Tangled at sea

A tale of sails, snorkels, and sharp objects.

Coral gardens

Did you know that the local university in Key West, Florida maintains “coral gardens” deep under the sea? When I first heard this I imagined wooden planter boxes, like my wife keeps at home, sitting on the ocean floor filled with coral starters. While I doubt they are in planter boxes, the coral is grown and tended there, then transplanted somewhere else once it is growing well.

This means the university students take regular dive trips about four miles off the coast of Key West to tend their gardens.

While I never saw the gardens, they are an important part of my story.

A shipwreck we explored a few days before this story
Our crew (except for Ashley and I)

January 25th, 2014

The weather was near perfect, making for the calmest day we’d had out on ocean so far during the trip. Half our group was exploring the old town in Key West, while the other half took our chartered 40 foot catamaran, named the Neverland, out for a day of sailing.

With a smaller, more dedicated crew, our plan was to motor outside the reef while the winds were light, try some fishing in deeper water, and then practice sailing, before heading to the marina to pick up the rest of our group for dinner.

Our 40ft catamaran

Since Philip (my brother-in-law) and I were learning how to run the boat, Ray—Philip’s uncle and our captain for the week—gave us control of the boat. Only stepping in when we gave him a job or thought we were about to make a hazardous decision.

With little effort we slipped away from dock in Key West and headed out for deeper water. I was at the wheel while Philip and Ashley (Philip’s girlfriend) stowed our dock lines and fenders. During the entire week sailing we spent a considerable amount of time monitoring the sailing charts (both printed and electronic on the GPS) to watch the depth where we were headed since the waters in the Florida Keys are famously shallow. Often depths of 20 feet in a narrow channel would turn to 3 or 4 feet if we drifted even a few yards off course. That’s a problem since our boat drafts 4.5 feet. While we never ran aground, I did accidentally navigate us into an area where we only had 2 feet under our rudder. Oops!

Once we left the harbor we made a straight line to open water. With the twin engines on the catamaran we could make travel at 6 or 7 knots (nautical miles per hour), which put us outside the reef in just under an hour.

Lobster pots

Normally this would be fairly boring and routine, but the lobster harvesters in the Keys decided to cure any boredom from sailing in straight line by placing lobster pots sporadically in our path.

Lobster pots are small boxes placed on the ocean floor to capture lobsters. They also have a long rope that runs from the box to a small round buoy on the surface. Run over one of those lines with either propeller and it will quickly tangle—potentially causing serious issues.

Once outside the reef we threw fishing lines in the ocean and trawled slowly to try to catch fish for dinner. We got a few bites, but didn’t end up catching anything.

Swimming with the dolphins (sort of)

But we did see dolphins! After watching two dolphins play around our bow for a few minutes we decided, why pay hundreds of dollars for a “swim with the dolphins” tour group when we could just do that from our own boat? Time to jump in! Or rather run downstairs to our cabins, change into swimsuits, then gracefully slide into the water in order to not scare them away.

60 seconds later when I was back on deck ready to get in the water, the dolphins were gone. Oh well, at least we tried.

After returning to fishing for another half hour Ashley decided she was getting cold and changed back into her jeans and sweater. Within five minutes we spotted the dolphins again! I guess they were just waiting for her to be unable to get in the water.

Alright, I just watched the video and maybe I wasn’t as graceful as I first thought.

I ran up to the bow and slipped gracefully into the water. I quickly noticed two problems: it was hard to swim with the waves and even opening my eyes under water it was hard to see. Ashley tossed me a mask to wear and Philip jumped in as well.

I never saw the dolphins again, but Ashley said that she watched the dolphin shoot away from the boat as Philip hit the water with a splash. As we were deciding whether or not to stay in the water (in hopes the dolphins may return), Ray yelled, “I’ve got a fish” from the back of the boat.

Philip and I swam to the steps on the back of the boat and climbed aboard to watch Ray reel in his fish—except, when he got the line closer the fish was gone. We struck out that day fishing.

Captain (and uncle) Ray and Ashley


Done fishing, we then decided to practice raising and lowering the sails as well as tacking and jibbing (the winds were quite calm). After about 30 minutes of practice, while we were taking the main sail down, Philip noticed that the rudder was suddenly not turning. We were using the engines to keep the boat pointed into the wind while we took the sails down and something had gone wrong. Philip quickly shifted the engines into neutral and then shut them off entirely as we realized we would have to investigate why the rudder no longer worked. Most likely, we hit a buoy for a lobster pot and tangled the line around the rudder.

