Hi Daria,
Thanks for sharing. I would venture to say that many, maybe most, long distance cruisers would fail some of the items you specified. I know I would.
Now, much of the concerns expressed by Portugal’s maritime officials are good judgment and good guidelines. Do you know whether the rules and the rule enforcement are in response to some incident: say a boat trying to use out-of-date flares and failing or: out of date extinguishers when there was a fire, or pulling using the right-of-way rights of a vessel under sail when motoring and not having a cone showing? Or variations such as these? Or is this some bureaucrat wading in with his/her judgment?
I ask as for (at least) two-pronged reasoning. One is that I would wish us to oppose (most) any requirements that impose a bureaucratic judgment as to best seamanship practices that interfere with the skipper using his/her best judgement as to seamanship. I would, concomitantly, wish us, as club members (and in our other venues) to use our experience to promote voluntary best practices and to challenge (gently) those of us who are making poor choices on the water. If we do not do so, others may step in to do such things as: demand a “license” for us the do an Atlantic crossing, but only after jumping through hoops of various degrees of relevance.
An example for the latter above is when the SAR people get fed up being called out to rescue (and put their lives in danger, not to mention the expense) those who get into trouble, not because of bad luck, but because of poor judgment and preparedness. I believe skippers such as this are fairly easy to document. In these days where setting off an EPIRB calls for help so easily, I believe a skipper who chooses to carry one is absolutely obligated to ensure that his/her skills and experience are up to the challenge (and all that might be expected to go pear shaped in a passage) and that the vessel is similarly prepared for the extremes it might meet. I suspect that we have all heard someone talk about their intentions and shook our heads in quiet concern.
An example of where I would wish my judgment to prevail over some bureaucrats. I keep my flares (and I buy high quality) in a perfectly waterproof protected container that is still easily accessible. In the US there are flare requirements (age, type and quantity): insufficient in my estimation for a wide-ranging vessel. So, I keep my out-of-date flares for a few extra years as back up to my up-to-date flares that meet the requirements. I am confident that my “old” flares are still good. I have set off flares that were 8-10 years of age (years out-of-date) and they worked perfectly as did many flares of various ages and manufacturers (coincidentally, this was in Lagos, Portugal, when I set up a flares demo/practice session and a fire extinguisher demo/practice session when I wintered over there in 2006). (One suggestion coming out of this session, was to have some work type gloves in the flare bag.)
My best, Dick Stevenson, s/v Alchemy

Portugal has begun fining cruisers who upon vessel inspection are discovered to have expired flares, fire extinguishers and life rafts. If you don't have an item that is not required such as a liferaft, you're fine. But if have a liferaft even though it is not required, and it is out of date, you can be fined. Also, they are intensively policing adherence to COLREGS (black ball, white light when anchored, cone underway when sails up and motoring, etc) There is a useful discussion here: http://liveinfo.lagosnavigators.net/httpdocs/bureaucracy/application-to-visiting-yachtsmen/

Vice Commodore, OCC