Tacks and Trails — A recount of a solo sail to the highest mountains of Cuba and Mexico

Tomás K Ryan

41 min readSep 24, 2017

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VIDEO of the trip — Click HERE

Rising Sails

I hear the loud noise of a desperate fly looking for freedom. I stay still staring at the ceiling while my mind drifts away thinking about what is to come. I get up, open the window, and let the fly buzz away into the morning light. Today, I will be sailing alone to Cuba.

“N/A” is the name of my sailboat which I bought a few years ago. She has been mostly sailing a patch of grass while parked on my brother’s property in Florida. Perched high on her trailer with her mast down, she looks totally out of her element. With my day job as an engineer, she has not been given the opportunity to reach her full potential. She is a Corsair F-27 trimaran sailboat adorned with three hulls built for speed rather than casual cruising. Trimarans have planing-type hulls as opposed to a displacement monohull found on common sailboats. A trimaran can surf on top of the water like a surfboard, hence the greater speed.

I feel pretty confident at the helm of N/A. We have been sailing all over the west coast of Florida. The project now is to sail south to Key West, then to Cuba, followed by another crossing to Isla Mujeres, Mexico. While there, I also plan to climb the highest mountain of each country.

Because I live and work in Boulder Colorado, I never feel I spend enough time on N/A even if I am able to take some breaks between projects. For this trip, I have planned for many weeks away from work.

N/A is now anchored in the Sarasota Bay and fully stocked for the long sail. Just getting ready for this voyage was a lot of work. The sailing machine needs to be in top condition and loaded with water, food, gear, and packed with my mountaineering equipment, climbing boots, crampons, ice axe, and all. I brought everything to N/A yesterday and slept in my shipping container home where I spent most of the night worrying about what I was missing and over analyzing what could go wrong.

I did not have to leave early since I was planning to sail nonstop for two days and two nights to Key West. Looking at the forecast on windy.com, I knew I had a few days of good sailing weather ahead of me, so there was no pressure for a specific departure time. My big brother drove me to Marina Jack, and from there I paddled my kayak to N/A who was patiently waiting at anchor. Once onboard, I prepared the sails, gear and setup the electronic charts for the departure. While inside the boat organizing all my stuff, I heard an unusual sound as something hit the hull. Listening to your vessel becomes second nature and when something goes wrong, unfamiliar noises raise alarm. I knew something was abnormal. I quickly got on deck, looked around and saw my big front screecher sail detached from the bowsprit. The sail tack was wobbling along the hull due to a busted shackle. What an improbable situation — I am not even sailing yet, the boat is still on anchor, with barely any wind or waves, so how could this happen now? N/A had been in the water for over a week and this equipment failure occurs minutes before departure rather than on a windy night when I was away. This incident would have certainly caused serious damage to the deck and hull. I felt fortunate this happened now and not a few minutes later when moving under sail. The temporary fix was a short piece of rope replacing the shackle. I took note to buy a stronger one in Key West, but for now, this was a good enough backup solution while far from a permanent fix.

A few minutes later, N/A was under sail with a soft wind carrying us south. Once on course and cruising, I started to relax and got into the groove. The sun descended into the sea, the moon rose and the wind calmed down. We are now moving at a slow four knots which normally makes me feel quite impatient. Although I prefer seven knots of cruising speed, I gladly accept these few knots N/A offers. In fact, night sailing at this speed is ideal since it allows me to relax and make a number of trips down into the cabin for short naps. It was a peaceful starry night under a full moon.

My first sunset while sailing south

As the morning came, the wind completely died and I resolved myself to start the small outboard engine. We still had many hours to reach Marco Island, being the halfway point to Key West and where I needed to fill up the gas tanks. Later that afternoon, the wind increased and carried us at eight knots to our Key West destination. This turned into another long overnight of sailing with less than two hours of sleep, but an imminent Key West arrival kept me excited. Finally, early in the morning, N/A gracefully docked at the Key West marina. After a long nap, I scootered to the West Marine store to buy a few strong shackles. I am in no hurry to sail further south — Key West is a fun town.

Two days later, the forecast showed a 24-hour window of generous northern wind for the crossing to Cuba. A noon departure seems like the perfect time to continue south and should get me to Havana in the early morning hours.

Before departure, I made sure I had all the paperwork in order. I was certainly concerned about having problems returning to the US with N/A since Cuba had been under an embargo for decades. I therefore paid a visit to the US Customs and Border Security agency to present my case. They appeared fine with my plan and stamped official papers documenting I was sailing alone to Cuba (and planning to come back…) The recent warming of relations between the two countries made everything easier. My timing was quite perfect during the few months of improving relations, and just before the Trump administration backtracked on US policies toward Cuba.

Havana Bound

N/A is sailing south straight across the Gulf current on a starboard tack. I am quite anxious as I have never sailed such a passage. I keep reminding myself of Diana Nyad who swam across from Cuba at age 64, and that makes me feel like a complete wuss! But weather conditions can make this passage either quite easy to cross or close to impassable. I sail on, fully engaged in the open water, while the surrounding waves get much bigger.

