PART 1 - GETTING READY
March 28th - 3 Months to Departure
Wow! How quickly time flies by! Over a year ago I kayaked around Florida. When I arrived back at my house in early February, we were on the cusp of the pandemic. I remember paddling down the Suwannee River when my mother called and asked, “Hey, what do you think is going to happen with this virus? You think it will get here?”
“I don’t know, I hope not,” I said, “but I think journeying in a kayak, I’m safer than anywhere else. It’s been two winters since I last caught the flu. If I don’t come across anyone, then there’s no one to catch anything from. We will see what happens...” Oh, how little did I know then how life would turn into a different kind of journey…
Home confinement, in a way, has been like paddling across the ocean. The change of pace in life was very different at first, even somewhat interesting to get used to the new unusual routine, but once the days of confinement began to merge seamlessly into one another I wondered if I was in a sort of spaceship it but without a destination, , and I wondered if I was going a little crazy. At least my spaceship is closer to a luxury cruise. I have the privilege to step outside once in a while and walk to Bill Baggs park under the shade of trees, hear the birds, and even see the odd dolphin chasing mullet around the harbor. Life isn’t so bad, for me at least…
One month, three months, six months, a year of confinement has now passed, but at last, perhaps this stationary journey may be close to its end, and maybe by summer it will be possible for me to embark on another great kayak endeavor. If the virus loosens its grip on our lives, my plan is to by June, set out from San Juan and circumnavigate Puerto Rico.
While I am sure that there will be many challenges, there is one thing that will not be an issue on this journey: Money! I have all the funds for the expedition, and I have it in spades. The circumstances of how this came about are a noteworthy side story; I got the money in an online casino.
About a week before the presidential election, I came across this website called Predictit.org. It’s a political betting platform, where you can wager on the outcome of elections and other things like political appointments, resignations and the passage of Bills. I was a bit skeptical because although political gambling is legal overseas, it’s most certainly not in the United States. However, from what I gathered, the site is indeed legitimate. Like many laws in the Code of Federal Regulations, there is a loophole. You can run a political betting house in the United States, if you do it through an accredited university, make it a research project, and add a few guard rails so compulsive gambling fools don’t lose their life savings on a single bet. Each wager works like a derivative trade. If you want to bet on the outcome of a race, you make an offer to purchase shares on the outcome (between 1 and 99 cents per share) at a certain price; if someone on the opposite side of the bet accepts the offer, then a contract is created. For example, if I offer 40 cents per share that the Democratic Candidate for president will win Michigan, the system finds someone who is willing to bet 60 cents per share that the Democratic Candidate will lose. Once the outcome is known I will have earned 1 dollar per share if I’m right or pay 40 cents if I’m wrong. Given that there are thousands of trades until the outcome is known, the market value on any contract goes up and down with the wisdom of the crowd, and I can sell the contract before expiration like an Option Call, if I see a price movement in my favor.
Some crowds, however, can be wiser than others. Dumb crowds let their opinions be swayed by their collective delusions, and the Predictit chat forums are a den of voter fraud conspiracies and rumors that make the price of certain contracts swing wildly in a few hours. And this crazy volatility is an opportunity.
I am not a good gambler, but I am a reasonably smart gambler to know that games of negative expectation are not worth playing. If you want to make money gambling, you need access to information that indicates when the expectation is in your favor. That’s why you can make money in Black Jack counting cards. If you bet more when you know the odds favor, you can come out ahead.
So, a thought came into my head; what if I compared the betting odds from Predictit with some readily available polling models like Fivethirtyeight? Could there be a wager out there where the polling model would indicate a higher probability of outcome than the betting market? Could the polling model be smarter than the collective wisdom of the crowd? I thought that was worth investigating.
I set up a spreadsheet and calculated the Expectation for each state and senate race, and compared the probability from the polling models with the cost of the bet if I lost, and payout if I won. To my surprise, there were quite a few wagers (all of them for the Democrats) with an Expectation greater than 1.2, after fees. That meant that if I spread my money on enough of these wages, the rule of large numbers would work out in my favor and I would be nearly guaranteed to make money. I picked the 20 best bets and spread $9,000 between while minimizing the correlation between different races (like making sure that I didn’t bet on the democratic candidate winning, and that the next vice president would be a woman, because those two bets are 100% correlated).
My spreadsheet projected an expected return on investment of 18%, a maximum return of 40%, and a 90% chance of at least breaking even. I thought those were good odds… so I plowed into the “investment.” A month after the election when the last betting market closed I made about $2600 profit and was on the right side of 18 of the 20 races (Yes, it was darn Florida that cost me dearly…).
