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I did a Google search and I found both instances:

... on my mount and instance que pops, I get into instance, finish it, and after leaving instance Im back on my mount wherever I was heading to.

Different strokes though -- I'd much rather have those extra 2-3 days in Turkey or wherever I was heading.

What's the difference between the two?

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In answer to your question, it depends on whether is is the subject or object of the sentence.

The first sentence you give as an example has terrible grammar, so I am going to ignore it and demonstrate proper usage of a sentence ending in "heading to"

I have a speech to give at the theater, so that's where I'm heading to.

This uses preposition stranding, and could be rephrased as

I'm heading to the theater because I have a speech to give there.

Note that "I'm heading" is the subject and verb of the sentence, and "to" is the preposition which joins the object of the sentence "theater".

In your second example "Turkey or wherever I was heading" is the object of the sentence. "Turkey" and "wherever I was heading" are two separate nouns, together which are the places that the subject "I" would rather have extra days.

See also:

https://en.wikipedia.org/wiki/Subject-verb-object

What is the difference between "heading to" and "heading for"?

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  • Thanks! I'm still confused, though. How about this sentence: "I was going to miss his jokes wherever I was heading (to)."?
    – janoChen
    May 14, 2015 at 14:58
  • That sentence seems weird to me. I don't know if it is proper to put the first part of the sentence in the past tense if the second part has nothing to do with time. For example I might say "I was going to miss his jokes when I got to wherever I was heading". I guess in general I talk about missing jokes at a time, not a place.
    – regdoug
    May 14, 2015 at 15:19
  • Oh you're right. So with the when, the right choice would be heading?
    – janoChen
    May 14, 2015 at 15:45
  • Actually, you can see that in my earlier comment there is a "to" after "I got". If you want, you can move that "to" to the end of the sentence to obtain "I was going to miss his jokes when I got wherever I was heading to" which is also valid. In the end, prepositions make fools of us all.
    – regdoug
    May 14, 2015 at 15:50

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