It just has to be called a “shakedown” cruise. If the boat was in storage for only a few months, we could just call it a “continuation”. But no, at two and a half years, it has to be called a “shakedown”.

And for my shakedown, I chose 325 miles through the Caribbean Sea, from St. Kitts to Grenada. How bad could it be?

“There is nothing more enticing, disenchanting, and enslaving than the life at sea.” – Joseph Conrad

Within minutes of leaving the boatyard I had all three sails up, the rigging straightened out, and making good headway south-southeast.

Unfortunately, my self-steering Cape Horn wind vane wasn’t working. The steering quadrant just wanted to flop over to one side and not control the rudder.

Great, I better get this thing working because I am not steering by hand for 325 miles!

So in the meantime I was able to get the sails trimmed and balanced just right. I figured out the appropriate combination of reefing & sail selection to get the boat in the sweet spot where she’d sail without me touching the tiller much at all. Happy day, figured that shit out right away! Like riding a bike.

I couldn’t bring myself to go down below for much longer that a few minutes at a time. Secretly, it was seasickness, but as far as you’re concerned I just didn’t have my sea legs back yet. So I skipped dinner and just snacked the first night.

It had taken me months to get brave enough to sleep in my boat alone while she kept sailing through the ocean. Once I accepted the fact that, hey idiot, you’re only covering one mile about every 10-15 minutes, it’s fine to take a half-hour nap. This was a tough transition because in my previous life I’d cover one mile in about 5-7 seconds.

Believe it or not, my first night back out I was actually able to nap in the cockpit! (Still just not down below – you know, the sea legs thing). This was good to know. I tied off the tiller and trimmed the mainsail for a bit of weather helm so that if the winds picked up while I was sleeping, we’d round up into the wind instead of getting knocked over.

The first night was a pleasant mix of looking at the backs of my eyelids and looking at the stars (all of them). I hope you enjoyed the first night because it only sucks from here…

Winds really started to pick up the second day. I did manage to cook myself a breakfast of scrambled eggs, onion, and potatoes. The sun was out, the seas were pleasant, and I was back at the helm in Saoirse sailing to Grenada. In the afternoon I had to reef the jib. We were heeled over quite a bit and I had to reduce some sail.

I loosened the sheets, dropped the halyard, and went up front to take the sail down. But before I took the sail completely down, I wanted to make sure I had the correct reef points identified. So the upper part of the sail was flapping around while I inspected the lower part. I started the reef and while I was almost finished tying it all off, noticed something I didn’t want to see.

A strip of the reinforced part of the leech (back of the sail) ripped from the rest of the sail. Dammit.

I tied the jib off to the starboard side lower lifeline to keep it out of the way and raised the staysail. Fortunately, with the winds we were in, I was still able to almost keep the same speed and same balance with a reefed mainsail and full staysail. I didn’t really want to repair a sail at sea if I didn’t have to, so I was glad the staysail filled in for the jib/job (I didn’t know which word you’d think was a typo).

Ok, back at it! No naps this day, had a tiny bit of food, a torn sail, but we’re still moving south. This sweet boat tracks wonderfully and it felt like we were riding on rails! It’s a great day and I’ll save the sleep for tonight.

Fast forward a few hours to the evening. Some asshole wave came up, grabbed the jib, and with it tore the lifeline wire out of the toggle fitting! I was sitting in the cockpit and noticed the lifeline was slack, and when I went up front saw the broken safety line flopped over my torn sail. Ughh… There are no instant fixes for either of these.

Now I thought I was decent at reading the weather, but I think I misread the clouds this day. Because that second night (my time to catch up on sleep) was not a night to sleep.

The winds and waves picked up and we were moving. Every now and then a larger cresting wave would slam the side of the hull, shake the entire boat, and send water over the entirety of the length of Saoirse.

The portlight gaskets I replaced turned out to not be the problem of leaky portlights – the problem was the seal between the frame and the glass. Each wave sent a surprising amount of saltwater through the seal and into the cabin – on my bunk, the floor, the galley – everywhere. And you know saltwater doesn’t dry on its own, it just lingers in the form of a slick mess.

My sails were still mostly balanced and steering fine, so I retreated down below to try to catch a few winks and attempt to stay dry(er). I was slowly getting the sea legs back, but it was still tough to stay below. Sometimes a gust would hit and we’d round up slightly, and the sounds of the luffing sails reverberated through the cabin. No sleep. Then the waves would hit the hull with sledgehammers. A drop of water would hit my forehead. No sleep. Then the bright flashes of light.

Yep, went up top and we were now surrounded by lightning. I went back down below to turn on my radar and identify the storm cells. The radar that I had just tested days before was now not powering up. Nothing. Are you fucking kidding me? Okay we’ll do this the old-fashioned way. Hope and pray.

Not knowing when a giant gust of wind would hit, I untied the tiller and started steering by hand. It was “darker than a bag full of assholes” as a friend used to say.