I don’t like to mix politics with kayaking, but I have to thank the thousands of anonymous Republicans out there who believed enough in Donald Trump’s lies about election fraud to back their misguided conviction with their money, even after it was evident that the result would not go their way. Those fools are paying for my new Epic carbon wing paddle, a kayak shipment to San Juan, and a few hotel nights!
April 11th - 2.5 Months to Departure
I had forgotten how much work it is to plan an expedition. This journey is far more complicated than circumnavigating Florida. A year ago, all I needed to do was to dolly my kayak out of my living room onto the sand, take a few back-and-forth trips for the gear, and give a strong push off the beach. This time the kayak, and everything and everything that goes with it, has to somehow find its way across the Caribbean before I can even look at the waves in San Juan and contemplate the feeling of whether or not or not I make it back to my starting point. There will hopefully be a time to think that, but it isn’t now.
Flying the kayak is out of the question. Air shipping with FEDEX or UPS is more than $400 per bag, each way. I have three very large bags, and too much respect for money, even if I would be paying for it with tainted Trump money.
The clearly best and only option is to send the equipment by sea. I dug around Miami and I discovered a company called Crowley Maritime that sails a cargo ship to San Juan once a week. “If you can fit it on a pallet or two we can ship it.” said a lady over the phone. “You’ll need to have the three bags with your kayak at our facility for us to give you final pricing, but from the measurements you provided, it will be around $200 total. The ship sails Wednesdays and arrives on Sundays.”
“Oh, that’s expensive, but much less than air shipping. How much of that price comes from the Jones Act?” I asked jokingly.
“We don’t have a line item for it.” She responded with a sharp quip.
The Jones Act is an obscure law from the 1920s made to shield American shipbuilders from competition. It states that if you ship anything between two American ports, then it has to be done on an American made ship, with an American crew. We in the mainland usually don’t think about it because so much of what we buy moves by rail, truck or plane; imagine the inconvenience if to send something using FEDEX, you had to use a truck made in a US factory, with an American truck driver, or if you wanted to fly between Miami and New York, the plane couldn’t be an Airbus. Alas that is how it is with sea shipping. Puerto Ricans get squeezed by the Jones Act. I remember hearing that when hurricane Maria hit the island in 2017, there weren’t enough qualified ships or crew to bring in supplies from the mainland and a lot of time was lost in the relief effort.
“Oh, and remember, there is an 11.5% excise tax on the value of anything you are importing into Puerto Rico, even if you are coming from the mainland, ” said the Crawley lady.
“But I don’t remember how much my kayak cost me, and it’s used. Who knows how much it’s worth now. It will go back home with me when I’m done going around the island.” I said with concern. The kayak, plus all the gear is easily $5000, what that would mean a bill north of $500 at least. “Well then you can declare it as a personal item, which would not be subject to the excise tax, but it might have to go through inspection, and that could tie it up for a week, maybe more. We can hold your cargo for 6 days once we receive it in San Juan and it clears inspection, so plan accordingly.” That won’t leave me many days to plan ahead of time to book plane tickets.
April 18th - 2 Months to Departure
One of the things that has been grinding in my mind about the journey lately is the North section of coastline from San Juan to Rincon. I looked at it on Google Earth; the coastline is exposed to the Atlantic swells, and the waves there can get very large. If I google Puerto Rico Surf, I get shown several videos of surfers riding huge barrel swells, some so large they take a jet ski to get on the wave. It’s humbling to watch and think that I may be out there, but with no jet ski to save me. Having no kayak surfing practice is one of the things that bothers me about kayaking in Miami. Even a mile out to sea, the water depth is hardly ever more than 12 or 15 feet, and the waves are almost always very gentle. It takes a sustained wind from due East of 25 miles per hour or more to make meaningful waves, and even then, you’ll have to paddle into that wind for a while, before you can turn around to catch anything. And of course, you have to hope that the blue boom kayak surfing day falls on the weekend, and you’re not too busy. Most of my kayak surfing practice happens when I travel to kayak somewhere else, so not much practice…
I was connected through Facebook to a paddler in Puerto Rico. We chatted over the phone, and I explained to him my plan to go counter clockwise around the island. “Oh yes, the North Coast around Isabela and Rincon can be quite rough, but in the summer, maybe it’s not so rough. Pick your paddling days according to your ability, have a good roll, and don’t be pressed for time. That’s when you make mistakes and go out when you shouldn’t,” he said.
