@Geekflyer. I sympathise, I have been there. For me there are two sources:
1) (And you would probably have to do this anyhow if using a club aircraft), you do a foreign checkout with an instructor and he/she will help you with FLP, GAR forms, the lingo (unlike other flights you have to ask ATC to activate your flight plan and remember your time of departure and ETA for a country zone boundary (normally mid-channel if going to France)). Then you do it a 2nd time on your own, and then you expand on it. Things like SkyDemon and other such tools help remove a lot of the paperwork side of it out of the equation.
2) The kind people on here will no doubt help you if you outline a plan and highlight the gaps. Last year I flew to La Rochelle, and while I had been to France and Channel Islands numerous times, it was my first time going to a place not on the usual UK CAA chart :-) Some kind people on here gave me advice about the 2 different charts I might want, danger areas to avoid and so on… Of course, you would expect local instructors or other PPL’s at your airfield to also help too….
Interesting points made.
I don’t think you can do an international solo flight before you have the PPL, because you need an ICAO license to cross country borders. And you don’t have one at that point. Any country doing that must have done a deal with the other one.
I think the training establishment has a lot to answer for here. They could teach pilots to have more capability on the planning front. But I don’t think they want to do anything which increases the cost of a PPL, or even complicates their life too much. When I did my VFR to Europe presentation in 2012 it was very obvious that none of the several schools (where I wanted to leave a poster) would support it.
During my training, some very worthwhile foreign fly-outs were made but all were rigged so there would be an instructor in the RHS on every leg, so he could take over and fly the aircraft back to base if the wx got bad. Of course that also maximises the revenue because every leg generates both rental and instructor time.
EVERY pilot really felt a bit insecure before flying abroad the first time
Yes of course. Everybody feels nervous and insecure when doing something for the first time. The difference with flying abroad is that is not a requirement for the test – except in the interesting Maltese example! – so little if anything is said about it in training. Over the process of learning and taking tests, we do new things all the time, but each time after due preparation. That is why Peter’s initiative was so nice. it really fills a gap.
As for the French never flying abroad: their traditions are indeed very autocentric. But I think the Spanish are no better, one VERY rarely sees EC-registered GA planes.
The situation is, unfortunately, even worse among microlighters: flying slower, they have to spend more time to get abroad. Also, they are not flying in a legal continuum: microlights are regulated nationally, and rules can differ a lot. The strongest example is Croatia, whose microlight ruling evaporated when they joined EU, and now there is a vacuum. Another strong example is Italy with its differentiation between “basico” and “avanzato” microlights: not a bad idea, an sich, but it takes some getting used to.
There is a German microlight forum I frequent, and from reading there I reckon that 99% of forumites have never flown outside Germany. Some clubs seem to organise group trips abroad, though – as is done in my own Belgium, though sparingly, and little advertised.
It would surely help if someone organised a group trip, perhaps for the weekend, from somewhere in the UK to somewhere on the continent, aiming for PPL’ers with perhaps a 100 hours solo in one or two years, and looking to expand their horizons.
What’s even more shocking — 99.9% of the US PPLs have never flown abroad!
Shocking? Not a surprise to me! But, surely, much more than the French the US’ans have everything available at home. That said, their traditions and culture are at least as autocentric.
I’ve found most people the world over prefer not to deal with bureaucracy and corruption. Those who have the opportunity to carry on their lives that way, generally make that choice. That said, I know people in the US who fly their own planes to Mexico once a month or so to provide medical and dental care to the locals for free. The good news for them is that the number of homicides in Mexico has started decreasing from the 2011 peak of 27,000/year.
I’ve been to more European countries and more areas within those countries than most Europeans. 
I hope to fly abroad some day – but do find the idea slightly daunting. Bureaucracy and corruption is a concern – some people clearly find it easier to deal with than I do but I’d be quite jumpy about flying e.g. to North Africa, Eastern Europe. Then the thought of violating some rule – flying over an unmarked French nuclear power station etc. or landing a C152 on a 500M Belgian runway and potentially getting somebody else’s aircraft impounded doesn’t appeal.
Added to which a lot of rental aircraft are getting older and the thought of getting one stuck abroad doesn’t appeal, or having to get back to work and having to leave it there due to weather… I can think of quite feasible scenarios where I might get myself into real financial difficulties should things go wrong. I’d be very happy to be persuaded otherwise but suspect that I’ll not fly abroad until I own my own aircraft where having to leave it parked for a few weeks wouldn’t be such an issue and if you do screw up you’re the only person involved in dealing with the consequences.
You are very unlikely to come across corruption in Europe. Not directly anyway.
And outside Europe (by that I mean flying to or via Africa, Russia or the Middle East) it hasn’t been easy for decades, as far as I can tell. Today, 100LL availability is the biggest practical issue, and there is a load of other stuff like overflight/landing permits. I once planned a trip to Luxor and it was just a load of hassle.
The poor security situation in much of the world doesn’t help. Afghanistan is supposed to be absolutely stunning but would you fly there right now?
In flying one needs to keep the reward to hassle ratio as good as possible. Different people like to do different things (e.g. some like aerobatics) but being able to organise things to deliver a good reward to hassle ratio is absolutely fundamental to staying in the game long-term. I’ve been flying post-PPL for 12 years and enjoy it as I have ever done before. Of the 90%+ of new PPLs who give up in the first year or two, most never got much out of it.
The only things that get harder are the trip writeups because it’s hard to do one with significantly new stuff I hope to do some trips into Sweden and Poland this year.
Perhaps the best single thing to optimise the reward to hassle ratio is to get out of the school environment and buy into a syndicate.
I know many pilots who are not flying further than 50 miles to the surrounding airfields.
(Unlikely to come across corruption Europe? You mean in aviation, or in general?)
It is common that pilots even fly their Binanza, Mooney, TB or Cirrus around the field and never go abroad. I don’t care one bit! I asked a guy with a Turbo Arrow one day why he never flies away, like to France. Answer: “I don’t like the French”.
