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Actually (oh dear) I was on one of those weekend city breaks with the missus (at her insistence) - I never really got pissed once and certainly no prostitutes. I just found the cheap, strong, lager a nice way to anesthetize myself against exactly how much money I'd parted ways with in order to spend a weekend in an utterly mediocre and tiresome city.
Now, I'm not particularly au-fait with other ex-communist-shithole eastern European tourist destinations (Budapest, Riga, Krakow, etc) to make a direct comparison - and for good reason: I wasn't there for the fanny or the banter or to get pissed - I just got dragged there by the missus who, apparently like you, got sold on the idea of Prague being some kind magical city of culture when really it ranks somewhere between Chester on a good day and "Amsterdam with a mildly interesting clock" on a bad one.
Admittedly the Old Town was quite nice but packed like a sardine tin with bovine tourists and the kind of low-end fixed-price three course menu restaurants you find in the shit ends of Brussels and Paris and shops selling Trdelnik for an insane markup in much the same way the chancers in Montmartre try to sell you a Nutella filled crepe for 10 sodding euros.
> Once you get outside the couple of very touristy main streets, there's loads of great pubs and places offering local food.
I did find some nice bars and restaurants and even had some passable food (as in it passed for food, sort of) and I agree that the tram system was fairly straight forward. One thing I found impossible, though, was buying a damn tram ticket and so I found myself traipsing up and down for free because I figured paying whatever Monopoly Money fine was probably easier than trying to figure out the Babbage-era Difference-Engine that apparently passed muster for a ticket machine.
> I feel you, like myself were probably mesmerized by such cultural wonders as the astronomical clock
The astronomical clock was OK, we sat around and waited for it to chime the hour along with around two million other idiot tourists. The panthéon and the museum of arts et métiers in Paris were both far more interesting and cultural as was practically any building I visited in Rome. Or, well, anywhere I've been really. Have you ever really paid attention to the carvings around the doors at the Notre-Dame de Paris? Now that's cultural (if you're educated enough to know what you're looking at).
The castle was likewise OK, although again nothing special compared to other, better, castles I've visited. I did get to fire a crossbow for 10 kroner though, got a bullseye and allowed myself to prattle on about projectile arcs and dynamics for a good half an hour afterwards. Possibly the most fun I had on the entire trip. The gallery of replica armour was a nice touch, a sort of mini-Epcot for people who think they know about history ("look honey, a real set of Japanese Samurai armour!") and a lovely way to get prepared for the disappointment of the replica "medieval" statues on the Charles Bridge.
Despite my general lack of experience in visiting post-communist shitholes I definitely had more fun in Kiev, although possibly with extenuating circumstances.
> where as I get the impression our esteemed college was most likely more concerned with how pissed he could get
Honestly, you make it sound like I was in Hull or something.