Rolex Middle Sea Race Break Down

Rolex Middle Sea Race

Rolex Middle Sea Race Break Down

For those of you who watched on during the 2019 Middle Sea Race, you will have seen that Challenger did not have a competitive race after the first 48hrs.  It was a situation that came upon those on board unexpectedly despite hard work and dedication and the requisite amount of attention being given to the weather. From our point of view, it just seemed that whenever we went right the wind went left and vice versa and when we did get the breeze it was invariably at a super deep angle we could barely sail or at a wind speed that would just not get Challenger moving.

Rolex Middle Sea race
Credit: Damiano Airoldi

To say it was frustrating doesn’t cover it; but even as we got into the lightest of airs we still kept active tuition happening at the wheel and had crew changing through the helming role- trying to learn the black magic of manufacturing apparent wind- a trick only available on boats with Challenger’s near sports boat power to weight ratio.

The crux of the problem came as we drew close to the Sicilian coast and most of the entrants in our division tacked away. We continued East with another large group of boats thinking it was a 50/50 choice. When the time came to tack we made our move with everyone else but very quickly realized that the wind was too light for us to proceed and whatever sail combination we tried boat speed continued to drop until we came to a complete stop and lolled around under slatting sails for the night.  By the time the sun next reached us literally everyone has left us behind.

It is an incredibly hard moment when the penny finally drops and you see clearly that your best efforts and most cherished desires for how things are going to go- come to an abrupt stop.  As a career sailor, this has happened to me before but its been a long time since I was dead last in a race with no hope of catching up and it left a bitter taste. The crew who had joined us for this event handled it well- pointing out that due to our exact circumstances we now had a fantastic view of the Messina Strait and the beautiful landscape surrounding it – Laugh or cry… I guess we decided to laugh.

Rolex Middle Sea Race
Credit: Damiano Airoldi

Rolex Middle Sea Race ‘Plus’ (™ ! )

The conversation soon came up about using the engine and we agreed to ford that stream if and when it became clearly obvious that we would not be able to complete the race route within the allowed time. The final decision, however, was somewhat taken out of our hands when we found ourselves once more adrift a few hours later with the sails hanging lifeless and slack right in the path of a ferry making its way at speed through the Messina Strait. Technically we could have used the engine to maintain safe distance then returned to the position where we engaged the drive and begin to sail again – having made a note in the log to pass to the race committee for their assessment at the end of the race.  As the ferry passed clear away to port, I looked around at the faces on deck and it was clear that everyone was sick of sitting on a boat with no wind racing only its own image and the moon for another night.

So the engine stayed on and once the decision was made and the inaugural edition of the Middle Sea Race ‘Plus’ (™ ! ) kicked off- the mood on board resolved it’s self into something a little less tense and an interesting on-line search for how we could make the voyage ahead of us both interesting and enjoyable.

The rest of the evening was very pleasant and we had the unbelievable opportunity to see the Volcano of Stromboli erupting throughout the night.  I may have sailed all these miles but Wow! watching a volcano erupt at night is something beyond any expectations I had going into the event. One of our crew even managed to recover some pumice from the water… now that’s authentic!

The first thing to get sorted out logistically was the fact that we knew we would have to motor basically the entire East-West axis of Sicily. When we set off on this kind of race- one that rarely departs from coastal passage-making we normally have about 24 hrs of fuel onboard – in fact under ORC racing rules I believe we are often prohibited from having more than that available for this type of race. To this end, we had to have a plan in motion as to how we would continue on into the rest of the event with a safe reserve of fuel. The solution was found when we realized we could go into Cefalu on the Northern coast of Sicily and arrive not only in time to meet the marina manager before he went home (so we could get fuel) but also visit an extraordinary restaurant that promised to give us a window into some of the most delicious and beautifully prepared food local food. It may not have been exactly what we would have chosen: to be motoring all afternoon and sitting in a restaurant in the evening … but once this course of action became our reality we all took the very best from the experience and enjoyed the adventure as a team.

Not so becalmed after all

Leaving Cefalu after a few hours ashore we headed to the new wind in the West and the turn South that we knew would mark a very distinct change in our experience. As any casual observer to the 2019 race will know the first boats around the course had a pretty steady run, however for those coming along behind whether 12 hours or 24 hours later the weather took a turn for the decided worse and that meant by the time we got to the corner 48hrs after the leaders we faced 40 knots of apparent wind and very disturbed seas. A number of waves of the waves had large breaking tops and hollow backs creating massive shock loads and huge impacts for the boat and crew.  I knew we were going to be in for a beating.

