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June 17th - Day 1 - San Juan

The flight from Miami to San Juan took off on schedule. It was packed, but I was assigned a window seat and I passed the time looking over the Bahamas trying to make out the shapes of the different islands. I’m pretty sure we flew over Andros, the Exumas, and maybe the Turk’s and Caicos. Eventually, however, I fell asleep.


When I woke up, we had already begun the descent. I noticed the waves had many white caps like bread crumbs on a blueberry yogurt. I would have liked to know how big the waves were, to see how my kayak would compare, but I could not spot any vessel for reference. From high up above, the ocean waves look calm and tranquil.


The arrival at San Juan international airport was chaotic. Before landing I had to fill out a Covid19 status application confirming I had been vaccinated, but the online form was incredibly long filled with superfluous requirements. Why is my age needed after I gave my date of birth, or the flight information, after I gave the flight number? Strangest of all, why my employment status, profession, and employer information is relevant I have no idea. If they had just asked for my political party affiliation, that would probably be far more informative about my COVID status.


The hardest part of the application was uploading a photograph of the vaccination card. Their system would crash for lack of bandwidth, and the whole process had to be restarted. I was successful on the third attempt and received an email with a QR code, but in the end, the entire effort was for nothing. The QR code scanner at the airport was not working, and a huge line of impatient and sweaty people formed at the exit of the baggage terminal where two health officials were checking everyone’s vaccine card and temperature. If it weren’t for the masks, the collective discontent would be evident on everyone’s face. After about an hour I was finally through and on my way.

I picked a hotel close to the beach to minimize the distance I need to portage the kayak. Fortunately, I found just such a place on google earth, a hostel called the Sandy Beach Hotel on Condado beach just one building behind the sand. Adding to my good fortune, behind the hotel was a CVS and a Walgreens pharmacy with all the variety of power bars and canned fish I could ever want for the start of the journey. After my Florida Expedition, I’ve concluded that I am not the type that likes to camp and cook. The cooking stove, gas and utensils take up a lot of room, and cooking is time consuming. Although reasonable people may disagree with me, I find that smoked canned salmon, and tuna in tomato sauce are quite good.


After checking into the hotel I took a walk down to the beach. There were a few breakers on submerged rocks some distance out, and a few waves kicking up some sand when they broke on shore. I wouldn’t normally consider these to be challenging conditions, but compared to what I paddle in Miami, they would be a rough day. I looked to find the best place to  launch from. The beach had two sides separated by some rocks. The east side was flatter and the waves gentler, but there were also lots of rocks which I would be keen to avoid, especially on the first day. The west side was quite a bit steeper, with rougher waves, but they seemed to come in sets and in between it was fairly calm; the slope would make it easier to slide into the water with the loaded kayak and the portage would be shorter, and there were no rocks. I decided that would be the launching point.


The Eastern trade wind became very strong around 2:00pm. I asked the front desk at the Sandy Beach Hotel what they thought of it. “Oh, that’s pretty usual. It’s calmer in the morning, and then builds throughout the day before dying down in the evening. You’re the guy who said you would be bringing a kayak, I would recommend you don’t go too far downwind. It will be tough getting back.”


“Thanks! I’ll keep that in mind.”

June 18th - Day 2 - San Juan

Oh, what a busy day today was… At 6:00am I took a morning walk on the beach; the wind was indeed much calmer, but the waves looked about the same. I then called up a cab and headed to the Crowley Warehouse at the port to get my kayak.

“Quieres alcohol?” Said the cab driver.

“No, I don’t drink.” I responded.

“No man! Not for drinking, it’s not even eight yet. It’s to clean your hands. Health department guidelines for COVID…”


I noticed that here in Puerto Rico, people take COVID a lot more seriously than in Florida. Every business requires a mask, and you will not be allowed inside without one. In the restaurants people keep their masks on until the food arrives, and even when walking in the street most people I see are masked. “Everyone here is getting vaccinated as soon as they can schedule an appointment. We don’t get why some of you guys in the states make such a fuss about it. When life is too easy, you worry about bull-shit.”

