A Story of Sailing, Sleeping, and Everything Breaking
I recently had the privilege of joining on a sailboat delivery from Maryland to The Virgin Islands. I’ve dreamt of sailing and the open ocean for years, so joining the crew was a dream come true. Read on to find out what it was like spending 16 DAYS AT SEA.
If you’d like to watch our adventure on YouTube, I’ve put together this clip below. For additional clips, follow me on Instagram.
Pre-Trip
After two rough days of travel, I finally made it to Annapolis, albeit with one fewer sandal (thanks a lot American Airlines). A storm had the water levels in our little neck of the Chesapeake Bay higher than theyβd been since the 1930βs. Thankfully boats float, but we waded through a foot of water walking along the dock. After some bourbon to keep us warm in the 35-degree weather, we settled in.
We were held up at the dock for over a week by unfavorable weather in the Atlantic, but I wasnβt too upset. The delay allowed Delaney to join us. This turned out crucial, because she ended up joining the crew when another member had to back out. We frequented a local yacht bar, and the other sailors at the marina were probably annoyed by our nightly swims. There might have been rum involved, but we’re sailors, right?
Meet the Crew
From left to right.
Deck Hand: Delaney – βBringer of feminine energyβ. Last minute addition.
Cabin Boy: Me! Grady βTreeβ – Doesnβt fit in the bathroom. Chesapeake Bay midnight swimming club member.
First Mate: Jay – Good at saving the day. Uses a 10-year-old iPod.
Captain: John – Likes video games. Hates cooking.
Day 1 – Time to Go
The excitement of finally getting underway was that same equally addictive feeling I get when beginning a new adventure. Itβs a nerve-racking-in-a-good way feeling, raw, wild. I mean, Iβve been wanting to sail for 5 years and it was finally coming true. How cool is that?
So, at exactly 8:34, we untied the lines and headedβ¦ to the fuel dock. After twenty minutes and hundreds of gallons of diesel, we finally got underway. We motored our way through the busy Chesapeake Bay, dodging cargo ships, barges, personal boats, and shallow draft areas. The weather was cold, the wind was fair, and the high was in the mid 40βs. It felt like zero to us.
Day 2 – The Outer Banks
We left the Chesapeake around 3 in the morning but kept close enough to the North Carolina shore that we still had cell service. Known as the Outer Banks, the coast of North Carolina is an endless expanse of beach, and itβs where Iβve lived the last two summers (which you can read about here).
It’s been challenging getting used to all the noise coming from the boat, but if waves were beating you constantly, you’d probably make noise too.
Day 3 – November 10th
Something Delaney and I have really been enjoying is the movement of the moon across the night sky. The moon tonight is already more than half-way across its nightly arc and disappears quickly, leaving us with total darkness save the sprinkling of stars above our sails. And when I say total darkness, I mean it: once the moon had set, you couldnβt differentiate between the sea and the sky.
Sailing in that pitch-black abyss is dreamlike. You feel like youβre floating on an endless plane of nothing. You only know where the horizon is because the boat is sailing that way. It was always slightly ominous. I did learn to relax and notice all that the sky gave us, including the most vibrant view of the Milky Way Iβve ever seen.
Day 3 also gave us our first fish. A sizeable enough tuna, we cleaned and fileted it, and Jay cooked it up for dinner.
Day 4 – Dolphins and Storms
We had our first dolphin sighting! They stayed with us for a few minutes, riding just off the bow, darting back and forth and circling the boat. It was incredible.
Later in the day, off the coast of South Carolina, we ran into a hell of a storm. In sailing thereβs a difference between a storm, something big and possibly course-altering, and a squall, a usually short patch of sky with dark intentions and light skies behind it. This was the former.
We ended up beating into the storm for hours, with high winds and crazy seas rocking us all night. We were getting thrown out of our seats and were nervously watching lightning in the distance.
Later we found out that the max wind speed topped out at 30 knots, which is sailor speak for fast as hell.
Day 5 – The Calm After the Storm
The calm after the storm should be a phrase because wow, what a lazy and quiet day. We didnβt do much, catching up on lost sleep from last night. Another beautiful sunset was our reward for braving the night before.
Day 6 – Headed for Florida
Weβve been moving pretty slow and havenβt done much sailing, so weβre running low on fuel. The plan is to pull into Florida tomorrow somewhere and fill up. Weβre pretty close to the coast so weβre starting to see more shipping activity and can make out some lights from shore sometimes too.
Day 7 – Snack Restock
Delaney and I hopped off at the marina where weβre refueling to find snacks. Unfortunately for us, the marina store only had chips and some other junk items, but despite the lack of options and premium price, it did end up proving worthwhile. Hot Cheetos keep Delaney sane.
Day 8 – November 15th
Almost clear of Florida and itβs still pretty cold at night (to us). It was probably in the low 60βs with a strong breeze.
Weβve turned east, making our way in-between Cuba and the Bahamas. This skinny little channel is busy with lots of ships though, so it makes our watch interesting. I even gave a cruise ship a show. But spirits are high.
Day 9 – Cruising Past Cuba
Weather and wind against us, we are sailing impossibly slow. I thought the trip to Florida took forever, but this trip past Cuba is painstaking. At one point during my shift, we were moving 0.8 knots. Which is sailor speak for slow as hell.
