Not sure about trippy, but Skyrim blew me away when I first started playing it. I actually got a little dizzy while climbing up mountain paths, very well done (on the scenery, anyway. Still don't quite understand why all the women move like linebackers.)

WIP3OUT

I'm with you there... I love the scenery where you fight the T-Rex in the first game. I still think it looks awesome.

Morrowind with Overhaul Mod at max.

Looking at the sunset or sunrise with the water reflecting off it was an amazing site.

Oh and the 3 Uncharted games and Last of Us

Grand Theft Auto 5 I am surprised the Graphics looked that stunning despite the incredibly large world, I think its all in the lighting

Battlefield 4 trumps 3 visually

Crysis of course.

And Arma 3 has the best lighting of all games combined. Night is increadibly dark as it should.

It's kind of a bug. There is some mod that fixes this - most women will walk in more female way after that - just warrior women will still have that heavy masculine stroll.

Baten Kaitos. Both odd and gorgeous.

I want to retract my earlier post.

THIS is what I call 'visually mesmerizing'! YEAH!

Final Fantasy VIII, back in the Playstation days.. Absolute fan. Dreamcast Soul Calibur and Shenmue, too. Ps2/3 Shadow of the Colossus.

Haha...you have described my fish out of water situation when I ventured out on my own for the first time to a foreign land quite accurately besides the shit part. Also apart from the new Glidos program I am sure what made the game really visually arresting for you was all those nude patches for the Tomb Raider games, as I am pretty sure that Lara's two biggest pixelated weapons kept you mesmerized. ;)

Ok before this thread devolves into further perversion let me mention my picks for games that I have recently found to be visually unique with a trippy aesthetic for authentic reasons.

Broken Age - The entire art in the game is inspired by the quirky and offbeat stylings of Nathan Stapley aka Bagel. The game is like a set of his wacky paintings.

Jazzpunk - I don't really know how to describe it any other way than calling it unusual and trippy as well. Check out the trailer.

Child of Light - This game has one of the absolutely most beautiful and gorgeous art style that I have seen so far this year in a game, it is literally like a storybook fairytale come to life as can be seen in the trailer.

Shelter.

GOOD ONE.
Just started playing it.

Morrowind, in the sense that I ended up sightseeing more than playing. I was really in awe of the skies, the waters, the weather, and the general landscapes. I loved my virtual stay in Vvardenfell.

Maybe other games have increased the eye candy since, but Morrowind's pacing, design and novelty played a big role. To a much lesser extent, Far Cry was also quite betwitching, especially with its freedom to dive into clear blue water from lush bright green cliffs.

Apart from that, Symphony is quite mesmerising too, especially as your selected music could contribute to the transe. I often find myself "dancing" with the enemies more than maximising my fire power (without realising it, I end up moving and fire in tempo, which is a disadvantadge).

Some management and strategy games of all sorts can end up mesmerizing you with their little AI characters going through their acrtivities. Tropico, Evil Genius, etc. Basicaly, all games that has you set up a system and watch it function can do this. Even some tower defenses.

And then, there's these madmen from Amanita Design. Seriously...

Oooh, you wanted games with trippy aesthetics. I thought "Trippy One" was some game, lol.

Well, here are some games with a loose definition of "trippy" aesthetics: FRACT OSC, Bad Hotel, Another World, 3079 and 3089 action RPG games, and Botanicula.

It's an interesting question, though. Not a lot of games with that LSD trip look. that I can think of.

I really do love the vistas of outer space in (here I go again) I-War 2.

First time I played FarCry was a mesmerizing moment, as well.