The Crowley warehouse in San Juan looks just like the warehouse in Miami. Same layout, same forklifts driving around like it’s rush hour, Even the forklift driver who went to fetch my kayak looked like the twin brother of the driver in Miami.

“What’s that thing?” He asked.

“A kayak. I’m going to paddle around Puerto Rico.”

“Oh man… really? There are sharks out there, you know…”

When he drove the forklift back with my kayak I felt relieved. The bags and the palette looked just like when I last saw them, the plastic wrapping looked crisp and unscarred. If someone had asked me to take a bow of gratitude to Crowley Marine I would have done so; $276 to ship my kayak across the Caribbean and have it delivered with no issues felt like a bargain, even with the Jones Act. All the cab rides I’ll be taking around San Juan for the next three days will cost more than that.

The drive back from the warehouse to the hotel went smoothly. I was worried I would need two trips, but everything fit inside just one van, though the driver probably had no rear vision whatsoever, and I had my knees pressed against my chest.

Getting the sections kayak in through the hotel lobby was a tight squeeze. To say the corridors were four feet wide would be generous; I had to hold the sections vertically in front of me and walk sideways along the narrow aisles. The thorniest portion were two 90-degree bends before the patio where I had to turn in place like a rumba to pass through. The seat section was the toughest; I had to hold it vertically as well, but one handed. It was a miracle I did not scrape the boat against the walls. I’ll need to make this back and forth journey at least three more times.

After getting the kayak to its temporary home, the next task to solve was what to do with the bags. They are huge, and the hotel front desk told me they cannot hold it while I’m gone. I decided to call my paddler friend here in Puerto Rico and he offered to hold on to them, however, he lives in a town about an hour and a half drive away, and the cab fare estimate to get there was just under $200, one way. It’s somewhat ironic that the last 25 miles were costing only a little more than the 2,500 miles the kayak traveled all the way from Florida. The last mile is always the most expensive mile. I decided to look for another option. As fate would have it, I found a storage place just two miles from the hotel. They had one 5x10ft space available for $280 for a month, more than good enough, I thought. “We only have two units of that size left, if you want it, then come by today.” I took a cab there straight away, lest I get there only to find out that my fortunes had changed.  

By the time the afternoon came around, I hoped to get some rolling practice with the kayak in the waves. However, just like I was warned, the East wind had picked up considerably late in the day. I looked at the beach and decided to wait until morning. That’s a lesson to remember while I’m here; start early, finish early.

I decided instead to take a walk and scout this section of coast line to see what kind of conditions to expect. The waves got bigger the farther west I went, the beach narrowed, and the sand strip gave way to a stretch of cliffs before ending at a small bay straddled by a bridge. A few waves were breaking offshore in some underwater mount that was popular with surfers who were catching some barrels at that spot, but I made a mental note to keep an eye for the foam pile and steer far away from it. Underwater rocks are the thing I fear the most. One bad bang, and I’ll be patching the fiberglass hull.

June 19th - Day 3 - Dress Rehearsal Day

I got up at 5am to put the boat on the water with all the gear and get some rolling practice. The wind was much calmer which gave me a good feeling. I set up the kayak sections on the street and wheeled the boat up to the sand with my dolly. The beach was empty, except for two local hobos asleep on top two stacks of hotel beach chairs. I set the kayak down on the sloped side of the beach and made three trips back to the hotel to grab all my gear. I packed everything into the hatches, put on my helmet, sat in the boat, and waited for a gap in the waves. When the gap appeared, I gave two strong pushes and the boat slid down the fine wet sand with ease and I started paddling fast past the breaker zone.


The water was choppy, but paddling didn’t feel strenuous. I practiced a few rolls with both my euro blade, and the wing paddle. To my great relief, the rolls felt natural, and I wasn’t getting the issue where the added weight makes starting the roll difficult. I rolled both on my good side and my offside, and both with the swell, and against the swell. That gave me a strong boost of confidence that if something bad happens, I won’t need to do a wet exit and reentry, probably.