All sails are up and N/A reaches 12 knots, a speed at which everything quickly becomes uncomfortable. Going fast is fine on calm seas, but hours of this in those waves is hard on the body and the boat. It is time to take down some sails to reduce the speed. To accomplish this, you have to point the boat into the wind to relieve pressure on the sails and face the big waves head on. So N/A’s bow is pointing to the sky at every wave and it feels like a roller coaster ride. I am now near the bow trying to take a few reefs out of the mainsail when both of my feet lift off the deck as if someone cut the cable of an elevator. I fall on my side and at the same time, the mainsail boom topping lift clip fails and detaches. The boom is now out of control and hitting the deck while the sail unrolls in the strong wind, quickly resulting in a total disaster moment. N/A is totally pissed and screaming at me for my incompetence and carelessness, which I entirely deserve. The elevator has now hit bottom with a big slap and we immediately go back up on top of the next wave. Once more the bow points to the sky. I crawl toward the stern on my elbows and knees, trying to catch that massive aluminum boom with one hand. An out of control boom is dangerous and can swing to hit you, ensuring a cruel death. After what feels like an hour of ultimate fighting combat, N/A is finally under control, with her mainsail lowered and moving toward Havana at a more comfortable seven knots. I am completely exhausted and about to puke my guts out. I lay down in the cockpit covered in sweat, try to catch my breath and think about what will come next. I am just getting started.

Once I get back on my feet, I replace the faulty mainsail boom clip which just caused me all this trouble with a beefy rock climbing locking carabiner. I consider this fix to be permanent.

Full protection while crossing the Florida Strait on my way to Cuba.

To my great relief, the wind calms down for the rest of the night as I stay awake and on the lookout. I carefully keep an eye on a few huge cargos and tankers that come close to us. Not so far away on the horizon, a bright spotlight lights up the sky coming from a very specific location. Mysterious and paranormal, it looks as though someone is trying to signal aliens out of the night sky. After a while this light beam starts searching in all directions to finally lock down on me. I have to admit, it gave me the chills. To this day, I have no idea what this bizarre light was all about.

Entering Havana is a bit tricky. The channel is narrow and guarded on each side by high waves crashing on reefs. Vigilance and precision are required. I turn on the engine to gain more control and aim full power at the middle of the channel. I imagine engine failure at this exact moment and crashing on the reefs, so I double my focus to avoid abruptly ending my intimate relationship with N/A. She would have to spend the rest of her days in a Cuban shipwreck graveyard: unforgivable! We press on together and once beyond this hostile gateway, another reality opens. The water becomes still as the engine purrs slowly forward. We pass by a few shaggy houses and a guard sleeping with his rifle. We slowly progress to the immigration dock while absorbing the sight of a third world country. N/A feels far away from home and hesitates to dock on the hard concrete wall. After a little encouragement, she carefully makes contact with Cuba.

Jumping off N/A with both feet on dock, I realize my balance is off. This always happens after spending much time at sea. It is scorching hot here and the sun is cooking everything that is laying on the deck. The immigration agent, dressed in his formal uniform, approaches and blasts me instructions forcing me out of my sailor mode. After a language processing delay, I respond appropriately. My spanish is always more fluent after a few glasses of Malbec, but not today.

One official after another comes onboard, performs an inspection, and signs papers… a lot of papers. I am not even sure what I am signing, meanwhile the stamps are coming down on those thick piles of papers. I try hard to convince myself it is not in anyone’s best interest to screw with me. All seems in order, even though I am not quite certain if I am still the owner of N/A. The officers direct us to our more permanent slip at Marina Hemingway right in front of the shower building. Perfect!

That shower was bliss. N/A got a shower too. She loves to be splashed with freshwater from the dock hose to remove the salt from her hulls and sails. We feel fresh and clean as we settle down for a much needed nap. We both pass out drooling mouth open.

Cubano Times

The hot sun wakes me up and my stomach screams for nutritive content. It is time to explore the marina surroundings. I find life in a marina quite interesting as I love walking around to examine all types of boats. Some are well maintained while others are neglected to the point where you wonder how they can still stay afloat. But they still float, almost as if they are hanging on to live another adventure and prove they can cross one more ocean. Others sole purpose is the full display of the super wealthy. Apparently, according to nearby sailors, one huge ship was worth fifty million dollars. As I walked by, a crew member was vigorously polishing diving fins, so I asked him if he could do mine afterwards. He did not think I was funny.

But the best thing about life in a marina are the people who come from all over the world, each with their own story of how they got here. This is when I met Captain Philippe Pelletier, a Canadian sailor in his seventies, with decades of experience sailing alone. He had to make a stop here before crossing back to Key West and needed to fix some autopilot problem. As he was assigned the slip right next to N/A, we quickly became friends and shared a wealth of information. We had great time talking over dinner and wine onboard his meticulously maintained sailboat.

Captain Philippe Pelletier on his sailboat SurpriseS at Marina Hemingway

After a few days spent resting at the marina, I was ready to look into the logistics of climbing Pico Turquino, the highest peak of Cuba at 6,476 ft (1974 meters). Getting up this mountain consist in a long twenty kilometer hike up steep terrain. I have climbed peaks in many countries and often the best part is the travel to and from the mountain; what you discover along the way and the people you meet. Thus, the mountain height and technical difficulty is not my main motivation to climb anymore.

I decided to travel light with just a small backpack and the strict minimum. I did not have a clear plan as I was just going to wing it. Leaving the marina, I walked until I found what resembled to be a bus stop. I asked a few questions to two dudes waiting, and once they realised I had no idea what I was doing, one of them decided to guide me. We got on the bus, then transferred to a taxi eventually ending up in downtown Havana. From there we walked to the main city bus station to find a ride south to Santiago de Cuba — a fifteen hour overnight trip. In the process, the lady at the counter tells my new friend that I should not travel like a Cuban and suggests that I instead go to the beach with other tourists and work on my tan. She does have a good point however — every time I climb a mountain, I imagine myself at the beach sipping down a piña colada, and pity myself for the poor choice I just made. She then points us to another bus terminal as I am not allowed to travel in this low cost government subsidized bus system.

