Authors note: A lot has happened in a short time so please forgive me if this ends up being a very long post.

Dani and I had been watching the weather since around the middle of our second week in Key West. Though we found the city charming it was still undeniably American in every sort of way that a tourist town can or could be, and I think we both longed for more. So each day we’d use some of dwindling time we had left on our cell phones or tapped into the internet and look at what the weather was going to tell us to do. As it turned out, the weather agreed that after just about two weeks it was going to be time for us to make our way out into the larger world and away from our home shores. It was time for us to take our first baby steps into the International world.

We were both filled with a mix of excitement and fear. Much like leaving the dock at home, there was so much anticipation born of ignorance and hopes. How would clearing into another country go? Would we be able to communicate? etc. To a lesser extent the thought of crossing the gulf stream for the first time was decidedly unsettling after all the stories I’d heard about it. Though I am totally new at weather routing, I decided that perhaps for some limited period of “beginner’s luck” I could trust myself and so we set the hard date that we would up anchor and simply sail out of Key West and out of the United States. The day before we hoisted in the porta-bote and folded it up on deck, made the boat ready for sea, and went to bed. The next day there was no drama in raising the anchor out of the clean waters and getting underway. It seemed like just yesterday that we’d sailed in and as soon as the water began lapping at the hull I had a sense of deja vu.

The forecasts that I’d been following had called for a northerly wind at 10-15kts and then the wind would clock to the East overnight and into the next day, giving us a beam reach (our best point of sail) but not so good because it would also run counter to the current of the Gulf Stream. The Gulf Stream is a powerful warm current that passes between Cuba and Florida before heading up the East US coast. If the wind and the current disagree on direction it can cause some very large waves very quickly. But once out on the water I just had to trust my planning. We watched the water change from the aquamarine green of Key West into a the deep blue of the open ocean in a very short period of time. We sat back and engaged the windvane, both too lazy to drive.

Passage to Havana

The first hitch of the journey south happened when the predicted 10-15kt winds ended up being 5-10kt winds. The wind just sort of slowly died off and pretty soon the waves were pushing us around and we didn’t have enough power to make way at more than a knot or maybe two. It was pretty crappy. So we fiddled with poling out the jib to go downwind but it wasn’t enough so finally I looked over at Dani and said, “Hey, do you know where the spinnaker is?” It seems incredible now, but we’d never flown our spinnaker. Every time we’d tried to sail and fly it, the weather had not cooperated. But here we are in 1000ft of water off Key West and the wind dies. So Dani dug it out of the Vberth and I rigged it up, somewhat worried if I was making a mistake. For you non-sailors out there, the spinnaker is the BIG sail with lots of force and a LOT can go wrong. For you sailors, our spinnaker is a asymmetrical w/ a sock so it is pretty easy to handle. In any event, we got it hoisted and bang! It filled and Sundowner immediately gained an addition 1.5kts of speed.


Still, we were going slow though. We had taken the windvane off of steering duty while changing the sail. When we rengaged the windvane we picked up another knot! It can steer a course better to the wind than we can and thus kept the sail more filled and so we were off to the races, slowly puttering along south-south-west. We enjoyed the peaceful and beautiful sunset and Dani retired to off-watch status to try to sleep while I stayed on watch with my book.

Passage to Havana
Sometime in the night, probably around 9pm I started tracking the navigation lights of a vessel off in the distance that wasn’t appearing on AIS. Being that we were in the straits of Florida I immediately assumed it was either a USCG boat or a naval vessel. I watched it for a half hour and it seemed to be going the other way so I went back to my book. Sometime past 11pm though I was startled by the handheld VHF radio in my lap hailing the sailing vessel that had our GPS coordinates. It was the USCG. I woke Dani up as the coast guard cutter flipped his flashing blue lights on and began approaching. Ready for the worst we had a short conversation in which I was asked if I was alright, where I had come from, and where I was going. In the end they wished me well and we continued on. But what a rush to be woken up to that in the middle of the night. But the night had more in store for us.

As my watch dwindled down the wind picked up. The temperature suddenly changed and I began to suspect we’d made it into the gulf stream. The waves increased and while I believe the spinnaker sail would have been alright, the waves would cause the boat to roll so much that it would change the wind angles and the sail would collapse and then when the boat rolled the other way it would fill again with a tremendous BANG that would reverberate through the entire boat. So I got Dani back up on deck and in the full moon light ventured out onto the foredeck to take down the spinnaker using its snuffing sock and hoist the genoa sail once more. This sounds easier than it is. Clipped in you cannot get around very easily and the boat is rolling back and forth while rising and falling. The seas were around 8ft at this time, but at least the moon gave me good light to work in. The snuffing sock is a huge sock that you pull down over the sail which closes it. This was pretty hard with all the force of the wind keeping it filled. Then I had to lower the spinnaker, go to the mast and raise the jib. It took about 15 minutes. By the end I was totally exhausted. Dani and I engaged the windvane and I went below to rest.

Twice in the night I had to be woken up to deal with situations (Just like Dani had been). These situations arise when a large ship is going to pass too close or if we see something we can’t identify. Luckily, the ships that were passing “too close” were also responsive on the radio and both of them courteously altered course for us so that we didn’t have to make sail or course adjustments. We just keep on chugging along through the gulf stream.

I relieved Dani in the morning. She too was exhausted by her watch. Neither of us got much sleep that night/day. Dani confessed to me later that she was actually getting to the point of “seeing things that weren’t there” like imagining a cargo ship. That is what rough seas (adrenaline) and tired eyes can do to a person. As the early morning hours wore on the winds did clock around fully to the east as promised and this caused the seas to really pick up. At one point I believe we may have seen a few 12ft waves. Mostly though it was more 8ish footers. Not the most comfortable sailing we’ve ever done but once again our windvane did the yeomans work of steering us true and at the same time we never felt like we were in any danger. Sundowner behaved beautifully.

Though we were slow, slogging along in the current and waves, we did time things just right to make our landfull with the sun high in the sky overhead (which is how you’re supposed to take difficult entrances). And as we approached our destination I was able to realize one of my lifelong dreams. I spotted Havana and though it was cheesy, I whispered to myself, “Land ho.”

It sure looked like a modern city. A big city. But I knew in my gut that beneath the many years of modern building and systematic growth there was old Havana, a bustling semi-ancient place with Cathedrals and with a monstrous fort through which Spain routed treasure ships from South America. Somewhere in that mess was a place that occupied my dreams of pirates, bucaneers, navies, and the Spanish Mane!