Vacation Destination

Question

So, a while ago I asked a friend to plan our next vacation. I had to tear him away from his computer and this site to get him to do anything. Which was probably my first mistake. I don't know if he is trying to get even or is actually excited about this vacation.

Anyway, he emailed me this list and said see you there. I have no idea what any of this means, so I went to talk with him (he was only in the other room) but all he kept mumbling about was ordered lists and strings inside of strings. I don't know if its important or if he finally cracked.

4) Waiter
7) End
9) Pause
3) VMD title
5) Fast feathered swimmer
2) Wait in line
8) Ancient
6) Transformation process
1) No pattern

7) Instructions
6) Long lived
3) Aromatic leaf
1) Blue box
2) An arrangement
4) Binary single character
8) Contains pictures
5) Small bite

4) Information
2) Non-standard layout
6) Home Sweet Home
1) Nothing
3) Magical root
5) Multipurpose tool

3) Exterminate
8) Set aside
5) Pile up
2) Coffee
6) Unknown
7) Rules
1) A hat
4) A friend and an enemy

Once you're finished with the list don't forget to cross your I's and dot your T's

What city does he have in mind for our vacation?

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My friend is a programmer by trade, but he eat, sleeps, and dreams code anyway. He also likes British science fiction.

Answer 1

No answer yet but perhaps a way to proceed...

It seems like each phrase can be represented as a different word - blue box, for example, is tardis. Tardis has both a t and an i in it so I feel like that's on the right track. I suspect after finding all of the words, you would replace the i's by dashes ones and the t's by dots zeros, place each list in numerical order and then decipher the morse code binary.

Answer 2

NEW ATTEMPT

I'm guessing that the answer to each clue must contain

the letter I and the letter T.

So some attempts at the clues are below.

SET 1

4) Waiter = hesitater (loiterer or maitre d')
7) End = terminate
9) Pause = interrupt? (or intermission or interlude?)
3) VMD title = veterinarian
5) Fast feathered swimmer = gentoo penguin
2) Wait in line = loiter
8) Ancient = prehistoric (or primitive)
6) Transformation process = mutation
1) No pattern = arbitrary (or erratic)

Perhaps instead of using the clue numbers to reorder the clue's answers, we instead use those numbers to

take the corresponding letter from each correct answer.

So if a clue is numbered 4, take the 4th letter. Unfortunately, at the moment for the first set above that gives me: [I/T] A [T/S/E] T O O? [O/V] I [A/E]

I can't really make sense of that, so maybe that use of the numbering isn't correct.

SET 2

7) Instructions = directions
6) Long lived = ancient?
3) Aromatic leaf = cilantro?
1) Blue box = Tardis
2) An arrangement = ?
4) Binary single character = bit
8) Contains pictures = illustrated
5) Small bite = appetizer?

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OLD ATTEMPT VERIFIED WRONG

Based on Morgan G's idea, I took a crack at the first set. Nothing definitive, but perhaps if you squint you can see

New York?

Because if you

Reorder them by their number, then figure out a word for each, then take every letter i in the answer to be a morse code dash and every t to be a dot...

1) No pattern = arbitrary → -. → N
2) Wait in line = stand → . → E
3) VMD title = veterinarian → .-- → W
4) Waiter (server?)
5) Fast feathered swimmer (gentoo) penguin .- or - = A or T??
6) Transformation process (mutation would yield U...)
7) End = terminate → .-. → R
8) Ancient = prehistoric → -.- → K
9) Pause (break?)

The trouble is that

if this is the correct approach, there are many possible answers to almost every clue, and thus it's hard to definitively answer this.