Most challenging passage?

Narrowing it down to just one is tricky but the three that spring to mind for different reasons are
Crossing Biscay N Wales to N Spain because it was my first long singlehanded passage
Jamaica to Panama - because of the weather
Galapogus to Marquesses - 34 days on your own feels quite a long while
 
I once rounded Cape Calshot on a warm weekend in August. Never again.
I feel your pain :)

Seriously, though, between the once a year charterers and the weekend racers - not the serious ones, who just want you to be predictable, but the ones who take themselves seriously and expect "I'm racing" to trump Starboard tack, it can be challenging.
 
Years ago now…….the traditional getting back to work on Monday bad decision making……..left Cowes with my father in his ne Halcyon 27 to get to Chichester,running before a force 5 and building sea………we made it to the bar but had to lash ourselves in as the boat tumbled through the maelstrom…….once in the harbour the relief was palpable!
 
I have been in numerous situations where I wonder what I am doing out there. But seriously, the hard bit is getting the nerve to leave port, when the wind whistles through the rigging & the water looks white outside. Then in a big rolling sea getting ready to enter port can be a bum squeak moment. Especially if it is a new one & I am seasick and exhausted because of it.
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Perhaps Ostend to Burnham & hove too in my Stella in the 70s for 4.5 hours off the Falls in a 30 hour trip & F9 for part, is the one I remember the most. The first time a wave broke over the bow & water filled the open cockpit I screamed in fear. But I soon realised that it was not the broken wave that was the worse. It is the one about to break that has the force in it. White foam is just that. With an open cockpit I was pumping every 20 minutes.
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Arriving in Ostend with vomit on the side deck is not unusual. Virtually all my sailing has been SH, so seasickness & handling it has been an issue.
But in the end one just looks at them as another trip & par for the course. None really stand out. It is all part of sailing & mostly I have never been really frightened, because I have always known that my boat is well looked after & well able to look after me. I just have to use my skills & common sense & stay calm & always build a new plan in my mind as required.
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I record all trips in the log. so it is fun to reminisce from time to time.
 
I have been in numerous situations where I wonder what I am doing out there. But seriously, the hard bit is getting the nerve to leave port, when the wind whistles through the rigging & the water looks white outside. Then in a big rolling sea getting ready to enter port can be a bum squeak moment. Especially if it is a new one & I am seasick and exhausted because of it.
.
Perhaps Ostend to Burnham & hove too in my Stella in the 70s for 4.5 hours off the Falls in a 30 hour trip & F9 for part, is the one I remember the most. The first time a wave broke over the bow & water filled the open cockpit I screamed in fear. But I soon realised that it was not the broken wave that was the worse. It is the one about to break that has the force in it. White foam is just that. With an open cockpit I was pumping every 20 minutes.
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Arriving in Ostend with vomit on the side deck is not unusual. Virtually all my sailing has been SH, so seasickness & handling it has been an issue.
But in the end one just looks at them as another trip & par for the course. None really stand out. It is all part of sailing & mostly I have never been really frightened, because I have always known that my boat is well looked after & well able to look after me. I just have to use my skills & common sense & stay calm & always build a new plan in my mind as required.
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I record all trips in the log. so it is fun to reminisce from time to time.
I 100% agree that it's the leaving and arriving that can be most challenging. Then the first time of everything else is testing as it's a new experience. It doesn't get easier but you know what to expect.
First time in a gale- I was terrified
First time having to sail onto a pontoon due to prop wrap - very nervous
First time running out of fags with 3 days left to sail - slowly lost my mind!
 
I once rounded Cape Calshot on a warm weekend in August. Never again.
😎
I once came down the Solent in foggy sort of mizzle drizzle sailing.

Since I now had a boat with something called radar and something expensive that I had bought called ChartPlotter, I thought well why not?
So I turned them both on.
Calshot was no longer a shot in the dark. Which was nice.
 
😎
I once came down the Solent in foggy sort of mizzle drizzle sailing.

Since I now had a boat with something called radar and something expensive that I had bought called ChartPlotter, I thought well why not?
So I turned them both on.
Calshot was no longer a shot in the dark. Which was nice.
I had you down as a sextant and lead line man😂
I initially misread that as "you made it to the bar and went on the lash" and thought "Sounds like normal conditions for the South Coast?"...
😂😂
 
The good news is that my worst memory is 40 years ago. I credit that to the learning curve and much improved weather forecasts and communication.
Leaving Brighton in a F7 westerly that was forecast to decrease, the plan was to aim for Boulogne because the skipper had to get back to Belgium to pick up his next group of charterers. The wind did not decrease but increase to what must have been F9 with building and reagularly breaking waves. Crossing towards Boulogne was soon ruled out, running before wind and waves was the only option. Entering Folkestone was not inviting, neither was Dover, so we kept on running, with the skipper at the helm and one crew in the cockpit looking out over the stern, the rest of us inside with varying degrees of seasickness. We finally managed to get into shelter around South Foreland and found refuge in Ramsgate. As I was a novice at the time, and not too confident of what the boat and crew could stand, it was a pretty terrifying experience.
Lessons learned: a Rival 32 is a good boat for these conditions, you gradually get used to the circumstances once you realize the boat is not overwhelmed and most importantly: never sail into bad weather under time pressure.
 
Summer 1979, left Herm bound for Swanage with a SW 5-6 forecast, myself and 10 year old sister on board Dad’s bilge keel Sanre 27. By midnight we’d reduced to storm jib only, running at 9 knots, then handed the storm jib, started towing warps and aimed up the centre of the channel, not wanting to get anywhere near the shore. In the morning the wind started to reduce, set storm jib and heavily reefed main and reached into Swanage bay, meeting the life boat out rescuing distressed boats.
Beached the boat, because we couldn’t get on the mooring and then started to be told about the Fasnet race tragedy unfolding. My Dad was in the coastguard, they had gusts of over 100 knots that night.
The boat was fine, running under bare poles with warps out we were doing about 6 knots and quite controllable, if not comfortable. I remember being much too busy to be frightened.
 
In terms of delivery trips, this one was quite challenging!

That is a great story. Interesting to see a challenging voyage where the garden furniture stays on deck!

What is the song at the end of the video starts "There was a man whose love was the ocean...". I would like to learn it!

Edit: Got it, "Fisherman" by Marina Florance.
 
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It's the best stress relief a person can get when you are out on the ocean disconnected from the modern word and slowly becoming attuned to nature. It's so therapeutic for me that I can't wait for my first proper sail of the year.
 
I can no longer make long passages but I can remember spending most of the winter in a state of rank agitation about the prospect of exposing myself to the risks of crossing the southern North Sea. This would worsen in the weeks before the trip, until, out of sight of land, I would discover that this was well within the ability of the boat, and even me, and that for some reason I was having the time of my life.
 
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