A Day In The Life Of A Wannabe Sailor

Whenever you do something outside of the local “norm,” you’ll inevitably get peppered with questions. And although the questions might seem basic, there’s a reason behind them. Which is why I’m writing about a day in the life of a wannabe sailor.

I just spent a week learning to sail a sailboat. When I started telling people about it, they always seemed confused. What exactly was I going to be doing? Where would I sleep? What do you mean, learning to sail? Are you going to be in a classroom?

Fair questions, even if some of them were spat at me, accompanied by a look of disbelief and skepticism.

I didn’t let them sway my decision to continue with my dream of learning to sail.

(Not that changing my mind would have done any good…as the deposit was non-refundable.)

But I digress. Let me paint you a picture of what a day in the life of a wannabe sailor looked like, according to my personal experience!


Actually, before I start I need to throw a little caveat out here. Each day was different, but had a similar layout. When you’re learning how to sail, there are so many skills, drills, and techniques that need to be practiced, with a limited amount of time to do so.

A DAY IN THE LIFE OF A WANNABE SAILOR: MORNING

6:30-8am: Wake up

I was usually the first person up in the mornings. I wake up with the sun, even though I was in another time zone and we experienced daylight savings time during the week.

First order of business was getting outside and taking a few moments to myself. Smelling the salty air, often mixed with diesel exhaust, sunscreen, and leftovers. I would use this time to take some pictures of the boat and our surroundings, before the rest of the world woke up.

I would also use this time to meditate, journal, and just simply enjoy our surroundings while I seemingly had the saloon and cockpit to myself.

8am: Breakfast

Usually by 8am, I was no longer enjoying the solitude that the early hours often afford, but it wasn’t necessarily a bad thing. The boat began to wake up and either myself or Jack, another student, would start breakfast.

We ate well on the boat, as you’ll learn. Breakfast included scrambled eggs, french toast, bacon, fruit, bagels, and omelettes.

The noises and smells associated with cooking were usually enough to get all of us students out of our cabins and into the saloon.

We generally ate all of our meals together around the table in the saloon or in the cockpit, based on whether or not we were also studying…

9am: Studying/testing

Once we were all fed and the others caffeinated with their coffee (I was off soda for the week, believe it or not), we cracked open our textbooks and spent the next hour studying for the next exam.

We were all going for the same certificates, so we were able to quiz each other, ask questions and discuss the things we needed to know together. It was a unique bonding opportunity.

After we felt ready, we would grab our notebooks and take our test…usually all before our captain would emerge from her cabin. I’m not sure if she’d had a group that was so proactive before, but it was always gratifying to see the sparkle in her eye as we told her we were done with the exam.

A DAY IN THE LIFE OF A WANNABE SAILOR - open 3 ring binder with a test open and pencil laying on it

10:30am: Cleaning up/getting ready for the day

Once we were finished with our exams and breakfast, we’d spend the next bit of time cleaning up: dishes, putting food away, putting away any clutter that had accumulated, and pulling in anything that was left on deck.

This was also the time that we’d get changed, put on our sunblock and sailing gloves, and filled up our water bottles. Getting ready for the day was paramount, since we never knew what we were really in store for.

A DAY IN THE LIFE OF A WANNABE SAILOR: AFTERNOON

11:30am: Sailing

This is where the days varied greatly for us. We had a number of skills that we needed to learn, all while navigating the boat from one location to the other.

Some days we practiced tying knots.

Other days were spent docking and pulling away from the dock.

Every day we had a turn at the helm, using the power of the wind to sail towards our destination.

And every day we practiced tacking and gybing – techniques you use when you want to turn the boat, by moving the sails from one side to the other.

Each day was packed with emotions, knowledge, and adventure.

All 4 of us students had our own reasons for wanting to learn how to sail, and were thus motivated to do our best. We offered tips to each other, discussed any “problems” that arose (like a block blowing off of the starboard deckhouse – yikes!), and fell into an almost-routine of our preferred stations/jobs.

I was usually found on the port side to handle the port jib sheet and port main sheet, with easy and quick access to the main halyard to raise the mainsail.

During stretches of calm where the wind was good and steady, and no sail changes were needed, we’d usually congregate at the helm where our captain usually was located. We’d receive instruction and just listen to basically whatever she had to say. She was extremely knowledgable and experienced, so hanging on her every word was always a great learning experience for us.