I then practiced a few launches and landings through the surf. For the landings I got right up to the breakers just 15 feet from the sand, there I did four strong backstrokes to let the wave behind me pass underneath and break just up ahead for a soft landing. When the bow touched the sand I threw the paddle up the beach, got out quickly, and pulled the kayak up before the next wave. I stuck the landing every time and unashamedly would give myself an A grade on all my landings. Admittedly, however, the waves were barely over 4 feet. I’ve seen a video on YouTube where a 10-foot barrel breaks right on the sand; in those conditions, if you get the timing right, the landing would not be much different, but get it wrong, and the wave will smack your face on the sand and crush the boat on top of you.


My only complaint from today’s practice is that the Lifeproof box for the new iPhone is really hard to use with wet gloves. Something must have changed with the screen material, because it wasn’t like that on the Florida journey. That will make it hard to take pictures and check the GPS out on the water.

By around 10 am the wind started to pick up and I felt I’d had enough practice and built up enough confidence. No need to push things too hard on the first day.


I spent the rest of the day sightseeing in San Juan. The city feels a lot like Miami. Everyone speaks Spanish, all the cab drivers play salsa on the radio, and there is near continuous rush hour traffic. I noticed one peculiar thing on the city map, almost all the place and street names are Spanish, but there’s a few American oddities that catch the eye like Ashcroft Avenue, Roosevelt Road, Calle Lincoln, and Garfield Cut. Subtle reminders of where the latest Puerto Rico patrons come from.


From my hotel on Condado beach, I walked about 40-minutes to the old city. This part of San Juan is a contrast to the ugly modern box buildings everywhere else. Here I walked through a labyrinth of narrow stone cobbled streets under the shade of colorful two-story buildings with balconies decorated with hanging flower baskets and vines. Occasionally the street I was in would outflow into a plaza with a small fountain, a view of San Juan bay, or a tree lined square. It’s a wonderful place to lose yourself in and pretend for a moment to be transported back in time. Or it would be, if it were not for that; nearly every street in the old city is jam packed with cars bumper to bumper and there is hardly enough room for a pedestrian. All this traffic takes a toll on the place; the engine noise is constant, and many cobblestones are sagging from a load they were never designed to handle. The municipality really needs to ban all cars except for service vehicles, otherwise


Defending the old city and the entrance to San Juan bay like a closed fist is a colossal stone fort called El Morro. The walls of the fort along the Atlantic Ocean are as thick as I am tall, and it would have taken a lot of cannon balls to knock a hole through them. Unfortunately for El Morro, modern warfare has made walls obsolete. Although the Spaniards repelled the English, the French, and the Dutch, through the ages, they were no match for the Americans with their battleships and Artillery. During the Spanish American War, the US Navy bombarded El morro and pulverized a good chunk of the sea wall including the old lighthouse. The Spaniards surrendered soon after. The lighthouse and the main watch tower were rebuilt, but it’s very obvious they have a modern look to them. Inside the fort is a labyrinth of corridors, narrow passages, and some very steep inclines which I cannot imagine how many slaves would have been to drag a brass cannon up to the turrets.

After some walking around old San Juan I came across a restaurant that said it served authentic Puerto Rican food. Not knowing what Puerto Rican food is, I went with the waiter’s suggestion to try something called Mofongo, which he said was like mashed potatoes, only a little thicker as made from plantains and yucca. “Puerto Ricans love it from the time they are children,” he said. I ordered the churrasco variety, but what came was my least favorite thing to eat; green peppers and goopy onions, all of which I had to diligently scrape off. Unfortunately, the meat picked up so much of the pungent pepper taste that it was not edible, and the poor mofongo which was underneath it all was so soaked in the sauces that it had the consistency of wet bread for catching fish. I don’t think I will be ordering Mofongo again.