Once in the appropriate bus heading south, my hunger hits again. Fortunately, the bus stops at a poorly maintained roadside cantina offering not much else but ham and cheese sandwiches. This is when I get to understand exactly what I just signed up for. There are two types of currency in Cuba; the Cuban Pesos (CUP) for the locals and the Cuban Convertible Pesos (CUC) for tourists. You can therefore be overcharged for everything. Although this same sandwich cost a few cents for a Cuban, for me the unaware and naive tourist, it was set to seven US dollars (or 7 CUC). Because of this clever system, traveling through Cuba is not cheap as you grossly overpay for almost everything. Since it is illegal for me to obtain Cuban Pesos, I am not even going to try. This scheme ensures every single dollar I spend in Cuba end up in the government’s pocket, as they are the only entity allowed to issue Convertible Pesos.

The long bus ride is painful on my back and prevents me from sleeping much, but this becomes an opportunity for a unique glimpse into authentic Cuban society. Making regular stops at different cities throughout the night, I take advantage to hop off the bus and briefly explore the surroundings. I see plenty of slogans painted on deteriorated cement walls dating back from the revolution era. Those slogans are often accompanied by the famous portrait of Che Guevara, an incontestable Cuban hero. I love walking around as the people I encounter are very nice, but there is something I can’t quite grasp about their attitude in general; they certainly have a completely different approach to life.

I decide to get off the bus in the town of Bayamo. It is 3:45 am and the roads are empty with the exception of a few lonely people wandering with no clear destination. Just outside the bus stop, there is a small counter where two ladies are serving food. I see the menu on the wall which looks as if it has not been updated for decades and I can barely read the worn out text. I go down the menu and everything I try to order they do not have. The only item available is a ham and cheese sandwich, again, so I place my order. This is the exact same sandwich I ate hundreds of miles earlier; made with the same bread, same ham and same cheese for seven dollars. Pretty much everything is produced and sold by the state. If you feel like a good Cuban sandwich, go to Miami.

I walk across the street to a taxi and the driver agrees to take me to a village close to the Pico Turquino National Park. The taxi is a very old russian car which I am unable to pronounce the make. It is a total piece of shit with a gutted interior, no seat belts, holes in the seats, and paper thin doors. I carefully place my small backpack in front of me and pretend it will protect my sorry ass from a full frontal collision. As we ride into darkness, I regularly look at my iPhone GPS to ensure we are going in the right direction. I never blindly trust strangers, so I always make sure I know exactly where I am and where I am headed. Looking down at my big iPhone makes me feel weird because this small device is probably worth much more than this car, and besides, this piece of technology is in sharp contrast with everything around me right now; it does not belong to this world.

We continue talking and the driver tells me about Cuba, the economic situation and how people here in the mountains live on about one dollar per day. This is on par with many parts of Africa which I know fairly well. He tells me most jobs are provided by the state and pay around thirty dollars per month. The unofficial unemployment rate in this area is close to forty percent. He adds that a decent pair of shoes cost fifteen dollars. I proceed to look down at my $175 super light Italian approach technical sticky shoes…

The taxi driver drops me off at an intersection and tells me to wait here for a bus to the national park. After waiting over an hour, a few Cubans tell me that sometimes the bus never comes. I immediately start looking for an alternative means of transportation. One of the guys also waiting is an employee working at the park. Once he realizes I am willing to overpay for a ride, he disappears to show up later in an informal taxi; and off we go to the park!

Pico Turquino

The park rangers tell me I cannot climb the peak alone and I have to pay over $100 for a permit. This license to climb comes with a guide and a group hike to the summit the next day. Before I know it, the whole thing turns into a multi-day group-hug-type expedition and we can only start the climb tomorrow. Disappointed, I resign myself to spend the night at the park entry in a small wood shack with expansive views of the outdoors between the planks. The next morning, I begin the registration process: I go for the permit, meet the team, the guide, and fill in all the paperwork before paying my dues. After what seems like forever, we finally start hiking and I am carrying all my belongings because I am still hopeful for a self supported solo climb. With some luck, maybe the guide will allow me summit today and descend down a different trail on the other side of the mountain.

Fidel Castro spent years hiding in this forest when he was conducting the revolution from his campo hidden deep in these mountains. What a strategic spot; the forest here is so dense that it is impossible to walk through it, so the trail becomes the only access and is easy to guard.

The dense forest surrounding Pico Turquino

Again, I try to convince the guide to let me go alone to the summit and down the other side via a different trail. He refuses even after I propose him a generous tip of two months salary. This type of offer works quite well in most free market economies. I did the same while on Mount Kenya and I got a big smile back from the guide. But not here in Cuba. The guide forcefully rejected my request and no amount of tip would seem to make a difference. I slowly follow the group feeling somewhat defeated.

