Don’t they both convey the idea of “intending to do something”?
Take the following example:
今度の休みに何をするつもりですか。
今度の休みに何をしようと思っていますか。
Do they both mean: “What do you intend to do next holiday?”
Is there any difference in nuance?
I asked my tutor this exact question, and she said つもり has a nuance of being more concerned or worried - but from what I can tell they are incredibly similar.
As a side note, an interesting discussion took place here:
And two natives seemed to offer opposing opinions on which has a stronger feeling of determination. Finally someone explained that while つもり comes from 積み重ねる, and essentially means piling in ones mind - the language is evolving, and they disagreed that there is a definitive answer on which is stronger in intent.
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I see, so they are very similar. Thank you very much! Oh and welcome to the forums! 
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personally always felt “するつもり” to be far more direct in expressing your intention/asking for an intention than “しようと思っていますか” - of course just my gut feeling when reading stuff, but the first one sounds more like you really want the other person to clarify what they are doing next holiday (as per your example), maybe even sounds a bit like interrogating more than asking depending on the context?
Meanwhile しようと思っていますか sounds a lot more polite to me simply due to how the construction works (look at the verb-form and the link to the “I think I am gonna…”). It seems a) more polite, aka what I would use if I asked this someone I am not super close with and b) sounds less certain about the other person having “planned” something for next holiday and more asking “if and if so what they have planned”.
Now take this with a grain of salt and I could be wrong, but I always kinda took the “しようと思っていますか” to be the more polite and less direct approach/ less of an undertone/assumption-nuance…? If that makes sense. Also seeing how natives arent really sure either on the differences and what sounds more forceful, sorry in case my language feel is completely off here, most of it is from immersion-reading without ability to really 100% control if I interpreted things right
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It does definitely make sense, as in japanese indirectness is usually more polite. I can see how this could be the case. Thank you for your view.
We were taught these express different levels of conviction. i.e. expressing something via ～ようって思ってる would be expressing that you are considering doing something, while ～つもり would be expressing that you have decided to do something.
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