I am a C++ developer, slowly getting into web development. I like LISP a lot but don't like AllegroCL and web-frameworks available for LISP. I am looking for more freedom and ability to do cool hacks on language level. I don't consider tabs as a crime against nature.
Which one is closer to LISP: Python or Ruby? 
I can't seem to be able to choose from Python and Ruby: they seem very similar but apparently Ruby is more functional and object-oriented, which are good things, while Python is more like Perl: a simple scripting language. Do I have the right impression?
PS - This might seem like a flame bait but it's not really, I'm just trying not to go crazy from OCD about switching from RoR to Python/Django and back.
Speaking as a "Rubyist", I'd agree with Kiv. The two languages both grant a nice amount of leeway when it comes to programming paradigms, but are also have benefits/shortcomings. I think that the compromises you make either way are a lot about your own programming style and taste.
Personally, I think Ruby can read more like pseudo-code than Python. First, Python has active whitespace, which while elegant in the eyes of many, doesn't tend to enter the equation when writing pseudo-code. Also, Ruby's syntax is quite flexible. That flexibility causes a lot of quirks that can confuse, but also allows code that's quite expressive and pretty to look at.
Finally, I'd really say that Ruby feels more Perl-ish to me. That's partly because I'm far more comfortable with it, so I can hack out scripts rather quickly. A lot of Ruby's syntax was borrowed from Perl though, and I haven't seen much Python code that feels similar (though again, I have little experience with Python).
Depending on the approach to web programming you'd like to take, I think that the types of web frameworks available in each language could perhaps be a factor in deciding as well. I'd say try them both. You can get a working knowledge of each of them in an afternoon, and while you won't be writing awesome Ruby or Python, you can probably establish a feel for each, and decide which you like more.
Update: I think your question should actually be two separate discussions: one with Ruby, one with Python. The comparisons are less important because you start debating the merits of the differences, as opposed to which language will work better for you. If you have questions about Ruby, I'd be more than happy to answer as best I can.
Please advise on Ruby vs Python, for someone who likes LISP a lot