Last April in Marmaris as we began our journey, the idea of crossing a large and unwieldy body of water like the Caribbean Sea was not an intimidating thought That was a sign of utter cluelessness, not one of admirable bravery. A year later, thanks mainly to our countless “humblings” in all corners of the Mediterranean and several refresher courses on the Atlantic crossing, we know better, and today we take very seriously any passage across a body of water with the word “Ocean” or “Sea” in its name.

We now enter the third and final ay of our Caribbean Sea crossing with Cartegena, Colombia less than 150 miles from our bow. Over the past couple of weeks we’ve battled against the changing seasons, which forced us to make this crossing before the tropical storm season gets underway, and also against autopilot problems that threatened to create intolerable delays. We were pleased to finally get our autopilot cleared through Jamaican customs and even more pleased to get the installation completed and our passage underway in less than a day. We won’t declare victory on our autopilot problems just yet, but after two days of 20-30 knot winds and the heavy seas that Caribbean Sea is known for, we can at least smell that victory is nearby.

Multi-day passages like this, in our opinion, aren’t a reason to take up the hobby of sailing. For those imagining it to be a relaxing cruise filled with fishing, reading books, and sunbathing on the deck, talk to us about this before buying your dream boat. Even a big boat like Tamarisk gets tossed around like a toy – beginners find it loud, violent, seasick inducing, and with the hatches closed to keep the waves out, its hot enough down below that Swifty calls it a “sweat camp”.

But there’s a reason we endure the heat, the waves, the pounding, etc. and will continue to do so until we’ve gone 360 degrees around the marble and back to where we started from. In a word, it’s our curiosity, and as we approach Cartegena, being a new port, a new country, and a new continent all at once, our anticipation reminds us how curious we are. We’re probably asking ourselves some of the same questions that have driven people to explore far away places since the beginning of time: what might we find, who might we meet, what might me learn. But before we get to any of that business the first thing we’ll be asking is where can we find an ice cold cerveza?

The best thing about a nomadic lifestyle like ours is that we’re constantly meeting some of the most interesting people imaginable from all corners of the globe, all of whom have an extraordinary sense of adventure and very low tolerance for boredom. If you’re in need of some new interesting friends, just show up at some random marina way off the beaten path and see who comes sailing in, or just go walking around the streets nearby and see who you stumble across. This exercise in diversity is not free from risk – the problem is that these people bring new perspectives to your life, they teach you to think differently, and quite quickly you start getting the sense you’ve been wearing blinders your whole life.

On balance we think our new perspectives are a good thing – we find ourselves becoming more interested in other cultures, we shed many of the mental limitations that used to stop us from chasing our dreams, we see there are countless ways to live interesting lives that are very different from the ones we used to live. All these things are liberating and bring a fantastic feeling of richness, freedom, and control. But we’ve also lost a type of bliss (perhaps the ignorance type) we might have had some years ago, which may or may not be a good thing. We see problems in the world, particularly in developing countries, that used to be hidden from our view thanks to our westernized safety bubbles (things like CNN) and we discover we contribute to them – our old sense of national pride and patriotism gradually morphs closer towards a sense of shame. We’ve forever changed our ability to easily remove boredom from our lives – a basketball game, the gym, Starbucks, and a movie would all be futile attempts now. We have interests and opinions that make us peculiar or boring to some people who used to be our friends, and vice versa – some old relationships will never be rekindled. Like many things in life, the changes we experience are a twin edged sword.

We’re now getting ready to leave Jamaica hopefully within the next few days if we can somehow wrestle our autopilot hydraulic away from the kung-fu death grip of the Jamaican customs authorities. In addition to having Desiree aboard for the past week, we’ve also met an unusually large group of new friends here and will be leaving enriched thanks to our experiences with them, and also with some new practical skills under our belt. We know how to run a Jamaican taxi service (thanks to Kiewa), build a solar panel array (thanks to MJSailing), harpoon and land a 200 pound marlin (thanks to the Scandinavians on S/Y Relax), and we even know how to hold our breath underwater for a few minutes (thanks to the world record setting freediving team on Evolve).

Now it’s time to say some final goodbyes as the Swedes strap their dinghy to the deck and embark for the Azores. We hate the goodbye part, but it’s an unavoidable part of life on the high seas and we’ve learned to deal with it by now. So to all of them we say “Bon Voyage”. (And to the Jamaican customs officials we say [expletives deleted].)

The distance between Cuba and Jamaica is barely even 80 miles, but when you travel from one place to the other, it literally feels like you’ve arrived on the other side of the planet. Jamaica is about as far from communism as a society can be, and that’s a refreshing change. Our week so far in Jamaica has been made more interesting than most because of the people we’ve found here. In addition to the unusually large number of young (30-something) sailors we’ve met here, we’ve also connected with Kiewa the Messiah, which is Piers’s Jamaican friend from his last visit some years ago. With this very diverse group, we’ve explored all corners of Jamaica during the past week.

As almost always is the case, we’ve gone far off the beaten path in Jamaica and have been learning about local life here while avoiding anything with a tourist bus out in front. That’s been pretty easy thanks to the time we’ve spent hanging out with Kiewa the Messiah, who’s about as local as a Jamaican can be and, luckily for us, as curious about our lives on the boat as we are about his. Kiewa is a Rasta, which means he subscribes to the beliefs and lifestyle of the Rastafari movement, which is partially a religion and partially a way of life. This means he’s deeply reflective, maintains a simple and humble lifestyle, rejects materialism, accepts everyone, eats a strict vegetarian diet, and like all Rastas, smokes the “sacred herb” (marijuana) in a way that is far more spiritual and religious than recreational…. a nicer, more selfless person would be difficult to find anywhere.

Crime in Jamaica, unfortunately, is a real problem, particularly the petty theft variety, and visiting sailors need to be careful here. We learned about this the hard way the day we arrived when we lost a cell phone to a clever teenage street thief (now in jail after showing off to the wrong people). The growth and consumption of marijuana here, despite its popularity, is all totally illegal and, surprisingly, quite strictly enforced. We’ve already been thoroughly searched several times (one boat boarding and two vehicle searches), and although government searches are always an annoyance wherever we are, the suspicion here is probably more justified than usual given the drug smuggling problems. A confiscated American sailboat sits just 100 yards from our anchor after the owner tried stashing away 400 pounds of the sacred herb last week – a tempting $500k profit if he’d made it all the way to US soil.

Most tourists to Jamaica come by cruise boat or to visit one of the gigantic all-inclusive resorts. This is a shame – their protective bubbles shield them from the hazards of Jamaican street life, and also shield them from almost everything that’s interesting about the place. We’ll probably be here for another week or two while we wait for autopilot parts coming from Miami, then as soon as possible we’ll be heading south to Colombia – a place where the drug smugglers think in $millions, not $thousands. The weather is changing now with storms, torrential rain, and squally winds becoming pretty routine, so we’re anxious to get across the Caribbean Sea before this becomes a more significant threat.