3 April 2022: My Most DREADED Passage


3 April 2022

Departure point

Big Sand Cay, Turks & Caicos Islands

arrival point

Luperon, Dominican Republic

distance (NM)

86 NM

Cumulative Mileage (NM)

2,447 NM

Crew on Board


Skipper, first mate, chef, entertainment and more; I guess that is solo sailing for you!



Between 12 and 15 knots


Not a cloud in sight!


Balmy for this time of year


Dry, thank goodness!


I tried to sleep as much of the day as I could before departure to both save my energy generally for an overnighter and because I still was not feeling well.     I had been messaging Jamie on the Garmin regarding weather and planning and had let him know I was unwell and that a multi-day jump to Samana was maybe not an option, much to my dismay.   

I had been (nearly) desperately trying to avoid Luperon and the North Coast of the Dominican Republic by heading straight to Samana (the worst stop of the ‘thorny path’ in my limited experience and amateur opinion).   And I had put so much effort into staying north while getting as far east as I could before jumping south, it seemed a shame to waste that effort by now going almost due south to Luperon.    But, not only was I feeling unwell, the weather window was not incredibly long or ideal (and my week long Turks and Caicos visa had run out), so it was time to jump.  All things pointed to just getting to Luperon and then routing from there. 

Jamie’s advice was to leave around 7pm, it was only around 80 nautical miles so that meant I would likely arrive before sundown the next day.   As the day progressed, I was starting to feel better (or less bad) so I figured all would be alright for a single overnighter.  Around 4pm I popped my head up to see that Troubleshooter had anchored next to me, quite close, so I shouted hello!   I noticed they were wet and commented on it and then said that I had to jump in because if you held your head underwater you could hear the whales singing! 

I took no convincing (and conveniently when I feel ill, swimming tends to make me feel better) and prepared to use my boarding ladder for the first time.   I was no longer worried about getting stranded off my boat as I would just swim over and get help from Troubleshooter if I had any issues.   I jumped in and though there was nothing to see but beautiful white sand all around in every direction, they were right, you could 

absolutely hear an orchestra of whales.   It sounded like a mix of a harmonica and kazoo. 

After a brief swim and fresh water rinse, I felt much better for my sail and had some dinner before pulling anchor and departing.   Bloody Jason on Troubleshooter had dropped their anchor quite close to me and had settled back over my anchor so I had to bug them to pull up a bit so that I would avoid hitting them as I pulled up my ground tackle.   I genuinely think I would have hit them if they had not moved forward to let me out!   Writing this is a great reminder to not forget to harass Jason about such an amateur move when choosing their anchoring spot (despite the fact him and Savannah are substantially more experienced than I am).   Good to have ammunition as Jason loves to harass me (Savannah is way too nice to do any such thing and Vera too young)!   They were becoming great buddies though as I continued to really enjoy their company at every stop.

As I departed, I got underway in the annoying washing machine kind of swell.  Conditions that required motor sailing.   But despite having the dinghy up on the davits and well secured to minimize the jerking motion, the nose of the dinghy jerked free as the ring connecting the davit ripped out of the attachment point that held it up.   With the rear of the dinghy still held aloft, the nose of the dinghy was bouncing and dragging in the sloppy sea conditions.   I was worried more damage would be done if I did not get it sorted. 

First, however, I remembered Jamie’s advice to not cause other problems and escalate a situation by carelessly rushing to solve something.  So, initially, I made sure my heading was correct and I was not aiming for land and my sails were set.    I ran through in my mind things that would make this situation worse.  The only things that I could really think of was me reaching far enough that I fall overboard or getting a line stuck in the propeller or wrapped around the rudder.  Therefore, I made a mental note to not push it too far trying to fix it and instead risk the dinghy instead of myself falling overboard.  I also made a note of the situation with the lines.  Which ones were tied and what was or might be dragging if I was not careful. 

I put on my tether and went forward to grab my boat hook.   My trouble was that I could not reach the other attachment points with the dinghy dragging so far down, even with the boat hook.  However, luckily I had two lines tied to the dinghy for tying up at docks (one long and unwieldy for crowded docks and one shorter one for most of the time).   The short one was used to keep the dinghy close to the boat in the way it was previously tied before the nose fell.  I figured undoing that would just cause more chaos as that was at least keeping the nose of the dinghy still near me.  But the other line was coiled and sort of tangled in the dinghy.  Getting that line was likely my only option to better secure the dinghy.

I remember at this point being annoyed that it was so dark and sloppy out.  It sure made everything more difficult.

After what felt like twenty minutes with the boat hook, it felt like twenty minutes but I cannot confirm how long it actually was, I got the line free and in my hands without dragging it in the water and risking the rudder and propeller issue I was worried about.   And it was a simple controlled lean to toss part of it over the dinghy davit and bring it back to myself with the boat hook.   I pulled it up and tied it to the railing.   I also attached the davit line, now freely swinging to an attachment point on the side of the dinghy as a backup.  This made the dinghy a little lopsided, but it was better than worrying about it swinging excessively and it was reassuring to have a backup attachment point.  

