My question should be similar to this one : http://anarchy101.org/6584/what-good-anarchist-holidays-what-purpose-holiday-your-life
But it's different. I wondered what you think about making holidays/vacations and trips in an anarchist way.
I think that, as an introduction, you shall never consider what you are doing as "tourism" and behave like a tourist. Like not taking part to things, get served, soil everything by the simple fact of being there, etc.
I give you my answer in the same time.
So basically, all conventional holidays were generally total disaster for me as I really hate "normal" and conventional things in general, but especially the pre-conveived, artificial and "ready to consume" aspects of entertainement, recreational activities and the tourism and leisure industries.
That really makes me sick most of the time. Even I also like the sun, drinking margaritas, making veggie BBQ (lol) and this kind of cliché things. As paradoxal as it may seem.
So my best "holidays" memories are about trips and/or events that weren't really prepared or conventional.
I won't give precise examples here of what I did.
But I can recomand you : DIY music festivals, or anarchist summer or winter camps (;-)), or making wilderness camping with friends (very good for getting a bit out of "civilization"). Making hitchiking, going in squats in others cities (taking contact with people before). Meet new people, friends, comrads, etc. Some of things that have been sometimes critized as "anarcho-tourism" by some compas.
But I never saw it that way and always tried to take part to the life of places where I've been and joining activities or even struggle with people where I were. And things always worked well.
Something that some people do here in Europe and that work pretty well (especially if you are not from the country where you do it) is to defraud the train on long distance or jump and hide in "commodity trains" (like "hobos" used to do). For what I know, controllers, when you meet them, barely never call the cops. And even if they do it, you don't risk much in much countries of western europe. Just take some advice and tips from people in the country where you are before you do it.
In last resort, especially when you live in squats or collective housing or flat sharing and you don't have much money, is to "invite holidays at home". The principle is simple : you let people know, in "anarchist circles" or friends from other cities or countries that you can host one or several people for some days or during an event. You often have good surprises.
But you need to work on your "anti-social" tendencies. Which is not always easy. As you also may have bad surprises. ;-) But it's no big deal to me.