We can occasionally make out lighthouses and other things on Cuba which is cool, but we arenβt even halfway across it at this point and weβre only moving slower. Cuba is here to stay.
Day 10 – Things that go WHACK in the Night
We were woken up at 3 in the morning by a sliding glass door falling. It hit with a loud βWHACKβ that nearly turned Captain John into a pancake. Loud noises in the middle of the night on your floating home arenβt something to ignore.
(Click here to see what boat captain Duncan Molesworth thinks about boat crossings).
We caught an absolute unit of a barracuda today too. We tossed it right back, but now that weβre in the Caribbean we keep getting sargassum, a type of seaweed, caught on our hooks. Weβve started calling them βvegetarian fishβ.
Day 11 – Cuba Does Not End
I have nothing against Cuba, but weβve been moving so slow that weβve just been stuck next to it. Itβs deflating, to say the least.
At this point in the trip, everything is breaking. Our water-maker broke so weβve been extra water-conscious, but because misery loves company, a pipe fitting broke and dumped 60% of our potable water into the ocean too. We all decided to ration our water for toilet purposes and held off on less essential functions, like cleaning dishes. We survived for 24 hours on sodas and Bubly water, too.
Day 12 – This is a Maritime Emergency so let us in or We’re Going to Lose It
Running desperately low on water (and fuel. Again.) meant we had to make an emergency stop on the sleepy little Bahamian island of Great Inagua. We filled our fuel tanks, filled our water tanks, and got a few groceries. Which is good, considering we had no fuel, hadnβt showered in 5 days, and havenβt restocked food in 13 days. Imagine the languishing smell of 4 unshowered sailors coated in a thin layer of salt and sick of how slow theyβre moving and youβve got a sense of the aroma onboard.
Grocery shopping for a boat trip means buying 16+ days of food before you ever leave, so our fresh produce had long since been eaten. When you eat canned soup for the fifth day in a row, your zest for βyachtingβ wanes. I just want a fresh vegetable. Which the grocery store in Mathew Town didnβt have much of.
Day 13 – Haiti
Finally picking up some speed and doing some motor-sailing, we occasionally hit speeds of up to 12 knots. We can see Haiti, the weather is nice, and we caught an absolutely massive wahoo.
Oh and weβre starting to lose our minds a little.
Day 14 – The Dominican Republic
The weather is beautiful and our hopes are high as we pass the Dominican Republic. We can see the end in sight.
Day 15 – Puerto Rico
Seeing Puerto Rico is bittersweet. The northern shore of Puerto Rico sparkles like a Christmas tree, a welcome change compared to the dim shores of Cuba, Haiti, and the Dominican. We occasionally get cell signal too.
It doesnβt seem real that weβre almost done, but almost done doesnβt tie off the dock lines. The weather is cold enough that we still need light jackets at night, but itβs too hot to sleep in our bunks, so we’ve all been sleeping in various places on deck.
Day 16 – Sailing Home
Intense joy seeing land, but not just any land: home. St. Thomas.
Around ten in the morning we started blaring music, dancing, hoopinβ and hollerinβ, and a weight of anticipation had been lifted for all of us, with even Captain John joining in on the party.
We kept the music blasting all the way to Yacht Haven where we pulled in, tied off, and poured champagne. We just survived 16 days at sea and we’re ready to party.
Post-Trip Thoughts: 16 Days at Sea
Being on the boat came with plenty of down time, so I ended up finishing 7 books. I love to read, but itβs not possible having a book shelf while living out of a backpack, so I use an Amazon Kindle e-reader. Itβs one of my most cherished possessions. I use a website called BookBub, which sends me a daily email with a list of books on sale tailored to my interests. Some are as low as 99 cents.
At home, I sometimes feel guilty being lazy, napping, or watching Netflix. I feel like Iβve wasted productive time. But when youβre on a boat, with nothing to do when not on your shift, you donβt feel guilty being lazy. There is literally nothing else for you to do when you’re spending 16 days at sea. So we watched movies saved on our phones and laptops, listened to music and podcasts, and took numerous naps.
16 Days at Sea
Sailing on a boat out at sea is something Iβve been wanting to do for over 5 years. I’ve dreamt of being completely surrounded by the ocean with no land in sight. I’ve wanted to watch the sun set over the ocean, just to watch it rise over the ocean again. I’ve longed for the salt, longed for the wind, longed for the freedom of hanging onto the mast and staring out to sea. It still seems unreal that I ever got to do this trip, and it’s only made me hungry to go sailing again.
My first inspiration for sailing came from the movie “Chasing Bubbles” on YouTube. Chasing Bubbles is about a guy that buys a sailboat and sails the world, but itβs way more complex than that and an excellent watch. I definitely suggest everyone check it out. Itβll make you want to sail the world too.
Follow this link and watch my favorite movie: Chasing Bubbles.
I also highly suggest checking out the rockstar sailors of SV Delos. Seeing their videos introduced me to sailing, and I was thisssss close to meeting them, too.
They say you should never meet your heroes, but if sailing the ocean were my hero, I’d be happy with the results. 16 Days at Sea was an infinite number of days too few.
