Even if you’re caught up by unpredicted gale winds, if you know what you’re doing and have a well prepared boat, you’re fine.
Keep Calm and Carry on
Most of times the weather is quite predictable… for a couple of days that is. Still, it sometimes turns out (very) different.
Also, it makes a difference where you are. 20 kts should be quite okay normally, but on a lee shore or against the tide it can become a bumpy ride…
Then it all comes down to keep calm and carry on.
If you’re looking for someone experienced to accompany you, I could help you out.
When you think about reefing, put in a reef. As a rule of thumb, that’s what I do. The thoughts that comes into my mind pop up for a reason: experience
Learn how to read weather forecasts. Local forecasts are only valid for about 24 hrs max and even then. Looking at the sky and knowledge of reading clouds can be helpful .
For the bigger picture you literally have to look at the bigger picture e.g. by downloading gribfiles from XyGrib, showing the development of pressure systems.
When the swell isn’t coming from the obvious direction, be prepared for a wind shift and strong winds.
Keep in mind that in 40kts, you’re better off on the big but long waves of the ocean then in the shallow North Sea or Bay of Biscay.
Ending up in bad weather is inevitable. The thing is however, that what you experience as bad the first time, the second or third time doesn’t seem to be as bad; more like bad-ish.
Experience is the magic word. As long as you’re prepared, as long as you keep your boat well prepared, you should be okay. Key is to also prepare your crew, share your plans, give them the opportunity to ask all their questions and address their concerns. Let them know that when you’re shouting, it’s not because you’re panicking or because you’re angry. It’s because they might not be able to understand you hear you otherwise. Strong winds make strong noise.
You might also want to reassess your passage plan. If there is plenty of sea room, you have the option to change course or, when that happened to me, leave Madeira as destination for what it is and sail down to the Canaries.