Life aboard Tamarisk is a lot like a heroin habit (we assume) – the highs are epic, but so are the lows when they come around. For us the lows always have the same root cause, one that was largely unexpected when we first thought of this trip over a year ago. Our curse is mechanical and electrical problems that never seem to end. As we hop along the mostly undeveloped southern coast of Cuba on our way towards Jamaica, we again face mechanical problems that will force us to make some tough decisions over the next few days.

Our list of problems is annoyingly similar to the one we entered Florida with almost three months ago. Our brand new autopilot hydraulic literally exploded a few days ago, sending hydraulic fluid everywhere, and forcing us to take the helm for 3 hours in 30+ knot winds, struggling to reach the Cuban coast for shelter. Our house battery bank refuses to hold a charge, the cause being either our new charging system or the new batteries themselves. Our new mainsail appears incapable of holding its battens (supports) thanks to the sailmaker’s idiotic decision to use cheap plastic batten holders designed for a 33’ to 50’ boat… if we were married to North Sails we’d be filing for divorce today. With a list of problems like this, and no good services before the Pacific crossing, we need a miracle to occur in Jamaica, or we’re heading back up to Florida next week.

The problem with another unplanned Florida detour (in addition to the repair costs) is now the weather. The tropical storm season in the Caribbean begins in late May and ends in November, and a passage across the Caribbean Sea is to be avoided during these months. Our detour to Florida will almost certainly give us a June departure, meaning we’ll be too late to make it to the Panama Canal this season. That would be a devastating blow to our plans, our response to which is still unclear… we’re trying not to think of that just yet.

For now, we face howling winds each night as the season begins to change and the weather becomes more disruptive and unpredictable. Without our primary autopilot or a properly functioning mainsail, our ability to sail through nights like these is limited, so we’re tucking into hidden coves where we can sleep in peace. Our progress towards Jamaica is thus slower than we’d like, but on the bright side, we’re exploring some of the most remote isolated bays we’ve been to yet, and the fishing here is like nothing we’ve experienced before. So as we’re cooking up some of Swifty’s 100+ pound (he claims) Yellow Fin Tuna (probably will be closer to 200 by the time he gets home), we’ll be thankful that our downer days are like this (probably better than a heroin habit).

By far the most interesting thing about Cuba for us has been seeing how life works in a truly communist place that still subscribes to the utopian socialist ideas of Karl Marx. Since the fall of the Soviet Union, examples of places still experimenting with these ideas have become difficult to find Most people who’ve read the Communist Manifesto would probably agree that the whole scheme sounds deceptively appealing on paper – if we all work together for the benefit of society instead of pursuing our own personal self interests, everybody will benefit. For anyone still holding onto some kind of misguided hope that this concept might actually work in reality, a visit to Cuba should quickly dispatch such thoughts.

We’ve been doing a healthy mix of sailing and exploring the interior of Cuba for the past week. Our passages have been mostly uneventful, mainly because Cuba doesn’t have a whole lot to offer for cruising sailors. Partially this is because of the embargo by the United States, partially its because Cubans aren’t allowed to own boats (they’d simply sail away if they had the means), and partially its because the bureaucracy here still scares off many sailors who generally don’t like filling out hours of paperwork and being subjected to searches each time they arrive or leave any port. It’s also a dangerous place to sail thanks to extensive shallow areas off the southern coast, poor nautical charts (maps), and little in the way of help if you have any problems (we were forced to perform a rescue of a grounded sailboat after Cuban Coast Guard failed to respond to emergency radio calls). Nonetheless we’re making new yachtie friends each place we stop, a task made easy by the fact that so few sailors make it this far from the beaten path.

Ashore we’ve been discussing the situation here with locals and trying to make sense of this bizarre political and economic system that’s difficult to even comprehend for a westerner living in a more capitalistic place. With all means of production owned by the state, the concept of a company doesn’t really exist here. Everything from the restaurants to the gas stations to the grocery stores to the chicken farms to the news outlets to the cell phone provider to the boat marinas to the beer makers… all of it… is owned and run by the government, meaning the entire population is employed by this one gigantic all-powerful entity – the state is everywhere. Regardless of a person’s profession, the pay (and food ration allocation) is roughly equal for everyone, there is no possibility of climbing any sort of economic ladder, and incentives to create and innovate simply don’t exist. For these reasons, the people here have few choices to make – everything in this mostly generic world is decided by the Cuban government and the country is effectively frozen in time. It feels like an experiment gone wrong because, as the fall of Communism in Eastern Europe over 20 years ago clearly demonstrated, that’s exactly what this is. Without the relentless propaganda campaign and strict control (blockade) over all information flow, the people might organize themselves a rebellion. Fortunately for the Castro regime this seems to be a concern for the future, but not for now.

It’s also becoming clear to us as we spend more time exploring the interior that the Cuban people are doing pretty well under the circumstances to circumvent the Marxist rules in pursuit of their own self interests. Capitalism, albeit in some of its least healthy forms, seeps in through the cracks everywhere, meaning there’s an underground market for almost everything. Non-sanctioned taxis undercut state taxi prices by miles. Tobacco farmers sell cigars for a fraction of the price of official “Cohibas” and “Monte Cristos”. A midnight trip to Key West aboard a 1000 horespower black cigarette boat can be bought for $10,000. Prostitution is so rampant here that a group of three visiting western guys could be forgiven, in our opinion, for presuming most youthful Cuban women to be prostitutes until proven otherwise.