Halfway up, the guide falls ill with a violent stomach ache and tells us to proceed with a local porter as he rushes into the bush to relieve himself. Not without feeling some guilt, this man’s misery greatly improves my odds to reach the summit today. We press on and a few hours later we stand on top of the Pico. I tip the porter and inform him I am going alone down the other side; he smiles back delighted in acceptance. I quickly hike away knowing I will not have enough time to make it out before darkness sets in. The trail is beautiful with views over the Caribbean Sea and the surrounding mountain range. Steep and at the perfect angle, the slope puts maximum pressure on the knee joints. It is a long hike, my legs are getting tired and it is time to turn on my headlamp. Minutes later, my headlamp unexpectedly turns itself off submerging me into complete darkness. I hit it a few times when it suddenly flickers back onto my face blinding me with relief. I continue on into this unfamiliar terrain while the headlamp keeps pissing me off. I have no map, the GPS shows no path, but at least it tells me I am going towards the sea. I gulp down what is left in my water bottle. A few hours later, I hear the waves crashing and see faint lights through the thick forest. Sensing my arrival in the small village, a dog begins to bark his head off. Suddenly a bright light shines into my face as someone starts speaking to me. I slowly raise my hands to salute while faking a big smile. The guard directs me to a building summoning me to sit at an outside table overlooking the Caribbean. The sky is full of stars and the palm trees are dancing in the warm sea breeze. Exhausted and hungry, it feels like arriving in paradise, minus the nocturnal interrogation session. After a few minutes of questioning, the guard takes me to his friend who can accommodate guests in his casa particular. I am offered chips, nuts and a brightly colored orange soda which tastes so good after this long day. I ask for the possibility of hot shower and the host comes back with a large steel bucket of lukewarm water straight from the stove. Still thirsty, I almost feel like drinking it. But I instead strip down with soap in hand, and splash myself clean just like so many people do across this planet.

Back to Havana

In the guest house, I meet a Portuguese engineer who has been living in Cuba for years while working for a large foreign construction company. He has his own car and offers to drive me to Santa Clara, which is near Havana. As we ride north we discuss all aspects of living and working in Cuba. We also talk about sailing, As it turns out, he owns a large sailboat in Portugal and lives on it when home, so we obviously get along great!

Hours into the drive it was time for gas, but rather than stopping, my new friend drives right by a few gas stations. To my surprise, he tells me there is only one type of gas station where he can buy gas because all the others are reserved for Cubans and of course, charge much less. We can only buy gas from the stations that overcharge foreigners. This is probably a way to compensate for the subsidized oil Cuba has been receiving from Venezuela, which is no longer available. The Cuban state desperately needs foreign cash.

We arrive in Santa Clara just after sunset and I cannot wait to continue to Havana. I was worried about N/A being all alone for such a long time. In a hurry, I search for a taxi to take me back to the marina. After negotiating with a few drivers, I feel everyone is trying to rip me off with exorbitant prices. This is when an unmarked car blasting music off cheap speakers stops right next to me and a dude sporting the biggest gold chain I have ever seen offers to take me for a good price. I hop in and off we go. His name is José.

José drives quite slowly, which I actually appreciate. We talk about Cuba and his disdain for communismo. He also makes me listen to Cuban music, the kind we do not hear outside Cuba. It sounds like electro-pop-melancholic type music and is pretty good as you drive into the rain. José loves his country and everything it offers, but not how it is governed. Suddenly, we arrive at a roadblock and a few police officers in uniform are waving their weapons at us. José quickly admits that he is not a real taxi driver and rents this car illegally to make extra money. He also tells me to say I am a friend of his mother and just visiting. As we stop along the roadside, the police officer inspects our faces with a big flashlight and instructs José to get out the car. They move behind, opening and then closing the trunk. José seems confident and experienced at talking his way out of any situation. He comes back in the car with a nod indicating all is good. We proceed back on the road.

José tells me Cubans are not allowed to eat beef as it is strictly reserved for tourists and leaders of the communist party. If a Cuban is caught eating beef, the penalty is jail time. I asked him if he has ever tasted it before. He responds with a big smile which says it all. ”Esta muy bueno.” We both laugh in agreement. I was quite surprised about this food restriction and learning not everyone is treated the same under the law. In an economy where there is minimal incentive to produce goods, it is easy to understand the insufficient agricultural production, but much harder to understand the policy response to such problem.

Once we reach the faded splendor of Havana, I explain to José that I am actually going to the marina because I have a boat and sailed it here alone. Totally surprised, he looks at me as if I was either lying or completely crazy while shouting away some words I cannot decipher. It is now getting late and dark, but he insists on seeing the boat. N/A being a trimaran looks more like a racing machine than a typical sailboat. He hands me his phone and asks if I can take a few pictures of him standing on deck. As he jumps on N/A, she reacts a little surprised by rolling gently. José hugs her mast while sporting the biggest smile I have ever seen. I snap away a bunch of pictures. Cubans are not allowed to own boats and are forbidden to even step on one. This policy seems quite “rational” as the US is just a short sail away…

Adios Cuba

I am waiting at Marina Hemingway for the right weather to sail to Mexico. For a few days now the wind has been blowing way too hard. Every few hours I walk over to the marina hotel for an unreliable internet connection. It is a long trek to regularly check on the weather as if the more I check at the forecast, the more likely the weather will improve. After a few days of this, I finally see signs of a decent weather opening. It is time to do groceries for some fresh produce and my priority is to buy a dozen eggs. I visit a half dozen stores which are all owned and operated by the state; none have eggs. I ask a few people where I can buy eggs and all I get in return is a mocking laugh. Someone finally points me to some back alley where a dude is selling eggs from his own chickens illegally. I ask him for twelve eggs which he refuses telling me I can only buy twenty four. I am unable to convince him to sell me only a dozen, so I buy twenty four for about a dollar, and then only take half. He looks at me totally and pleasantly surprised as if no one has ever done such a thing before. I proceed back to N/A with a full grocery bag feeling like an outlaw with a plan to escape the island.

