Sailing Across An Ocean Will Change Your Life — Here’s What To Know Before You Go

I remember the first conversation I ever had with Anna. We were sitting in a wood-paneled teacher’s lounge in Moscow, and everyone was telling stories about what brought them to Russia. I said that I was there because I’d studied the country’s history. Anna was there to travel. We both wanted to take the Trans-Mongolian Railway to Beijing when our contracts were up. It was one of those conversations that you have a million times. They seem inconsequential… until they don’t. That little bit of idle chit-chat changed the course of both our lives.

Six-months later, we were engaged and living in Phuket, Thailand (after having taken the Trans-Mongolian Railway as a couple). We’d found a brand new apartment building just outside of Phuket City — it was empty except for us. About two months before we arrived, a tsunami hit Thailand, devastating the local economy. We found ourselves living in a village brimming with out-of-work chefs from all the resorts in the area. Every night we’d stroll the main drag — inhaling the smells of frying chilis and fresh basil and listening to the buzz of passing tuk-tuks. Over and over we were treated to food from some of the best chefs in the country, who had little choice but to set up shop on the roadside to try and make ends meet. We shared Thai whiskey with them and they shared the secrets of the wok with us.

Trying to find a job in post-tsunami Thailand was tough. Many of the ex-pats had moved on. Tourism was at an all time low. We’d gone to support the economy, but didn’t have the money to loaf forever; teaching opportunities were scarce. After about two months without work, serendipity struck. While sitting at a burger bar in Chalong Bay, Anna and I were having one of those not-so-pleasant conversations about running out of money. We both had differing opinions about the way to move forward. Then I spotted a xeroxed 8×11 on the beer refrigerator next to the bar:




I jumped up and grabbed the flyer. I showed it to Anna. She looked it over and dropped it on the table. She looked at me like I’d gone mad.

“What exactly are we supposed to do with this?”

“Call him! Let’s get the job!” I said.

“I don’t know anything about sailing. I’ve never even been on a sailboat.”

“It’s not that hard! You can learn as you go.”

“It’s sailing across AN OCEAN.”

“I grew up on a boat, practically. It’ll be — ”

“No,” Anna said.

Her tone dealt an uppercut to the conversation. We ate our cheeseburgers and drank our Chang Beer in silence. The bartender took away our empty plates and brought back two more beers.

“So…?” I tried again after a few minutes.

“WHY…WOULD…I…CALL?” Anna said, exasperated. “They aren’t going to hire me to crew a sailboat when I’ve never sailed in my life!”

“Everyone learns to sail by actually sailing. It’s the boredom that you have most to worry about. The rest is easy!”

“What if there’s a storm? I have no idea how to handle that.”

“Hey, if something is going to happen, it’s going to happen out there…not sitting here.”

I’d just quoted Captain Ron to my future wife.


“Call him!”

More glaring silence. A few days passed with no job offers, a few nights passed drinking Thai whiskey on the stoop of a 7-Eleven. Finally, I was able to convince Anna that we should at least meet these people and see what the sailing opportunity was all about. I’d like to say it was my great oratory skills that finally convinced her. But it was more likely the heady confidence that comes with drinking Mekong Whisky in 100% humidity.

To Anna’s shock, we landed the job. The captain agreed with me, you can learn as you go. He was an American, sailing his family around the globe over a two year stretch. His wife had broken her foot when they arrived in Phuket and was going to stay in Thailand for surgery. Their 12-year-old daughter would hang back to keep her company. The captain and his son would press on to Europe. They just needed some crew to make up for the missing wife and daughter.

It’s crazy to consider how much of a role chance has in our lives. We were in a random burger bar. Meanwhile, a random person we’d never heard of breaks her foot. Next thing you know, we’re sailing across the Indian Ocean on a 54-foot sloop with three people we’d barely met. Life…

Along the way, we did indeed learn an immense amount. So if you’re dreaming of embarking on a similar adventure, here are a few things to consider:


The first night on the boat, Anna and I closed the door to the forward cabin, where we were to stay. That door stayed closed for about an hour. It was just too hot and muggy. At 54 feet long and 16 feet at the beam, the sloop was not exactly spacious. Our bathroom was the size of a airplane lavatory with a tiny shower (more on that later) that four people shared. There was a nice salon with a kitchen. But, again, it was way too hot to stay below deck. The majority of the time we spent topside with everyone else. There really isn’t any place to hide on a boat. So you need to be really affable. Our first passage from Thailand to the Maldives was 18 days of sailing. Think long and hard if you can stay cooped up for damn near three weeks with anyone. Some passages across the Pacific reach into the 30 day range. Your need for privacy erodes at a pretty fast clip.


