over and over to keep my mouth closed. When he crawled back from the bow it took everything I had to try to control myself.

“Was that what you wanted to happen? I held it right like you asked, but surely that wasn't what you wanted to have happen?”

“I guess our boat doesn't heave to the way other boats do.”

“Have you ever even heaved to before?”

Force Five on the final stretch for Saint Martin after five days at sea.

A strained "conversation" ensued. I tried to say my peace. “Can we please just take a second to talk about things next time? The only time things go wrong is when we don't talk things through first.” He felt we didn't have time. It needed to be done right then. And I know the rules: you listen, and do unequivocally what the Captain says. I was calculating my rebuttal when he looked up and stated quite plainly that the mainsail was ripped. I thought he was kidding and stared at him for a second before I realized he wasn't. I looked up at the sail. A tear ran just below the third reefing points from the leech about half way towards the mast. I thought to myself “See!” but didn't say it. We had more problems to deal with now.

The conversation came to an abrupt halt while we faced the next crisis. For a moment we just stared at the tear. I did the quick calculations about how far away from land we were. Already, it would be a day or two before we could make landfall. Not that this was necessary at this point. How can we make use of that sail now? I offered to try to sew it. I had seen sail repair instructions in one of our books. Curt reviewed what other sails we have below. We decided to try to take the sail down to the third reef and lash the torn bottom half to the boom to minimize further damage. Given that the conditions hadn’t lightened, we still had enough wind to sail. With the sail reefed, we were still careening along at 6.5 knots.

We each sat there in silence staring at the sea ahead. There was no reason to get into the events of the morning anymore. We returned to our watches and kept going. We had at least three and half more days at sea. The boat was handling fine, the wind and seas continued to be strong, and even with the third reef we were making good time. Perhaps tearing the sail had prevented some other disaster we are lucky enough to have never seen. We always try to look at things that way.

And so the days passed: one watch into another, and another. On the fourth day, the winds finally relented to 15 knots. As I marked our bearings the little "X"s drew us closer to Saint Martin slowly, but surely. Finally, Saint Martin was in our crosshairs on the horizon. We thought we could make the 17:30 drawbridge opening, but of course, now the winds had died and we seemed to be moving at a snail's pace. While we waited to get there, we had time for reflection. The sun was setting low in the sky, casting brilliant white light on everything and long shadows in the wake of the sun's rays. It was the time of day when over the past five days we had opened a bottle of wine before resuming our night watch schedules, and prepared for nightfall by donning our sailing harnesses and foul weather gear. Tonight however, Curt sat on the deck leaning forward with his elbows on his knees staring at the island in the distance. It was the perfect afternoon for us to return to what we think of as our Caribbean home. I joined him on the deck.

“What're you thinking about?” I asked.

"I don't know. Everything. It feels like we're coming full circle."