Around noon the next day everything is ready for departure. A quick stop at immigration and off we go. N/A is set free on a strong wind gust along the north coast of Cuba to our island destination Isla Mujeres. It is blowing quite hard from behind, we are on a run! The mainsail is completely rolled down around the boom and we are being transported only by the large screecher front sail. It is comforting to know N/A has a new solid shackle holding it to the bowsprit pole. The night sets in and I see no other lights, no other boats, just nothing. It really feels like we are sailing alone to the edge of the world, and I can’t help but think that getting into trouble here would be very bad. We continue like this through the entire night while I try to stay on guard. Once again, I get little sleep.

I rarely have a good appetite at sea and I slept less than one hour since yesterday, so I am feeling pretty tired. During the night, I am always on guard in case something goes wrong, especially when the wind is blowing strongly. The wind speed feels well over 20 knots when suddenly the autopilot remote I wear on my arm starts beeping and at the same time, N/A goes off course. I push a few buttons and the autopilot reacts correctly putting us back on course. A few minutes later the same thing happens again, and again, to the point where the autopilot becomes unusable. I normally feel like a pretty good troubleshooter from years of experience debugging spacecraft problems, so I set out to investigate the root cause of this anomaly. I start the outboard engine to charge the batteries because I suspect they may be empty, but it does not help the autopilot problem. I also check the voltage at different connections but cannot identify the culprit. I finally give up and go fully manual by taking over the helm. I have about six hours to go before reaching the western tip of Cuba where there is a pier suitable to make repairs. The wind increases as we enter the wide bay of Los Morros. This quickly turns into a battle because we are going too fast upwind. N/A is under stress, riding on a port tack, and I am exhausted. Overloaded, I realize how critical the autopilot really is when sailing alone. Fortunately, we now have less than one hour to go before reaching the Los Morros pier where I can attempt to repair the autopilot. I start thinking it is too windy to dock and I might have to set anchor instead. I am not sure what to do. As I approach, the wind calms down and two guys wave at me from the pier, obviously offering help for the docking. I change course and aim for the pier. After my second attempt to dock, I am close enough to throw the lines at the guys and they successfully pull N/A to the massive concrete dock. I am so grateful they came out to help me. After securing everything, I go lay down feeling I got my ass kicked.

N/A is exhausted and feeling lonely at the edge of the world, on the far western tip of Cuba — Los Morros pier.

After some rest, I start to look into the autopilot problem again, and I quickly realize the boat marine batteries are completely empty. Of course idiot me! I sailed all night on the batteries with the autopilot working really hard due to big waves and the problem started in the morning before the sun could fully hit the solar panels. When I started the engine earlier in the morning, I did not rev it high enough to supply both the starving batteries and the high demands of the autopilot. I plugged the battery charger to dock power — problem solved! This simple fix was quite a relief because I realised that having a US based company ship something to Cuba is close to impossible. The embargo still has huge repercussions regarding traded goods. In summary: do not even think about shipping stuff here.

I waited two days before the wind and waves agreed to carry me to Mexico. I left Los Morros just before noon and headed straight west to Isla Mujeres. The first few miles at sea were over shallow turquoise waters making me wonder why anyone would want to leave such a beautiful place. A few hours later, the Cuban coast disappeared and the waves and wind increased. I was a bit overwhelmed being this far and feeling all alone offshore over deep dark water. My only company was the occasional huge cargo ship crossing by as we continued into the windy night.

During night watch, I kept replaying my time in Cuba which I enjoyed immensely. In a way, I also feel the situation there is quite sad. I can certainly understand what Castro did early in the revolution. At that time, what was going on in Cuba was wrong and things needed to change. I also acknowledge the attraction of communism, but when the negative signs of such a model became apparent, the regime should have made big adjustments. Instead, they seemed to have doubled down on repression. Despite the negatives, I highly recommend visiting Cuba to everyone as it was very educational.

With the recent openings and reforms, many think Cuba will change quickly. I am a bit more skeptical. The consequences of generations living under such a strict regime must be profound. Engaging with Cubans can only encourage positive changes, however slow they may be. The communist party leaders may find it very difficult to share their delicious beef.

Hola Mexico

The Gulf crossing to Mexico felt like a long hard night as I stayed wide awake through the entire distance. The strong wind and big waves kept me busy. I had to make multiple sail adjustments due to the inconsistent wind strength and direction. Making sail changes in the middle of the night can be tiring, especially if you have to take reefs out of the mainsail only to discover it was a mistake a few minutes later, then having to go out on deck again to raise the mainsail back up.

Late into the night, we encountered a few huge cruise ships loaded with high powered lights making them look like giant christmas trees in the vast open darkness. Seeing these ships was evidence of our approach to Mexico’s abundant vacation resorts.

The wind and waves calmed down as we inched towards Isla Mujeres. I went around the island to the protected side and anchored in the bay as the sun came up. The water looked exactly like it always does on the cover of sailing magazines. I was so happy to have arrived safely and in one piece after this passage which now felt like a significant accomplishment.

I slept well into the afternoon then paddled my kayak to Marina Paraiso. My wife acting as my ground support searched online and told me via my inReach satellite texting device that Chepo was the guy to contact to clear immigration. Chepo is definitely the man! Marina Paraiso was so welcoming and beautiful; a mini resort with pool, tiki hut, exotic birds, iguanas, and plenty of cool sailors. I decided to dock here for my entire stay in Mexico. After my visit to Cuba, it felt like I was back in modern civilization with a reliable internet connection. N/A deserved this nice little resort life after so much hard work. She was again delighted to be splashed all over with crystal clean freshwater.