I’m not saying you need to be in peak physical condition to sail. Most old salts are a swig of rum away from death. However, your body is going to be working the whole time. On our first passage, 16 of those 18 days were spent beating. That means we were sailing into the wind, shifting the bow at a 45 degree angle. You are basically making a zig zag. We’d turn every few hundred meters on a hard day. We were basically racing to catch the tail end of the western Indian Ocean trades that help you coast towards Africa. The wind was against us for the first sixteen days. Your muscles start to wear down. You sleep against a wall and then are thrown into the opposite wall when the ship tacks left or right at 45 degrees. Imagine living for over two weeks on a 30-45 degree angle with water and wind spitting in your face.

4 – FOOD

Our captain was an old-school dude. He wholeheartedly believed that while at sea you should make every dinner a little special to keep up morale. It 100% worked. Generally, we’d fend for ourselves for breakfast and lunch, then we’d rotate who cooked dinner/did the dishes every night. The fun part was cooking in a kitchen that has a floating stove while beating and jibbing against the wind and trying not to let the pot of boiling food spill all over yourself. The next time you’re in your kitchen, image if everything was constantly moving. Or, just have your partner come in and constantly move things around and periodically shake you the whole time and throw you into cabinets. Sounds fun, right?

That being said, make sure you have nutritious staples. Catch fresh fish to bolster your fat and protein intake. And avoid alcohol at all costs. You do not want to further dehydrate yourself (yet further proof that pirates were tougher than the rest of us).


Sailing allows you to go places that a lot of tourists aren’t really allowed. In the Maldives, for instance, there are a ton of islands and atolls that are off limits unless you’re in a sailing yacht. So you’ll have access to places that have zero tourists. Moreover, if you do get stuck out in the sea, almost every country has to allow you a safe harbor. We were able to go to Oman without visas because we needed to refuel after losing the wind in the Arabian Sea. By coming into ports of call, you get to see sides of countries that you’d generally never see as a tourist, or a traveler. That’s always cool. The island in the photo below is a tiny village that makes up Hoarafushi Island. They have you check in when you arrive by signing into their ledger (which went back to the early 1960s). We were first boat there in a year, making us the 127th vessel to arrive on the island since the early 1960s. No one else had been there. That’s special.


Fresh water is a highly-prized commodity aboard a ship. We basically all skipped showers so that Anna, the only woman aboard, could have a fresh water supply. That meant sailing through rain, getting out the soap and hoping you could rinse off before it stopped. Or, using Sauve (it lathers in salt water) and pumping sea water on deck. Or just grabbing a rope and jumping off the stern into the sea and being dragged for a while. The friction cleaned everything. Sharks be damned! If you’re sailing anywhere near the equator, you’re going to be constantly sweating. Salt water baths are a must. Luckily the water is generally bath water warm in that part of the world. So that’s a plus. I can tell you when we arrived in Djibouti and checked into our hotel, I took the longest shower of my life.


This is by far the hardest aspect of sailing to overcome. We crewed in four hour shifts. I had the graveyard shift when everyone else was asleep and the world around me was pitch black. The first few days, you stare at the stars for an hour, maybe more. Then you spend days fighting sleep. Being that it’s night, you need to stay fairly focused on the radar as those are your only eyes. Then, just when the boredom seems to be unbearable, you remember there are stars! That works for another hour or so. You get the point.

You’re also dealing with the everyday monotony. There are only so many conversations to be had. We’d scour books for new card games to play. I must have read 30 books in three months. Seriously. I don’t think I read a book for a year after that trip. You start to have really petty and pointless arguments. The captain and I argued for an hour (AN HOUR) once about a rule in Risk. But, it being a boat, once it’s over, it’s over. We got on like it never happened. Because you have to. You start filling your time with push up contests, fishing, writing, taking stupid photos, anything. And you still have so much time to just sit and stare into the blue. Or, in my case, the darkness.

So, if you’re thinking of taking the plunge and sailing the globe, keep the above in mind. What’s crazy is that all of that sounds terrible now, but sailing is probably the most rewarding and fulfilling way to travel. I can’t wait to get back on the water.

Anna and I stayed together after being confined together for three months at sea. Spending that amount of time with someone is a trial. There’s nowhere to hide. It proved we could handle anything. And, so far, we have.

Plus, she kicked ass as a sailor.