Philip grabbed a mask and snorkel and headed for the water. We thought this would be an easy fix (the rudder is three feet long quite wide—hard to tangle something tightly around it) so I told Philip I wanted to see and to wait a minute before he fixed it so I could see as well.

Once we were both in the water we dove down and took a look. The rope was looped around the rudder right where it meets the boat, but also had one loop around the propeller. We still thought it would be a quick fix. Philip swam on one side of the rudder and I was on the other as I tried to hand the rope around to him. It wouldn’t budge.

Philip and I strategizing

Even with the engines stopped we were still drifting and pulling the lobster pot along with us. the tension on that side of the line was making it really hard to work under water. We swam up, told the rest of the crew the issue, and they gave us a 3 inch folding knife clipped to a rope (in case we dropped it).

It turns out, even with a taught rope, it was hard to maneuver the knife under water. With each wave we would be pushed up against the boat, then pulled away up to two or three feet. That kind of movement underwater, while trying to breathe through a snorkel and maneuver a knife, was rather dangerous. Especially with two people right there. So we decided that one person would work the knife and the other would stay back a safe distance from the blade.



Philip got the line cut and just after that I saw a large milky object floating just beyond his shoulder. After my calm, but slightly frantic gestures he turned and saw the large jellyfish just a few feet away! We swam away from the boat and saw a few more jellyfish floating there as well.

I’ve never been stung by a jellyfish and have no desire to change that. We’d encountered a few jellyfish earlier in the trip, so I’d searched Google to see if they were all dangerous. Turns out it’s just Box Jellyfish that can kill you, and they are found near Australia and the rest of Oceania (I’m pretty sure the entire continent is out to kill you). While the jellyfish near Key West wouldn’t kill you, a sting would still really hurt.

One website I read was targeted at scuba divers and said divers didn’t really need to worry about jellyfish (that’s encouraging!), because they stay near the surface (divers go deep) and only sting bare skin (most divers where wetsuits), so they are really only a threat to swimmers and snorkelers. Yikes. The reassurance I felt after reading the first part of the website was quickly gone when I read that jellyfish would be a threat to us since we are snorkeling in just swim shorts.

Anyway, that’s what I was remembering as Philip and I tried to work while staying away from the threat of stinging pain the jellyfish represented.

Even after cutting the line to the ocean floor the rope was so tight that we couldn’t pull it free from either the propeller or rudder. As we tried to work the rope free Ray said, “Philip, you may want to get out of the water.” I was on the surface, so I heard this and looked over to see Philip rocket out of the water onto the back steps of the boat as though he had rockets strapped to his feet. I looked over, saw the flock (can you call them a flock?) of large jellyfish he was avoiding and quickly swam away. I don’t think I overreacted, but Ashley said that from the boat it looked like both Philip and I were terrified! We did move fast, but I wouldn’t read too much into the comments from the rest of the crew since they were just observing the danger from the safety of the boat.

A new plan

Once the jellyfish were gone I climbed in the boat and we talked over our situation. Our rudder had hit the rope first, then the rope had become caught in the propeller, which wound it tight as the propeller turned. We only had half a loop around the rudder and one and a half times around the propeller, but it was wedged so tightly we couldn’t move it at all. Even swimming under water, placing both feet on the rudder, and pulling as hard as possible wouldn’t make it budge the rope from the rudder.

At this point we were at least six or seven miles from shore and needed to get this fixed. With only one working engine and no ability to steer, it would be impossible to make it back to shore without serious help. But if we got the rudder free, then we could use our one working engine to make it back to shore (at a much slower speed), while using the rudders to counteract the turning force from using only one engine.

At the very least, we had to get the rudder free.

Philip snorkeling (on a different day)

Back in the water, Philip and I took another look. We were exhausted from all the work (it’s hard to hold your breath, swim under water, and then pull as hard as you can), and so we looked for another plan. Luckily one side of the rope was long enough that we could pull it up on the boat, then by walking it over to the steps on the other hull of the catamaran, we could pull at the correct angle.

We didn’t get it free, but we did feel it move a little bit. That was progress!

