As a refresher, the big picture of what we are doing is sailing from Florida to the Caribbean. There is more than one way to do this, but the one we’ve chosen is known as “The Thorny Path to Windward”. It’s essentially 1,200+ miles of beating directly into the wind, which is not fun to do in a sailboat. It requires lots of planning, lots of waiting, and some tenacity. We had finally arrived at the most notorious stretch of the Thorny Path: The Mona Passage.
The Mona Passage stretches between the Dominican Republic and Puerto Rico, and there has been a lot written about it. We were glued to the weather for several days. Bruce Van Sant, the author of the go-to book on this passage says that the weather patterns periodically switch back and forth like a cat’s tail. You wait for that slack moment where the wind is shifting and is below 15 knots. Then you make the crossing. It looked like our weather window was opening Sunday night and Monday, which was just what we needed to shoot across to Puerto Rico.
We notified the Puerto Bahia harbormaster that we would be leaving Sunday at 6:00 p.m. He assured us that this was ”no problema.” Customs and Immigration and the Commandante from the Dominican Navy would come to give us “un despacho” (a dispatch). You have to have one of these for every port in the DR that you enter and exit, and the DR is very serious about it. They also inspect your boat to make sure you don’t have any stowaways or contraband. I reminded him again early Sunday of our impending departure, and the harbormaster assured me they would all be there around 5:00 or 5:30 to check us out. For fun, I asked him “¿Que pasa si alguien no viene?” (What happens if someone is a no show?). His answer was immediate and serious – “Todos estaran aqui.” (Everyone will be here). Well, the lady from immigration did show up as promised and stamped our passports, but then we figured out that no one could get the Navy Commandante to answer his phone. I asked what we should do, and the universal answer was, “You’ll just have to wait.” So we did… until everyone agreed that the Commandante was not coming Sunday night. The harbormaster went home. The immigration official went home. It looked like we were stranded…
Negative, Star Command. We’ve been planning and waiting for over a week for this, and our weather window is here! We have absolutely no idea when the next window will be open. It’s time to be moving on. One person, whom I shall not identify, told me “Es muy ilegal, pero si el Comandante no está aquí después de las seis, ¡vayan con Dios!” (“It’s quite illegal, but if the Commandante isn’t here after six o’clock, Godspeed to you.”). At six-fifteen, we left.
Now, sneaking out of the country was not as trivial as one might think. For starters, the dock hands had secured our boat with a whopping nine dock lines when we arrived (four is a typical number). These spidered out in every conceivable direction, and no one was around to help release them, so we had to untie a line, keep the boat in position, untie another line, maneuver the boat just a bit to relieve the tension, etc for several minutes. We couldn’t reach some of them without a long boat hook. We high-fived each other when we were finally free.
We got underway and started the long trip to Puerto Rico, planning for 30 straight hours of sailing. The first ten hours or so you hug the north and west coast of the DR so that the night lees (cooling winds coming from shore) help you. The next 20 hours would be crossing open ocean. On long passages, we generally take three or four hour shifts where one takes the helm while one sleeps or rests. But about an hour into our trip, we were both at the helm when we saw a power boat speeding toward us on our port flank.
Then it changed its angle to intercept us.
Oh boy.
The pilot stepped out to the side and motioned for us to stop. It looked like it was time for a reckoning for our misdeeds. We were both very tense.
But it wasn’t the Navy! Two friends we had made in the marina, Nelson and Ramon, saw us leaving and wanted to wish us goodbye and a good trip. Ramon had taken to coming over in the mornings to have coffee with me. It was a good chance to practice Dominican Spanish, which can sometimes seem like its own language.
It took some time for my adrenaline level to come down. I was certain the Navy was after us for skipping town. (We’d heard stories – they will straight-up run you down for trying to leave without a dispatch and will make you turn back, earning you a hefty fine and the ringing of the shame bell).
We made it to Punta Macao, still on the coast of the DR, just before 5:00 a.m. That is where sailors traversing the Mona Passage traditionally make their “go/no go” decision for the crossing. If the weather or the seas are too rough, you simply hole up here or sail a bit further south to Punta Cana to hang out and wait for better conditions. We decided everything looked good (not great) to continue to Puerto Rico. Besides, we were eager to put some distance between us and the Dominican Navy, so we turned east-southeast and headed across 100 nautical miles of open water for the western edge of Puerto Rico.
The wind was blowing strong from the direction we were headed, but it gave us just enough of an angle to use the sails. We raised the main and unfurled the jib, and Gratitude sat up and took notice! She took off, making better than eight knots most of the trip. This put us comfortably ahead of our planned schedule. As first light broke, I ran fishing lines out port and starboard, and just after sunrise, we paralleled a long weed line and saw birds flying excitedly over the water. That is a good sign that there might be a big fish nearby, and just like that, I heard an excited lure strike on the port side, and line started spooling out… fast! I ran over and adjusted the drag to start tiring him out. I had a fight on my hands. Then the fish burst straight up out of the water and shook its tail. This was no barracuda; it was a big mahi mahi!