It’s our last night in Cuba before heading south towards Jamaica. The Mahi Mahi is now defrosted because we’ve invited our new Swedish friends Ola and Caroline over for dinner on the boat tonight, then we’re all off for some entertainment at the local (state run of course) Karaoke joint…. and here they are “yoo hooing” on our back deck now, so gotta run.

By western standards, Cuba is a failure in many ways. Good employment is impossible to find thanks to a dysfunctional communist government, the country’s infrastructure is crumbling, the standard of living is generally low, progress is non-existent and there’s little hope for meaningful improvement. Freedoms here are very limited, information flow is strictly controlled, the Internet barely even exists, government propaganda is everywhere. Cuba also appears on the US’s short list of “state sponsors of terrorism” (don’t ask us why), its influence over world affairs is limited, the country slowly drifts towards obscurity. But failure by western standards is different from outright failure, and despite its many shortcomings, the lesson we’ve been learning over the past few days is that the Cuban people are making the very most out of what they have.

If instead of material measures of success we use more human yardsticks like happiness, generosity, friendliness, and willingness to help others, Cuba might actually deserve a medal. It’s a good thing we’re working with a $0 embargo-compliant budget which makes the touristic places off limits to us, meaning we’re forced to go out of our natural comfort zone and are doing our best to blend in with the locals in a chameleon-like way, and that’s why we’re learning some great things about the Cuban people.

Normally if you’re having a karaoke party with your friends in your own second-floor apartment and some random tourists come climbing up the stairs and start peeking through your front door, a normal reaction might be to tell them to get lost and possibly think about calling the cops. Not so here in Havana. The moment they saw our three curious faces peeking into their apartment door, they smiled, grabbed our arms, pulled us inside, poured us drinks, began singing American songs, put microphones in our faces, and moved the chairs aside to make room for a living room dance floor. What followed were two of the most crazy and hilarious hours we’ve had since setting sail from Marmaris last year. With the night still young, we walked down to the sea wall where locals (and only locals) congregate on weekend nights. This is where our night started going pear shaped… as the locals noticed we were out of place, large numbers of them went way beyond the call of duty to make us feel welcome, and by that I mean free flowing Havana Club rum and so many invitations to parties that we ultimately had to run away so we could preserve our plans for exploring further afield the following morning. We’re still not sure if leaving the sea wall that night was the right choice.

We woke up with headaches the next morning but still managed our way out to the very scenic Vinalis tobacco field area in the western part of Cuba where we found more smiling faces welcoming us there. The farmers would stop their work to answer questions, smile for pics, give us directions, show us to hidden waterfalls and even pour us some of their locally grown coffee and coconut milk. We don’t know what it is that makes the people here the friendliest and kindest we can remember meeting anywhere, but whatever the reason, this is what we’ll remember most about Cuba.

It’s time now for us to sail away from Havana, around the western tip, and begin making progress eastward along the more sparsely populated southern Cuban coast. Our Croatian friends on the boat next door tell us it should take around five days to sail to Cienfuegos, meaning we’ll probably need to break things up with a night or two on the anchor along the way.

It was a long awaited joy to sail out of Fort Lauderdale after nine weeks of working on the boat. After leaving the harbor we soon found ourselves in steady 25-30 knot winds with a powerful Gulf Stream current pushing against us. At times we had 9 knots of speed through the water, but only 5 knots over ground. The combination of high winds and choppy sea state was a great final test for our new sails and autopilot system, all of which performed flawlessly.

Our first destination after leaving the US is Havana, Cuba. Due to the ongoing US embargo of Cuba, this is a challenging place for most Americans to visit. If we were an American flagged boat our passage to Cuba would be illegal, and even though two of us are British citizens (in addition to American), we are subject to the US laws prohibiting US citizens from transacting any business in Cuba, which means we can’t spend a dime (or peso) here. Fortunately for us, we’re here with Canadian friends and a kind group of yachties who aren’t subject to these rules and who are more than happy to show us around and cover the few unavoidable expenses that may or may not arise… and that’s all we have to say about that.

So here we are just 90 miles south of Florida exploring one of the most bizarre places we’ve ever been, and having the first truly communist experience we’ve ever had. The four hour entry formalities were nothing shy of astonishing as officials from multiple government agencies boarded and searched our boat, completed a thick pile of paperwork, sealed our radios and navigation equipment, and confiscated our emergency flares (the goal is to ensure none of this equipment, or anything else that might be useful in planning a revolution, gets into the hands of the people).

We then hitched a ride to Havana Vieja (the old town) which is where things get very interesting. Havana is famous for its unusual mix of historic cars, many of which are classic American cars from the pre-embargo years, and others are Russian built from the times when Cuba and Russia were close allies. The block-like architecture and vast open spaces are typical of communist and former communist countries. What makes Havana different from other places built under communist regimes is the bright colored architecture and prominent artistic influences – the sights here are unlike anything we’ve seen or heard about anywhere in the world.

Walking around Havana is something that must be experienced to be fully understood. We were hustled constantly by street peddlers, trinket vendors, restaurant solicitors, marijuana sellers, prostitutes, and pimps…. a sucker and his money here will soon be parted. Once you master the art of saying “no”, or just ignoring the hustler chaos, and start enjoying the stunning sights and vibrant life, the place is suddenly becomes truly fascinating.

There’s lots more to say about this unique place, but for now we need to get ready for our Saturday night out in Havana, we’ve promised to make it a memorable one (as much as US 31 CFR 515 will allow anyway).