20 March 2022: First SOLO Overnight Sail!


20 March 2022

Departure point

Calabash Bay, Long Island, Bahamas

arrival point

Landrail Point, Crooked Island, Bahamas

distance (NM)

91 NM

Cumulative Mileage (NM)

2,112 NM

Crew on Board


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



14 knots upwind


Ominous looking, but all bark and no bite.


Not too hot, not too cold!


Dry, thank goodness!


Departing the next morning around 11 o’clock, the planned sail was around 85 nautical miles.   By leaving in the morning, it meant no matter what I would be arriving in daylight.  If I was super efficient, I would be arriving first thing in the morning.   But if I was running behind, I still had many hours of daylight before sunset the next day. 

My priorities were to conserve fuel as it was possible the Dominican Republic would be the next time I would be able to fuel up.   So early on when I could not get a good angle on the wind to point at Crooked Island, I did a bit of tacking to get a better angle.   It meant adding a few miles to the trip and pinching close to the wind so that I was only going 3 knots (maybe 3.5 knots) most of the time.  But this was exactly why I planned the extra time to arrive in daylight the next day. 

My goal was to make my first solo overnight as easy on me as possible by getting a good angle before sundown so there was minimal sail adjustments required while I was tired and it was dark.   Therefore, I was happy to tack during daylight.  I envisioned how great it would feel to have an effortless first solo overnighter but that was thrown out the window pretty early on as I heard my bilge pump running constantly from my seat at the helm.   Looking at the spot where the bilge should be pumping overboard and seeing nothing coming out and I knew that something was off. 

It was normal for my bilge sensor to be submerged when I was on a heel and the actual pump to be above water, so my normal tactic was just to move the sensor a little higher and so it was at the same level or slightly above the pump.   That ensures when the sensor is set off, there is water for the pump to pump.   However, I opened the bilge compartment and the stench of diesel fuel hit my nose and the sight of pure black oil met my eyes. 

My brain immediately returned to the oil change earlier in George Town and the oil that always leaks when I do a quick swap of the filter (which lays on its side).   However, I usually put down paper towel to try and catch that oil and I had done oil changes before without this issue so I was surprised to see it in the bilge now.    As for the diesel smell, I had not yet had time to process what might be happening there. 

I used my pump for changing oil to pump everything out of the bilge and into a container and mopped it dry with rags.    You will notice on the map of my travels the last tack over Long Island leading me the furthest north (and clearly not trying as hard to pinch towards the North East) was actually the wheel pilot driving while I was below pumping and cleaning, just occasionally popping my head up to ensure there were not boats to worry about and that the sails were still sweet.   As soon as I was done and washed up, I tacked back south and found myself on a good angle to head directly to my destination with the wind.  

A minor hiccup that I hoped would be the worst thing to happen on this initial overnighter. 

And it was, though I could see the issue returning as the bilge filled up again, it did not seem to affect anything.  The oil levels were the same in the engine, the diesel tank was still reading as full.   And pondering it all while sailing, I decided that it must have been the leaked oil on filter change and possibly overfilling the diesel when not paying enough attention while siphoning on my George Town fill up.   I decided to sort it out on arrival to Crooked the next day and started preparing for the overnight portion of my sail.   

Shortly after the oil incident I got quite a bit ahead of buddy boat Pianissimo as they could not point as well upwind as I could with their shallower draft, full keel.     We ended up out of radio and AIS range.   However, we had not talked as buddy boats if the plan was just to make sure the other arrived safely or to literally stay together.   But in that moment I decided the safest thing for me was to spend less time at sea and be exposed to less weather, they would have a boat waiting for them at anchor ensuring they arrived.   There was no point having a boat close by if the skipper was exhausted and mentally drained.  I also had their Garmin link so that I could see how they were going once I had reception at Crooked.  

And so I carried on. 

I started my periodic napping very early in the evening as I find it harder to catch up once I am tired than to prevent tiredness in the first place.  

So though I was not sleeping at first, I was at the least resting my eyelids in 20 minute increments.   Because I had a fabulous dodger and connector to the bimini, my cockpit is very dry.   So I had a good pillow and blanket, I had my alarm on my phone connected to the Bluetooth surround speakers to ensure that I did not miss it and set for regular 20 minute intervals.   I would rest, usually stir before the alarm, check the charts and AIS transmitted from other boats (if any nearby) on my tablet while still laying down.   Then I would hop up (amble up more like it) and check the compass to ensure I was on course, make sure I was happy with my speed, look at the sails and the wind angle (with my anchor light on to light it up because the electronics were still not working), scan 360 degrees around me for obstacles or other vessel lights and check the radar for squalls and other vessels. 

Then I would take my next 20 minute nap and repeat the cycle. 

My efforts overnight were rewarded with a brilliant sunset, incredible stars, perfect sailing weather and a welcome sunrise.   There was a few other boats headed the same way and we would usually make radio contact as they passed by (many other boats happy to motor sail everywhere as needed meant they moved faster).   One boat that had just gotten ahead of me and realised I was solo sailing, radioed back to tell me about a little rain squall coming.   They said they did not need to adjust their sails, it was really just rain.  So I put away my blanket and pillow for a half an hour or so until it passed and then resumed my sleep/wake routine.  I made good time on this last half of the sail and arrived in time to have breakfast at anchor.  There were no major incidents and I was not insanely tired.   In fact, if I did not have a buddy boat trailing behind me I might have been tempted to carry on weather permitting.

I had concerns over my buddy boat as they were really, really far behind me.  So, throughout the day I kept an eye on them from their Garmin map link.  They arrived almost ten hours after me and arrived with tales of a harrowing sail.   My motivation to arrive early was driven by the weather, so after I dropped anchor they faced a couple of big squalls.   They lost a water jug of their toerail where it was lashed in one squall (retrieved in the end), were dropping and raising sails due to squalls after daybreak and the choppy seas caused a plastic plate to fall on and melt to the stove while making coffee.  And that is only the chaotic stories that I can remember!  

I felt for them as they had a long sail with no autopilot at all and, given they were on a ketch rig with an extra mast and different sail plan, I had no idea how to share the useful information with them that I had learned about balancing my sails.  I was sure their sail trimming was different and I was no expert on my own boat let alone on another kind of boat. 

Feeling proud of myself for a big accomplishment, I took a couple of naps and checked in on buddies on Pianissimo – Scott and Roxanne – and then joined one of the other boats for a birthday celebration on the beach.   Why not have a little bit of cake and a visit with other cruisers as a treat after a job well done!

“A little progress each day adds up to big results.”

 – Satya Nani

2 Responses

    1. It felt like such a big accomplishment!! Thank you! … (though in some ways it is a chore, because now I know I can do them they can be planned in to make some miles; but they do zap my energy so I really need to brace myself before taking one on).

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