My adrenaline was going once again. By now, Karen and I have a whole coordinated routine when we hook a fish:
• Put engines in neutral (to slow the boat and so the line doesn’t get tangled in the propellor)
• Adjust the drag on the reel to begin tiring the fish out
• Get the gaff hook and fish billy close by
• Get the pliers handy to dehook the fish
• Disconnect the lifelines that prevent you from falling in the water so you can properly do battle
• Get the fillet knife and cutting board ready
• Ice the cooler in anticipation
• Fight the fish
This mahi shot under the boat and did its best to remain there, but I stayed with it and tired it out and maneuvered it back where I could see it. I brought it up to the sugar scoop (the back step of the boat), and just when I reached to grab the leader, his fin nicked the line, and everything was over as suddenly as it started. This mahi escaped to fight another day and took a very good lure with it.
I should have used the gaff.
I will admit I was very unpleasant company for the next hour, but I licked my wounds, rigged both lines again, and ran them out. The only fish I caught the rest of the day was a small tuna a little bigger than my hand, which I promptly released.
Shortly after that, something got wrapped around the starboard propeller. I stopped the boat and dove in to see what was going on, but the waves were just too rough to do anything useful. It looked like fishing line, and I was able to cut some of it off, but I had to get back aboard before I could get most of it.
A couple of hours later, we were making great time into the wind when I heard a very loud “bang!” from somewhere above me. When I looked up, I saw that the main sail had gone noticeably slack, and we quickly worked to determine what had happened. As it turns out, one of the knots we had tied when we put the sailbag back on had come loose. This one is the outhaul line, which connects the back foot of the sail, known as the clew, to the boom. It keeps proper vertical tension on the sail, which is necessary for the sail to work, and when the sail is up, this line comes under a lot of strain. We both climbed on top of the cockpit and did our best to retie while we were underway (no small feat), and the boat picked up speed and was happy once again.
About 4:00 p.m., we were approaching the western edge of Puerto Rico, but there was one more challenge to face. The last big difficulty sailors deal with in the Mona Passage is the thunderstorms that roll off of the western coast and into the Mona Passage every afternoon and evening. They spit off in rapid succession, and some of them get quite nasty. This is a daily occurrence, and it presents a real hazard to mariners. In Van Sant’s aforementioned book, he says that the worst weather he has encountered anywhere in the world has been right there, including the Mediterranean and the notorious North Sea. We had read about this, but it’s really something to experience. It reminded me of the last level of a video game where everything gets super-intense. We powered up our radar (what a really cool piece of equipment, BTW), which located and displayed the dimensions of each of the storm cells, and we did our best to determine which way they were moving and to thread our way through and around them. We made it through the gauntlet with only a slight bit of rain.

We anchored at Puerto Real around 8:00 p.m. It’s already dark at that hour at this latitude.
Ultimately, we made the Mona Passage in 26 hours, which is great time. The first 13 hours of the passage were pretty bouncy and rough, but the next 13 were more comfortable. (Thank you, weather window!) We anchored at Puerto Real and it was as calm and serene an anchorage as you could hope for. A quick call to US Customs Border Protection using their app, and we were properly back in the USA.


Although we were tired, and Puerto Rico is beautiful, on Tuesday and Wednesday, we continued east. Each day got up stinkin’ early and sailed/motored about ten hours. We had to tack (zig zag) with the wind to get the right angle to sail, but by Wednesday, we were almost to the east coast of Puerto Rico – about 80 miles. This was very good progress. Thursday, we turned and headed north along the coast to the marina at Puerto del Rey in Fajardo, getting caught in a series of storms (squalls) that lasted for hours and played havoc with the wind. It made this leg of the trip a real challenge. But now we have great positioning to make the short hop east to the US Virgin Islands, with a few days to spare for some provisioning (Costco!), boat maintenance, and rest, Puerto-Rico-style.

And one final note, from Karen: WE DID IT! The Thorny Path is a tough route. Many sailors in the U.S. never go farther south than the Bahamas. We were intimidated by the distance and the stories we’d heard… but we decided it was worth a try, and now we’re so glad we did. Virgin Islands, here we come!