Once I was happy with it, I reverted back to sailing and just prayed it did not cause any more drama for the rest of the trip.   I could not think of a way to currently make it any better.

On a positive note, I was soon out of the washing machine type sea state near the islands and reefs and was in the open where it was much calmer.   By this point it was maybe nine o’clock and I could see on my AIS that Troubleshooter was on the move from the anchorage at Big Sand Cay and that Pianissimo was in range too from their direct departure from Cockburn Harbour.   However, it was not long and I had left them in the dust (likely because they were still slogging through the washing machine-like conditions and I free of it to dash south). 

I got my wish as there was nothing eventful throughout the night and the next day.   I did get to relive the best part about arriving to the Dominican Republic: seeing hills and greenery for the first time in months and smelling the sweet smell of dirt (the sea is the Bahamas is stunning, but the land is very barren and desolate and uninspiring).  

I arrived to the Luperon harbour entrance around 3pm and radioed to the local harbour host from Seven Seas Cruising Association (SV Fair Lady).     They gave me directions to the anchorage and messaged the Armada for me to get checked into the country. 

I anchored close to the dinghy dock as I love a short easy dinghy ride and made sure to stay away from the mangroves to avoid the bugs at night!

It was not long before the Armada came out.  Two men, an English speaking interpreter named Richard and one of the Armada who did not really speak at all, boarded the boat.   It is known to make sure to have a cold beverage waiting for them and all I had was grapefruit juice (I had been saving it for myself as a treat but it was a large one so I offered them some).    They both drank a glass and had seconds and then asked for cookies.   I did not have cookies but did have a granola bar so I offered them each one.   I was sure surprised when they requested a second granola bar (those things keep me going when I am solo sailing and do not feel up to food prep underway so I was a little annoyed).   But they did not inspect my boat – there is nothing to find, but I just did not want the hassle of opening cupboards and rifling through everything – so I guess I cannot complain about the juice and granola bars too much. 

As Richard said, “I look at your face and in your eyes and know that we do not need to look at anything here”.   I suspect the real truth is more like, “we got our granola bars and juice, so we cool”.  

Now I had been “inspected” I was allowed ashore, but I would have to do the rest of the paperwork (customs and immigration) the next day since it was after 4pm by this point.  So I jumped in my dinghy and went into town to North Bar, a restaurant newly opened by some friends of mine from Canada (Jenn and Dan, the only reason I was happy to come to Luperon).   I had a Peanut Butter and Maple Syrup burger, which was incredible, and a watermelon margarita that Jenn made me as a welcome to Luperon.  I ordered a second margarita because my lovely Patron, Shane, wanted to celebrate my arrival to the Dominican with me and had ‘bought me a drink’ from my Paypal link.    

I did not realise how strong these margaritas were until after I had already consumed two!

It was great to see familiar faces and I was ecstatic at the price of food in town.  The burger only cost me $8 USD with the most delicious homemade french fries on the side.

I was already feeling positive about the week or so I would be spending in Luperon which was a nice change to my expectations and memories of the place.   Why such terrible memories of the place, you ask? 


Firstly, I was dreading the sail there due to my last time being a rough ride.   In 2019, you can see on the map for One-O-Six that we took three days of slogging upwind against the current from Great Inagua, Bahamas to Luperon.   We broke our furling line, had leaky chainplates, wrecked laptops and much more.   Upon arrival we grabbed a mooring in the dark.  Exhausted, we backed down on it to check it was secure.   Waking up to move the next morning only to find out that we had no propeller.   It is a long story but it was mixed feelings as to whether or not it was stolen somehow as there were a few signs that it did not just fall off (the main one being that we had inspected it before our departure in the Bahamas and the key slotted in the groove of the propeller shaft was still there, not sheared).    So my impressions of the place was not only that it was rough to get to but also, I thought, annoying to fix anything in such a small town.   There was one used parts store and fresh food and not much else. 

Aside from being smack in the middle of the thorny path, I particularly disliked Luperon as a town on my last visit.   The harbour is incredibly dirty, you would never swim.  The town streets are also very dirty and also the run off on the streets all runs into the harbour, only further confirming your commitment to refusing to swim (and let me tell you, the only reason I put up with the efforts of sailing and maintaining a boat is seeing beautiful places and swimming off the back of my boat any time I want so this place was really not for me).  The cruiser scene was also very odd, consisting mostly people who stopped in Luperon and never left.  Some of them living on their boat in that dirty harbour for over five years or eight years or ten years (it was not uncommon to hear this story).

This time around, though I still felt a similar feeling, I had a little more hope about giving the place another chance.   After all, impressions could hardly be worse than the last time around.  Though I still hoped not to stay long.  Getting east is my sole focus and priority!

But at least the most dreaded leg of my American and Caribbean sailing went down essentially without a hitch!   It just goes to show how important good weather routing and patience is for comfort!        

“The more humble a person is, the freer and stronger he is.”

 – Leo Tolstoy

2 Responses

  1. Sounds like your memories of Luperon have been at least somewhat improved, Glad to hear that!
    That “Shane” character sounds like a nice guy, but beware of the Watermelon Margaritas!! ;-)

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