Mexico arrival — morning anchorage at Isla Mujeres

Pico Orizaba

I dig deep into N/A to retrieve my climbing gear, ice axe and boots. I always try to pack as light as possible but for some inexplicable reason, climbing gear always feels way too heavy and bulky. I finally manage to stuff everything into my big expedition pack. Pico Orizaba is a 18,491 feet (5636 meters) dormant volcano and to reach that height, I need a plan for a few days of acclimatization, especially after spending weeks at sea level.

To get to Pico Orizaba is either an 18-hour bus ride or a cheap one hour flight from Cancun to Veracruz. I opted to fly to Veracruz, a busy industrial city. I spent a night there near the main bus station and felt quite safe despite stories of violence between members of drug cartels. A morning bus ride took me to the small village of Tlachichuca at the base of Orizaba. Once there, I went to the Servimont climber hangout where I met Doctor Reyes, the owner. A long time ago, this beautiful lodge was a soap factory which makes it a quite unique venue. The ancient industrial equipment is still in place standing between the beds and couches. When I told Doctor Reyes that I came to Mexico on my sailboat, he got all excited and told me his uncle won the first sailboat race around the world in 1974. I was skeptical but after a quick check online, I was convinced. That race is now called the Volvo Ocean Race. That’s right, a Mexican team led by his uncle Ramón Carlin beat everyone, the British, the French, and the Spaniards; all of them! Since Dr. Reyes and I had both climbing and sailing in common, we had plenty to discuss.

I wanted to climb the peak alone and could use some help getting prepared. Doctor Reyes assisted me to get everything ready and gave me numerous valuable tips. He also provided all the food and supplies for the climb. After one night at Servimont, I got a jeep ride to the Piedra Grande Hut at 13,972 feet (4258 meters). Once there, I met people from all over the world making it a unique social experience. At the hut, I met Carleen and Jannea, two super cool women from Canada. While I enjoy traveling solo, it is always fun to mingle with good people along the way. They invited me to join them and their guide for an acclimatization hike, which I gladly accepted. During the hike, they told me they both work for LUSH, a Canadian company making high quality handmade soap. Jokingly, I told them I buy my soap from the dollar store. Laughing in disapproval, they proposed to mail me a sample box of fancy soap. HaHa!

My plan was to spend two nights at the hut to acclimatize before making an attempt for the summit. The first night was pretty rough as I felt pressure in my chest and had a big headache. I was worried to have bigger problems during altitude acclimatization as happened to me years ago on mount Aconcagua in Argentina. That trip ended with a helicopter ride down… Since then, I got a bit smarter and avoid drinking bottles of Malbec the night before a long climb, even if that greatly improves my Spanish. The next day consequences are not always worth it.

Around 2am, I briefly woke up and everything felt fine, meaning my body was finally adjusting well to the altitude. At this point, I knew I had a good chance to reach the summit the following day. Later in the morning, my two Canadian friends invited me for another acclimatization hike, which I declined because I felt the need to rest a little longer before going higher. After a few hours of more laziness, I started my second acclimatization hike up to 15,300 feet (4663 meters). I felt pretty good despite going very slowly to ensure I was not wasting valuable energy. I could definitely feel the heaviness of the altitude in all parts of my body.

I woke up at 1am and forced down a small breakfast because I am never hungry before a climb. Instead, I prefer to eat snacks periodically during the day. I headed out in the cold night under a sky full of bright stars. With the lack of air and low humidity, the sky is always incredible at high altitude. I was moving fast and felt great. I quickly arrived at 15,500 ft (4774 meters) to a place known as the Labyrinth. This a series of broken ridges and immense impassable walls that would certainly be the envy of President Trump. Apparently, an easy passage exists through the Labyrinth, but is hard to find especially at night. When I was at the hut below, I heard many stories of climbers getting lost here thus screwing up their summit attempt. I knew it was much better to take my time to find the right route than risking going off course. After trying different paths in this maze, I got nowhere, so I decided to just sit and wait about forty-five minutes for a guided party to catch up to me. I took advantage of this pause to eat and drink. Once they arrived, I followed them for about ten minutes through the Labyrinth until we reached an obvious marked trail. In no time, I made it to the base of the glacier, put on my crampons, and stepped on the hard ice. It was still dark and a long slog up a steep snowy slope awaited my heavy boots. The climb seemed interminable. Step after step, the glacier revealed another long stretch of icy snow to an invisible summit. I kept pushing, alone and without a rope. I stepped over a few crevasses but none seemed big enough to swallow me. Finally, I walked over some loose dirt indicating the volcano rim was near. Once I stepped on the summit, I received a warm welcome from the morning sun. The entire climb was done in darkness until the last few minutes just before reaching the summit.

Early morning shadow of Pico Orizaba from the summit

My toes were really cold so I took off my boots and vigorously rubbed them in the sunshine. The view was out of this world and I could see the shadow of the entire volcano printed on the plains far below. Elated, I told myself I had seen Mexico from the sea and from its highest summit. Minutes later, my two Canadian friends appeared from the mountain shadow smiling. I thought they were still far below but they were just a few minutes behind me. Happily, we snapped a few celebration pictures together.

Still on the summit, I started to feel slightly dizzy. I knew the altitude was getting to me as I did not spend much time acclimatizing. So I headed down, being very careful with those metal crampons which often feel purposely made to trip you. With the exception of a quick puke in the boulder field below the Labyrinth, I was on autopilot mode all the way down. I blame mild altitude sickness for this brief malaise. Once at the hut, I took a short nap followed by a ride down to Servimont for the night. Dr. Reyes was welcoming as usual and insisted I write my travel story in his guest book, which I gladly did.