The big gusts never really hit, and neither did the lightning. It just kept illuminating clouds miles away every so often.

Waves would break over the side and soak me with saltwater, then some tease of a rain shower would come by and promise a fresh rinse but not deliver.

The storms seemed to pass, but I couldn’t go back down below because I was soaking wet with salt. I could have changed clothes but I just really didn’t want to be down there at that moment. It was stuffy, wet, and salty. I sail in Caribbean storms like that in bathing suit bottoms and a lightweight jacket.

So instead I retreated to the soaked cockpit cushion and slept for a few minutes at a time, usually woken up by a wave breaking over me. Dawn couldn’t come fast enough.

At some point I went down below for something, I don’t know what. “One hand for the boat” wasn’t enough because as I descended the steps, a wave hit and sent me crashing into my navigation table. I put a hand out to stop the fall, and my hand found the Brita water filter attachment on my galley faucet. The poor plastic faucet threading didn’t stand a chance and tore out without a fight. Add one more bruise to the ego and one more giant bruise to the collection I was getting on my body.

150 miles down, 175 left to go. Almost there. Tell me again why I’m doing this?

Now, for those of you asking why I didn’t just tuck into a nearby island (30-60 miles away)…those islands aren’t “nearby” when they’re all within 50 degrees of the wind. Now that would have taken forever and been far more uncomfortable.

This is about the time everything started talking to me. Like delirium. Lack of sleep. I’d only had a small collection of naps in the past 36 hours. The alarm timer was set for 30 minutes, but between starting the alarm and the end I could really only count a few minutes of actual sleep in that time.

Every wave clapping against the hull, every ring in the rigging, every collapse of sea foam was a child whispering, a dog barking, or a man answering the telephone. Really like not kidding, that’s what my brain believed. It was fun.

The sea finally went from black to slate gray, and finally to a lighter look of liquid mercury. I couldn’t see the sun but I knew it was there, and from the clouds knew I was in for some more wind and rain today.

One rather big shower did hit that morning and it was great – I scattered all of my salt-soaked clothes, hat, and other gear throughout the cockpit. I stripped down and kept one hand on the dodger frame and one hand on the tiller. Sailing into showers like this is kinda fun – you see the ripples on the water start to increase and the wall of rain coming towards you. Wait for it…wait for it…. It dumped a lot of fresh water on everything.

Before this storm hit it had flattened the sea, and now I had fifteen knots of wind with only small one-foot lumps of water to power through, and we owned it. It felt like we were planing (impossible in a 10,000-pound sailboat).

Once the shower passed I went down below to towel off and change into dry clothes. It was a relief to get all that burning, itchy salt off of all of me.

As I stared out of my companionway and into the cockpit, I noticed something on my wind vane tower just didn’t look right. An intentionally bent rod that is supposed to be held fast by a pin was just flopping around. I reinstalled the pin through this rod and the wind vane immediately started steering the boat for me. Hallelujah, two big morale boosts in a row!

It sure didn’t feel like it but this was only my second full day. Only 36 hours had passed up to this point, but to my mind and body it felt like weeks.

The rest of this second full day was mostly gray, but it was dry, the winds were fairly consistent and the seas were cooperating. I was finally at the point where I could retreat down below to read a little, watch some TV shows on the iPad, make popcorn on the stove, take a few power naps, and just live like you’re supposed to while on passage.

You know, things that actually make it enjoyable.

Just hours ago I was cursing everything, and now I was wondering if I should just skip Grenada and continue to South America. Because this is fun.

“The days pass happily with me wherever my ship sails.” – Captain Joshua Slocum

The day pleasantly passed into night, a night without a single cloud in the sky. The moon didn’t come up until early morning so I had plenty of time for stargazing. I’d turn off my navigation lights for small periods at a time and just sit there in complete darkness, a hundred miles from the nearest land, land that already doesn’t contribute much to light pollution.

With the arrival of the third day, the GPS finally ticked down from triple digits to double digits remaining to my destination (oh how I envy the older sailors who didn’t have that thing to stare at all day).

Now that I had identified all of the weak spots and repairs to be made in Grenada, I was again able to enjoy the third day and fourth night. I arrived offshore of Grenada just after midnight so I hove-to and waited out daybreak, catching up on some sleep in the form of thirty-minute naps interrupted by a five-minute alarm to watch for other boats and check my drift.

Grenada welcomed me with a sunrise like none other. I found a place to drop the anchor outside of St. George’s harbor, welcoming my first day and night on the hook (back in Saoirse) since 2013. I’m quarantined on the boat until Customs & Immigration open on Monday, but food and rest seems like a fine alternative in the meantime.

The project list has been arranged into categories from “do it yesterday” to “sometime before leaving Grenada”.

Which could be months from now. At the earliest.

Am I the only one who can make 325 miles feel like 1,000? What’s your worst experience?