A little hope

I jumped in again and swam over to look. I couldn’t see an improvement, but decided to pull again—with both feet on the rudder for leverage—to see if anything changed.

Success! It pulled free. Our pulling together from on the boat had loosened had made a difference. Now we were feeling good. With the rudder free we could make it back to shore (albeit slowly) on only one engine. That also meant that we had more rope and angles to work with to get the rope free from the propeller.

After more strategizing, tugging, and a lot of holding our breath, Philip and I both took a break. We couldn’t pull the line out. Time to switch back to knives.

I tried to get the folding knife up to the rope on the rudder, but only the back half of the blade was serrated and because of the width of the handle, I couldn’t get onto the tightly wedged rope.

We then tried a cheap steak knife from the galley that could reach the rope, but was still flimsy. Since we couldn’t cut the rope the short way, we had to try and cut it lengthwise into a bunch of smaller pieces. Basically the goal was to make it so much thinner that we could pull it out. The process was to take a deep breath, swim down, cut for as long as we could hold our breath, then come up for air. And repeat.

Little particles were floating off the rope, but we couldn’t see any other visible progress. It was also really hard to stay close enough to the boat to cut on the rope when the waves were buffeting both the boat and us in the water. A few times I got slammed into the boat pretty hard and got a small cut on my shoulder.

Ray decided to run a rope around the hull with loops tied on for handholds. Philip and I could then use this to stay close to the boat while sawing away with the steak knife.

I eventually found a position where I could hold my self close to the boat, keep my snorkel above water, and still reach the rope with the knife. I’ve never been so thankful to have long arms!

Even after staying working away for a few minutes straight I still hadn’t made much progress and the wind had picked up making the waves bigger. I decided to come back on the boat to rest.

Taking a break

Sitting on the boat, talking with Ray, we decided that we didn’t know if we were going to get it free, both Philip and I needed to rest, so during that time we might as well get a little closer to shore by trying out our one good engine. I stepped inside out of the wind and had a sandwich Ashley kindly had prepared. I was surprised that we could get going at 4 knots on the one engine while still controlling our direction. Since our normal cruising speed was 6 knots, we weren’t too much slower.

The hard part would be navigating to our slip in the marina without the turning ability (by putting one engine forward and the other in reverse) that we were accustomed to. So it was still important to stop soon and work on freeing the rope again. Thankfully I never had to go back into the water.


After cruising for less than five minutes we changed course to avoid another boat. I didn’t think much of it until Ray looked through the binoculars and said “That’s a dive boat!”

The dive boat

Sure enough, after not having seen a dive boat the entire trip, we came across a group of scuba divers right when we needed them most. We called them on the radio, explained the problem, and asked for help. They said yes and they said to come closer so they would send one of their divers over. But they asked that we skirt wide around their boat since they had a group of divers (mostly college students) tending to undersea coral gardens.

As we got closer we saw a diver jump into the water, be handed a large knife by the crew on the boat, then swim towards our boat.

He swam up, asked which propeller was tangled, and then went under water and got to work. We waited and talked about how much easier it must be to work on getting the rope free when you didn’t have to worry about holding your breath.

He didn’t resurface for 20 minutes.

When he did finally come up he said that he had made progress, but that it was still stuck on there. Only then did we see that the knife he was using was a large fish filet knife that was not serrated. So we traded him for our smaller, but serrated steak knife.

He went under again for another 15 minutes.

Once he came back up, the first thing he pointed out is that as we had been drifting a rope from another lobster pot had become tangled around our other rudder. Since we were moving so slowly it didn’t have much tension, so it was easy to get free from it. But the second rope just made us more frustrated with these floating obstacles (and the people who put them there).

Once the diver said the rope was free, he climbed aboard, we fired up both engines and took him back towards his boat (which we had drifted about quarter mile from). We thanked him profusely and learned that his name was Alex.

After he returned to his boat we headed home. But not before finding out his full name and an address where we could send a check. We were very thankful for his services!

Talking it over later we realized that if it took 35 minutes for someone with a scuba tank to get the rope free, we probably never would have been able to get it ourselves with just snorkel gear.

Sharing stories over dinner inside the boat



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Nathan Barry

Nathan Barry

Founder and Designer at ConvertKit. App designer, writer, traveler.http://nathanbarry.com