To put this in perspective let’s just review my unique point of view. I have raced through the Southern Ocean solo on an Open 60, I have beat upwind for weeks against the North-East Monsoon in the Kurio Shio current South of Japan, I regularly sail the length of the Gulf Stream from the latitude of Miami to Nova Scotia and I have passed through Hurricanes in the North Pacific and Atlantic with wind speeds of over 70kts blowing for days. SO. If I say it was rough. Read my lips. It was rough.

To maintain safety, I drove the entire leg- which sounds odd initially but this was a decision made carefully and with great consideration. I let the mate, Daniel ride out the afternoon and evening inside the boat in full gear ready to go- thereby maintaining his focus and energy should he be required in an emergency. Running us both down on deck working in tough conditions as the leg dragged on would only have meant two tired people trying to solve a problem should it occur instead of one clear-headed person stepping in with full energy and maximum potential to take over if it was necessary. That is a good use of resources and the only downside was I would get a bit tired.  That seemed like a good deal.

The driving was extremely physical and required a lot of concentration not only because of the state of the seas but also because as the night closed in the wave angles and sizes became harder to see until the very last minute whereupon they required radical and dynamic steering inputs to save the boat leaping clear of the waves doing unnecessary damage. It doesn’t really matter what boat you have- if you are sailing over heavy waves sets at 9 kts you need to be doing it for a very particular reason to take that risk with your equipment and crew otherwise the risk/reward equation does not make sense.


By the time we reached Pantelleria and I looked at the possibility of continuing on to the next turning mark at Lampedusa the situation was clear. I was the only person on board able to steer and had been doing so for 14 hours. The weather was not due to lessen any and only half the crew were functional. We had one sprained knee and a few people for whom the intensity of the situation was starting to overcome their adventurous nature. In short, we were moving out of our comfort zone as a crew into what can easily become a potentially emotionally damaging if not physically damaging experience and I was not going to allow that.

Charter race sailing is about having fun and trying your hand at something new. It is more akin to a holiday than anything else – albeit an adventurous and challenging holiday and we don’t need to make ourselves miserable and anxious learning that there is a reason people spend a lifetime in the world of professional sailing to get to the point where they can handle anything. If the stars align and it’s a good weather pattern for the race and everything goes well with the boat and with the crew dynamic I am as keen as the next skipper to push on and try to get the best position possible but in the situation, we were in there was only more misery and many more hours on a bunk sick or on the deck in high winds and crashing waves ahead- and for what? To say you completed the course.  Please.

So, into Pantelleria we went- our second stop on the 2019 Middle Sea Race + (™) and boy was I glad I had kept Daniel the mate on ice until that point. Whilst I was physically fine form my long trick at the wheel my awareness and processing of the layout of the harbour, the rocks, the channel marks the wind patterns, etc felt sluggish and imprecise and I was glad to hand over operational control of the deck, the mainsail drop and jib furl, fender and line set up and pilotage to him. I drove the boat and did what I was told and took the advice offered and though this professional teamwork and understanding we had no problems, the situation as quiet and good mannered and the boat docked safely and securely without fuss in a high cross wind in a limited space.

In the morning, we had the rare opportunity to see Pantellaria which I understand is a culinary destination for many in the region- I believe the island is well known for its recipes including capers and seafood. We took the day on the island allowing the crew to get some proper sleep and we had a superb meal at which I consumed the largest T-bone steak I have ever seen. I am surprised I could afford it let alone consume it!

An early start the next day with a forecasted North Easterly led us to the last leg of our circuit- a straight run back to Malta.  The crew had the opportunity to fly out of Pantelleria but everyone decided they would like to finish what we started together- it was after all our adventure- not quite what the brochure described, but unique, created from our own decisions and agreed upon by everyone. Unfortunately, the wind was not as strong as predicted and we had to motor pretty much the entire way but stories were swapped, stars gazed at one more time, a good curry enjoyed and the lights of Malta eagerly welcomed and watched as they grew larger and larger and finally resolved themselves in the finish line under the walls of Valetta.

Renewed respect

What I take away from this voyage is what I always get from sailing- new friends, new perspective on life, new memories like the sight of Stromboli spewing fire into the night. I have renewed respect for the ocean and the challenges it can send- both in its stillness and in its storms and finally I have an opportunity to try to understand why do I go to sea- I often quote the phrase ‘he that would go to sea; would go to hell for a past time’. It’s not set, it’s not on a schedule, it’s not certain and Triumph & Disaster can visit you with impunity at any time, so why go? Because behind the illusion of control that’s exactly how life is and yet we forget that behind a veil of forecasts, timetables, contingency funds and get-out clauses.

I think I still enjoy going to sea even after twenty years, even to end up DNF because the sea is the only remaining frontier where anything can happen- and normally does.


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