“I have about a month,” I said.
“Oh, that should cover you. You don’t see many Puerto Ricans in a hurry most of the time. When you’re out there you can give me your GPS link, and I will keep an eye out for you. Maybe I join you part of the way.” I would not mind some company on the North Coast.
I went out for a paddle after work in the afternoon. When I arrived back home and was washing the kayak, I noticed that the electric bilge pump was not starting. “Perhaps the battery needs charging”, I thought. When I opened the waterproof battery box, however, I noticed there was moisture in it, and the inner foam insulation was smeared with a light orange rust. The gaskets around the cable orifice were not quite as water tight as they seemed. I always feared this might inevitably happen someday. Do-it-yourself electrical equipment set up and sea kayaks are a risky combination. I will fix it this time with a new battery, cables, some calking, and add an extra zip lock for the battery in the box, but if it fails again, I will get rid of it.
I’ve been thinking about when exactly would conditions really be so terrible that I would need the electric pump and I cannot come up with a good enough answer. The setup is about 2 pounds of weight and takes up room in front of my feet. I’m confident with my roll on either side of the kayak. Conceivably, I may wet exit if in very large surf conditions I get thumped hard on a massive barrel wave, but if that happens, am I really going to cowboy ride back into the cockpit before the next wave catches up to me? Better to point the water-logged kayak towards shore and sort things out on the beach. A solid roll is superior insurance than an electric bilge pump, and there is no weight penalty for that. Can anyone think of a situation when an electric bilge pump is really going to be indispensable? I cannot.
June 4th - 14 Days to Departure
Oh goodness! What a whirlwind the past month has been! I was working out of Colorado for all of May and the beginning of June. The different scenery of mountains, snow and cooler temperatures was a pleasant temporary reprieve from the swamp humidity of Miami. I kept my work schedule on Eastern time, so my work hours were from 6:00am to 3:00pm, and that left time in the long afternoons for bike rides to climb up to the mountain passes and villages. The constant exercise will no doubt help. I lost 10 pounds in a month. “You have no beer belly anymore,” my mother said, “well, a food belly to be more precise, you don’t drink. That will help you on the up wind stretch in Puerto Rico. Let’s hope you don’t gain it all back, again. That yoyoing you do with your weight is not good for you. You know, after 40 the general trend is up, and so are the health problems that go with being fat…”
“Well, I’m 37 now; maybe when I’m 40, if I get good enough kayaking I’ll make expeditioning a full-time gig. I have the money to do it… Then my worry will be to weigh too little instead of weighing too much.”
“Maybe when you’re 40 you’ve got a girlfriend who will get those ideas out of your head, so my head can get some rest. And speaking of heads, you’re vaccinated now, stop cutting your own hair just to save twenty bucks. That buzz cut you’ve been doing isn’t going to earn you cool points with any ladies…”
“The buzz cut is a new pandemic habit I’ve picked up. It’s great for the Miami weather. Long hair is prickly and uncomfortable, especially around the ears. And it’s not twenty bucks, it’s twenty bucks per cut, plus tips; with some 6 cuts per year that’s over one hundred and twenty dollars. I don’t spend money on things I don’t have to. As for the ladies, I have a friend at work who is 50 and just got engaged, for the first time. His fiancé looks 30-ish; so, there’s plenty of time for me to eventually contemplate that. No girlfriend would stand for me spending my vacation time kayaking for a month or more, and to be honest, I don’t think I could share a tent with someone else for a month either. My sweaty farts are bad enough for me, never mind how much worse someone else’s sweaty farts are…”
“Ah well, you know what you do with your life…. Don’t forget to send me that GPS link so I know where you are, so I can sleep at night.”
June 7th - 12 Days to Departure
Losing the food belly was the only progression towards the Puerto Rico expedition that I got done in Colorado. Now that I am back in Miami, I am in the middle of the crunch time to get things done before departure, and it feels overwhelming.
Sunday I purchased the last remaining items for the expedition, including the tent. I would have liked a high quality Hilleberg tent that I could use on future journeys, but it seems the pandemic has wreaked their supply chain; their distributors are not fulfilling orders for the next 4 to 6 months, and I ordered mine in March. I settled for a two person MSR tent which Amazon delivered the same day and I practiced setting it up in my living room. It’s a very well ventilated tent and that should be very good for the warm weather.