Sunrise on Pico Orizaba summit — the entire volcano crater rim

The next morning I took the bus to the city of Puebla, then a flight to Cancun, and finally a ferry back to Isla Mujeres. N/A was once again relieved to see me back in one piece — she was ready for more adventure.

Isla Times

I often think about the similarities between sailing and mountaineering. The first which comes to mind is the aspect of engagement. Once you are high on a mountain, you are committed. Same goes for sailing offshore as you cannot just decide to give up and quit. To unravel whatever predicament you find yourself in, requires will, time and effort, as there is never an easy way out. The preparation is also similar because you need to foresee several days of gear, supplies, and plan your route considering your skills, physical abilities and condition. What makes sailing very different is the machinery that propels you forward which demand a lot of care, maintenance, and technical expertise. Performing these two activities alone requires the same mindset of self-reliance and confidence, while taking extra safety precautions because you are effectively a single point of failure.

I now needed to rest and took this time to reflect on my recent journey. I felt I had discovered Mexico. The people here are very welcoming and proactively helpful. The travel logistics were effortless, and everything was super cheap thanks to a strong dollar. Their economy is bustling and vibrant with an abundance of small businesses everywhere. Wherever I looked, people were busy working and children were playing freely in the streets after school. The food was delicious and the spicy salsa was always served on the side — to me, that is very civilized.

The next few days were spent preparing and roaming around on a scooter to gather supplies. This was also a fun way to explore the island. I don’t remember how many times I lapped that small island pretending it was a Formula 1 scooter circuit. I even once reached 36 knots! This is much faster than N/A with her top speed of almost 20 knots. But she is propelled by the wind; and that makes her super cool.

Island life presents many opportunities to talk to other sailors, visit their boats, and have someone who can sympathise with you over weather forecast obsessions. When sailors learn I came here alone and plan to sail back alone, they look at me with skepticism followed by a facial expression that says it all — “You must be freaking crazy!” Fortunately, I do not see it this way. I spend much time preparing and thinking about every eventuality while being fueled by the perpetual replay of my biggest fear — to fall off the boat when offshore. For this reason, I am always tethered to N/A. I am clipped-in as I would be on a big wall rock climb. If I fall off N/A, the consequences would be exactly the same as falling down a thousand feet vertical cliff. In fact, it would be far worse at sea, with plenty of time to see my sailboat continue on autopilot and wait for a great white shark to bite off my deplorable ass.

When I look at some sailor’s boats, I can’t help but wonder how come they have not yet perished — the boat is in bad condition, poorly maintained and they have minimal knowledge of the weather forecast. Besides, their boats can sink. Most typical monohull sailboats can sink if water floods the living quarters, and that is always a possibility. On the contrary, N/A has three hulls, each with watertight compartments. To sink her, there would need to be exactly nine holes strategically placed in her hulls. But that would not even do it because her main hull is constructed of foam core material sandwiched between two layers of fiberglass. You could chop her into small pieces and they would still float. N/A is a magnificently engineered sailing machine and officially rated as unsinkable.

Another critical aspect of safety is communication. I always sail with my inReach satellite tracking and texting device. This automatically sends my position, speed and direction every 10 minutes to a public website. The inReach can effectively replace a sailboat logbook because it can be used to keep a digital record of every observation and anomaly, all safely stored outside the boat and in the cloud. With this device, I can keep contact with loved ones and they can help me with wind and wave forecast. We can exchange about various technical boating issues, or they can simply keep me company during those long days and nights under sail. If something goes really wrong, I can push an SOS button to request help. Not many sailors have this device onboard, but I consider it to be an essential element of N/A’s arsenal. The inReach is on me at all times.

While sailing, I constantly try to be proactive. Every unfamiliar noise is investigated and I regularly perform visual inspections of each stress point. As Captain Pelletier pointed to me, one critical element is the rudder. If you lose it, you are in huge trouble. Fortunately, N/A’s rudder mechanism is entirely external and I can assess its condition many times each day.

Sailing and climbing mountains alone exposes you to difficult situations, where you are left to rely solely on your skills and test your resilience — it’s all on you. When you get into a difficult situation and faced with few options, you have to persevere even if it feels useless and impossible. This capacity of self-reliance is in some ways ultimate freedom.

On the mountain, there are a lot of random objective dangers such as falling rocks that can knock you out. Even if you are super careful you regularly expose yourself while crossing a couloir with loose rocks, or stepping over a hidden crevasse. You are essentially playing Russian roulette — if you only have half a percent chance of dying here, would you take the chance? On the other hand, climbing alone is faster, which reduces your time exposed to risk. Sailing alone seems to me much safer than climbing in general, because a bad situation usually takes more time to develop and therefore provides more opportunities to counter the problems you face.

One essential task prior to sailing back to Florida is to check on the weather forecast multiple times daily. This quickly becomes an obsession every ten minutes, and this excessive forecast analysis got me nowhere. As far as I could tell, only eastern winds and huge waves prevailed. Heading east with a facing wind would be really hard if not impossible. Ideally, I needed a southern wind, which I was told happens sometimes. However, wind coming from the southeast could take N/A back home as she was at her best sailing on a close reach. Unexpectedly, the weather improved giving us a very narrow window to make the long crossing. I was working with Captain Pelletier via satellite texting to help me interpret everything and he agreed this was an acceptable time to cross. Before leaving Mexico, you have to clear the Cancun port. All was ready and I went with Chepo to the port officer to request a departure permit for the afternoon. They rejected my request and denied me to leave. Mexico’s regulations forbid any boat under 30 feet long from leaving port when they judge the wind is too strong. Since N/A is only 27 feet long, I was stuck here with no hope as the weather was getting worse on all forecasts. I had few options; either wait here for weeks or go back home to Boulder and come back in a month. I decided to fly home and leave N/A at Marina Paraiso under Chepo’s watch.

