Ask HN: 2 weeks off work, what to do?

Travel. Dont over think it. Go now, go light. Just book a hotel\hostel somewhere out of the beaten path for a few days to get your bearings then explore and wing it. You dont need\want an itenary, doors will open to you unkown when you take the first steps there. Visiting natural wonders is a good way to guide you..

Personally two things come to mind: Hedonistic or Noble

Hedonistic: Fly to Amsterdam one way, buy a few doses of truffles, smoke some weed, see some boobs or whatever floats your boat I dunno. Then go to centraal station, buy the first train ticket and keep traveling. Stay in hostels, be open to meeting people. Every hostel will point you to walking tours in the morning, and usually a group will go together. Just join that group.

Saying "Hey, I've got some mushrooms, why don't we all go find somewhere to do them and hike" is actually a great icebreaker at a hostel. It's how I met my (sober) wife. Making friends at hostels throughout Europe was how I rebuilt my life after burning out on my 100% tech social network.

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Nobel: Call up Habitat for Humanity, tell them you have 2 weeks free and want to help out on a build if they have any open in the country. I did this as well, it's how I learned carpentry.

Be wary, some ppl in bars abuse of you when you go the Hedonistic type. They think you're gullible and drunk (so don't be too drunk)

Last time I did that (not in Amsterdam), a group of 5~6 sailors wanted to come in my hotel room. (And they also wanted me to pay for the note at the bar and for the taxi) (these were memorable holiday, for the record)

@op Don't you have internet friends that you could join in some other country ? Or is there some city that organises a mildly interesting fair around, with boonies to explore around ?

Go to the gym, read great books, meet new people.