While sailing from one place to the other, we’d spend time plotting out our course. Although it would look like a straight shot to our intended heading, we’d inevitably need to perform some sail changes.

We got to the level of proficiency where our captain would essentially allow us full control to choose where to make sail changes. I can’t tell you how empowering that was.

Although we were running drills and learning techniques, our captain had a way of making it more than…basic.

For example: on our first day of sailing, we had a buddy boat with us. The buddy boat was a larger catamaran from our sailing school, that also had 4 students and an instructor. One of the first things you learn to do on a sailboat is how to make it move. In order to do that, you need to learn how to harness the power of the wind by using the sails. We needed to practice how to tack and gybe.

Instead of just rotating between the 2 actions, we essentially played a “war game” with our buddy boat, almost like Battleship. Each sailboat tried to get as close to the other as possible and “attack” the other using…GRAPES!

We were constantly circling each other, getting as close as possible (but not too close, since we were sailing and needed to maintain control). Each time we’d pass the other boat, our captain would yell out a command: TACK! GYBE! TACK!

And then we’d hear: PREPARE TO FIRE! While trying to still hold onto the boat, perform our duties, we’d be digging in our pockets for the grape ammunition we’d stowed away.

When we finally would get close enough to fire, it was always a crap-shoot because the grapes had squished and we were wearing sailing gloves. Picture throwing a super small baseball while wearing thick batting gloves.

Oh, and it was raining and the seas were gnarly. So we were also hanging on for deal life on the sides of the boat.

A DAY IN THE LIFE OF A WANNABE SAILOR: EVENING

5:30pm: Arriving at a New Location

One of the benefits of having your sailing school on a live-aboard boat is that you get to travel to a variety of locations. Every night, we slept in a new location and practiced mooring, dropping the anchor and docking.

First order of business was to secure the boat to make sure it didn’t go anywhere.

6:30-8pm: Dinner

If you’ve been paying attention, you noticed that there wasn’t a “lunchtime” section in this day in the life of a wannabe sailor. No, I didn’t leave it out. We literally had lunch on the first day only (because we prepped wraps before leaving the marina), and snacked every other day.

When you’re out sailing and working, time just flies by.

So as a result, dinnertime was super important. And again, we ate well.

I loved cooking and tried to do the majority of it, mainly because I didn’t want to clean. It worked out well for us, as one of the other students preferred to clean up. Win-win.

Cooking in a galley on a 37-foot catamaran takes some getting used to. Not only is your space limited, but your cooking surfaces are significantly tighter than what most land-lubbers are used to.

We usually took at least an hour to prepare dinner – mainly because we also had limited preparation dishes. Once something was made, we had to quickly wash out the mixing bowl so it could be used elsewhere.

And then after dinner we would just talk about the day, enjoy where we were at, chat about what was to come the next day, and recount any significant moments.

Our meals included BBQ chicken on the grill (which we attached into a fitting on the stern/back of the boat), burgers, shrimp and scallop pasta, fish tacos, all types of salads and dips, and fruit.

8pm: Clean up dinner

In order to conserve water, we learned to dip the dishes and plates into the ocean since we were far enough away form the shore. No, we didn’t have a dishwasher on the boat, but since I usually cooked, I was spared from KP duty. Although I did help put dishes and food away, and helped clear dinner items.

9pm: Study and Review Previous Test

After dinner, we’d sit around and study. Again. Literally, any chance we had, we’d study and pepper our captain with questions. Thankfully it paid off and I passed all of my exams.

10pm: Prepare for Bed

After a full day of being out in the sun, working hard and playing hard, the end of the night was a welcome reward. We each had our own cabin with a queen-sized bed, with a shared head between the 2 cabins on each end.

My typical preparation for bed included brushing my teeth, using baby wipes to get as much dirt, sweat, and sunscreen residue off of my body, turning on my fans and then just laying there until my body cooled off enough to think about falling asleep. It never took long to actually pass out, thankfully.


Well there you have it! That was a “typical” day in the life of a wannabe sailor. Obviously there were variations, but structurally we followed the same schedule-ish.

And I loved every minute of it.


Have you ever thought about going to sailing school? Would you last a day in the life of a wannabe sailor?

Sharing is caring! Please show some love by sharing on PinterestFacebook or Instagram! Thank you!


PIN ME