Chepo — this great man will help you navigate the bureaucracy while keeping your boat safe

Homebound

After three weeks of waiting in Boulder, I could see the weather system was in transition and the wind was about to shift to the south. This was the best opportunity to cross the Gulf in well over a month. According to the forecast, the wind direction would change from straight east to southeast and the wave height would remain below three feet. On the spur of the moment, I booked a flight to Cancun and off I went. My journey from Boulder to Cancun was sparse with a few moments of self doubt, but an email exchange with Capitan Pelletier reassured me — it truly made me realize that nothing can substitute decades of sailing experience. Once in Isla Mujeres, I prepared everything once again: groceries, water, boat rigging. The Mexican coast guard finally granted me an exit permit as several days of soft winds were in the stars. I needed a minimum of four days of good weather before reaching Florida. This would be my longest non-stop sail and the prospect of navigating all that distance alone was a bit nerve wracking.

Everything became easy once N/A filled her sails with a generous puff of wind. A few strong gusts during the night made it exciting and carried N/A to well over ten knots. We skimmed the western coast of Cuba and then changed our course toward Dry Tortugas, the most western islands of the Florida Keys. I wanted to head directly to Key West but the wind would not let me. A few hours later, much to my delight, the wind shifted slightly more making it now possible to point N/A’s bow straight for the Keys.

During the second night, the wind increased way more than what was in the forecast. Sometimes, I guess mother nature produces unexpected regional climate anomalies. We were sailing very close to the wind, which is when N/A goes fastest, now at a consistent ten knots — I briefly saw 13.1 knots on the GPS. The apparent wind felt well over twenty knots and the waves were disorganized coming from all directions. This indicates the transition area into the Gulf current of the Florida Strait between Cuba and the Keys. I kept all sails up and reveled in the speed. I knew the rigging was working hard as we bounced from side to side through this chaotic sea. This speed was well worth it as I rejoiced in watching all those miles pile up in the piggy bank.

Once N/A is on course and all trimmed for speed, it feels like she has her own will and is committed for the long haul. By that point, I have nothing to do but watch her cut with force through endless walls of waves — she is going for it!

Over the course of this crossing, I really got into my element. Sailing alone, I felt independent and self-sufficient while moving my insignificant existence forward. I had the impression to fully master my own small spacecraft while navigating the transitional continuum between two galactic systems. What a great feeling to think we could continue like this forever.

While speeding under the night stars, a loud noise demanded my attention and N/A went completely off track facing the wind with her sails flapping. Confused, I frantically looked around half asleep. I turned on my headlamp to inspect the helm and realized the autopilot had disconnected. In fact, I could not locate the metal pin to which the autopilot arm is normally attached. I looked closely and saw the pin was broken in half. It had to be replaced. Fortunately, I predicted this could happen because I knew this pin was under constant strain. Fatigue stress got the best of it. I had a simple bolt ready that I could use instead of the pin. It took a few minutes to get a wrench, climb onto the stern, and install the replacement bolt. The autopilot was back on and N/A was once again on course with her sails whistling in the wind. Relieved, I was proud to have been well prepared to predict and fix this system failure.

As the sun appeared on the horizon, a lonely dolphin approached looking for company. N/A gladly accepted this new friend by her side and dolphin reciprocated by saluting us with high leaps into the air. Together, we danced from wave to wave to celebrate the arrival of another awesome day.

Approaching Key West, I could see a large US Coast Guard cutter vessel securing the entry. Jokingly, I told myself they might intercept. In no time, a zodiac with five men aboard in full garb and combat-ready was heading directly for us at top speed. They undoubtedly meant business. Once close to us, they yelled the expected questions: where from? citizenship? what do you have onboard? any other people with you? They finally decided not to board N/A for inspection by justifying their unfamiliarity with a trimaran under sail. Giving two thumbs up and smiling, they instruct me to contact the Coast Guard cutter by VHF radio to complete the remaining formalities.

“US Coast Guard, US Coast Guard, US Coast Guard, this is sailing trimaran November Alpha approaching from the southwest with a Key West destination — over.” A few minutes later, we were cleared to proceed.

Arriving in Key West felt like coming home. I decided to continue straight north without stopping. The weather was calm and we were cruising at eight knots on flat water. Once on the north side of the Keys, it felt like sailing in my backyard. It was pure sailing joy all night long.

The next day near Fort Myers, the wind died and it looked like it would not come back for a long while. By then, I had phone coverage and called my big bro for a pickup at the Punta Rassa boat ramp. He agreed to come with N/A’s trailer.

It was time for N/A to fold her two large wings and lower her mast. It took us multiple attempts to get her to embark on the trailer as if we were forcing a wild bird into a cage. We finally got her out of the water and drove back to Sarasota during the night. I arrived in my shipping container house in the early morning hours. Exhausted, I passed out in peace — the voyage was over.

The time had come to go back to my day job in Boulder. N/A was on her trailer pretending to sail a patch of grass at my brother’s property. I hugged her mast and promised I would return soon. She had reached her full potential and proved to be the best adventure partner ever. I tucked her under a large plastic tarp and wished her sweet dreams.