It was essential to have all the expedition gear on Sunday to lay out everything and confirm what will need to go, and make sure everything fits in the kayak. Fortunately, I need fewer volumous things on a warm weather expedition. Clothing is minimal, there is no dry suit, no wetsuit, and I’ve decided on no sleeping bag. That leaves room for the one thing I need a lot more of: water. On my paddles in the Miami summer, I usually drink a little over 3 liters per day. I will plan on 4 liters per day, and carry a 3-day supply, at least in the beginning; a coworker mentioned to me that the swampy heat in Puerto Rico is not as terrible as the Miami summer because of the constant East trade wind; I hope he is right.
Monday after work was my only chance to do a sea trial with all the gear in the boat. I felt that this was a crucial thing to do before leaving. If anything won’t fit, then now is the time to find out. The kayak becomes a different boat when it's loaded with an extra 40 pounds. I laid out all my things on a picnic table and dragged the kayak to the edge of the water so that the bow was floating before loading. I remember from a previous launch during the Florida journey that the gorilla crawl technique from the sand only works with a packed boat if there is a steep enough downgrade, otherwise it is too heavy to move the boat through the sand.
I divided the gear as best I could so the weight would be about even between the bow and the stern. This is easier said than done for the Taran because the bow space is so large, and the tent poles and dolly can only fit through the oval hatch on the stern. To compensate for that I usually pack the heaviest things like water and food in the day hatch behind the seat. When everything was in I was pleasantly surprised. There was plenty of room left. If I find anything on the way I want to carry, space won’t be a problem. Maybe I should have bought the Taran 16 instead, I thought. I got in the cockpit and pushed off.
The weather was just about right for an initial sea trial. The wind was blowing at 15mph so I got a good feel for what it would be like to paddle upwind; it wasn’t easy, but it was definitely doable. I will be about half way through the journey before I have any serious headwinds and hopefully stronger.
There was enough chop to make the rolls more challenging than on flat water. I did some twenty rolls on either side with and against the waves to get comfortable with the additional weight. Although I succeeded every time it did not feel natural, the center of gravity is lower and so initiating the roll is much more difficult. I think it will be prudent to take at least one day in San Juan and practice more in bigger surf conditions before taking off.
Next I tried some edging and turning, which obviously were much less responsive. There is more mass to turn, and the mass farther away from the center of gravity. That, however, did help with holding my heading down wind on some small swells, although it takes much more effort to catch them, and when the bow caught some air, the boat sank into the wave like a knife cutting a loaf of bread.
Using the sail was not a problem. I felt that I could hold a heading closer to the wind than with an empty boat. That must be from the boat being an inch or so deeper in the water which helps resist some slippage downwind.
I squeezed as much practice as I could from the afternoon and came back to shore sometime after 9pm in the dead of night. There won’t be another training opportunity until I am in San Juan. Tomorrow the boat and gear have to get delivered to Crawley Marine for shipping. I’ll admit that I don’t quite feel ready. Not having seen what the ocean is like in Puerto Rico, I imagine the worst. Me on the jaws of huge barreling waves being tossed around like toothpicks. Hopefully four weeks is enough for me to choose to sit out the worst days.
June 8th - 11 Days to Departure
I’m glad I took the day off from work today, otherwise I would not have finished everything I had to do.
I packed the boat in the morning with all the gear in the three sections, wrapped them up with bubble wrap, and put everything inside the three custom kayak bags. This is officially the first time the bags are being used to ship the kayak, so I hope they will work as intended, because I’m the one who designed them specifically for the 3-piece Taran. The kayak and gear go ahead on the cheap through ground and sea shipping while I fly with no carry on, I pick up my expedition in a box at the destination and get on my way.
I called up an Uber XL to take everything in one go to the Crawley Marine Storage Facility in Medley about an hour’s drive away. “I have three extremely large bags, so you’ll have to lower all the seats,” I texted the driver. When the driver arrived, I felt embarrassed. She was a tiny elderly lady with scrawny little arms that looked like pencil sticks. “Sorry, but you’ll have to help me lift the big one into the trunk. It’s too big for one person,” I said.
“Sin problema.” She answered in Spanish.
We got the bag with the cockpit section on the lip of her trunk with a bit of difficulty and pushed it in. At that moment a problem became apparent. Her middle row seats were not made to go all the way down, and about two feet of bag was sticking out the back. “Well, I guess we have to go in two cars, we’ll put this one in mine and you carry the other two,” I said.
“Cabe en el Prius?” she said with raised eyebrows.
“Yes it does…”
“Ok. Que es esto?”
“It’s a kayak.”
“OK…”
She maneuvered her van so that her trunk was facing mine, and we slid the cockpit bag from one car to another without issue. For an elderly lady she sure drove fast and punched through a lot of yellow traffic lights. I had to look around for cameras and cops before I decided whether or not to follow the law. I nearly lost her on Okeechobee road when a semi-truck doing a left turn got between us. After about 30 minutes my gas light came on and I was crossing fingers hoping I would make it. I felt relieved when I saw a truck with a Crowley Marine Container turn off the road and knew we could not be far.
The Crowley warehouse is huge. I saw countless forklifts whizzing up and down aisles of boxes like it was rush-hour traffic. You had to be careful and look where you walked, the place was very noisy and hearing the incoming forklift wasn’t always possible. I filled out some paperwork at their check-in office and stepped into the warehouse; at that moment I realized just how poorly I was dressed to be there. Everyone I saw had a hard hat, reflective vests, and boots. I wore shorts, a beach shirt, and flip flops. I never wished more to have my steel toed work boots than when I saw a fork lift heading towards me carrying what looked like four refrigerators raised three feet off the ground. The driver paused next to me. “You the guy with the kayak?”
“Yes.” I responded.
“OK, go to the parking lot where you have it, and I come meet you.”
I walked out to my car, and he drove out with his forklift straddling a wooden pallet.
“How is that the kayak?”
“Yes it is. It breaks up in three pieces”
“Oh, first one I’ve seen. What you go do?”
“Paddle around Puerto Rico.”
“Oh man, you crazy! You gonna get eaten by a shark. The place is full of them.”
“That would be very bad, let’s hope it doesn’t happen…”
I helped him put the three bags on the pallet, he bundled everything together with a giant roll of cellophane wrap which at my request he used a generous amount, and then carried it off to the weighing station.
“248 pounds. Here’s your receipt, make sure you don't lose it, it has the Source Number which you need to track the shipment. It’s SMW 1511768, and my name right below it, Reinaldo Santos, if anyone asks. We’ll let you know when you can pick it up in San Juan. Probably Monday if it goes through without inspection. You pay when you pick up. It will be $256, plus tax.”
“Thank you! Please don’t drop it.”
“It won’t. The bags are wrapped with the pallet, So unless the pallet slips off the fork lift, it should be good. I’d worry more about the sharks if I were you.”
June 15th - 2 Days to Departure
I received confirmation from Crowley Marine that the Taran has landed and is ready for pickup in San Juan. I am keeping my fingers crossed that it has arrived safe and sound, and everything is as I packed. I’d hate to get there and find out that it got crushed up like a soda can in the shipping container. One of the toughest things to master in life, I think, is to not worry about things beyond my control. I can only fly tomorrow after midday, so pickup can only happen Friday morning. I’ll be worried about the kayak until I see it...
This week wrapping up work has been exhausting. Somehow work always seems to build up right before you leave for vacation; Work is one of those things that knows what you are up to, without you needing to tell it. Sort of like your bowel movement when you catch sight of the toilet. But now that the work is done, I feel a blissful feeling of there being nothing left to do here in Miami; it’s just like that moment in the can when you’ve finished your urgent business, you think, “I’m just going to sit here for ten minutes, take a deep breather, and watch some kayaking videos on YouTube. The world can afford to wait for me…”
June 16th - 1 Day to Departure
My mother always tells me that I should never have my phone next to my bed. “If you wake up at night, you’re going to want to look at it, and then you’ll see something that bothers you and then you won’t sleep for the rest of the night. I know you. Just put the thing away.”
Truer words have never been said. I woke up at 4 am to water the daisies, and of course, I took a quick look. There was a message from my tenant at 10pm, “The washer door is not opening and there is a blinking red light.” She said. Of all times, I thought, why does this have to happen the day I’m leaving.
“Try to unplug and plug it back in then re-run the washer and see if it works.” I said.
It didn’t, and I didn’t sleep the rest of the night.
I really envy those who can sleep heavy like a rock. On a good night I get 6, maybe 7 hours, because so many thoughts keep running through my head all the time; deadlines at work, politics, life projects, family, and for tonight the washer. By the time I am about to fall asleep, it’s time to wake up already. There’s not enough time for the brain machine to reboot. Even when I am asleep, it’s not a good quality sleep. I hear the AC kick on, the car that drove by in the street late at night, and the neighborhood cat squalling. I’m asleep, but I don’t feel asleep. The only time I really do sleep the whole night is when I can paddle or bike for ten hours. Only then does my body tell my mind, “I don’t care what you’re thinking, you’re turning off now.”