That’s one of my leeches because I always think sailboat. I really do think that word is a bug. The kanji importing people back in the day got that one wrong.
A recent favorite is 宇宙人
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I’ve for a long time liked the following:
幸せ （しあわせ） To me, it sounds like what it means.
行方不明 （ゆくえふめい）No idea why, haha. I just like the sound.
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Words with 不明 are always fun to me – 消化不明 (しょうかふめい) is a favorite because the phrasing of “uncertain digestion” is a lot more entertaining to me than the actual meaning of “indigestion.” (EDIT: this is wrong, actually – thanks to @yamitenshi for the correction)
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Isn’t indigestion 消化不良?
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Shoot – you’re right; my mistake!
This is revolutionary, thank you. I don’t speak Italian but I know a few words from playing classical music (that’s one of them!).
For some dark reason, I personally love how 暗殺 (あんさつ) sounds. It is so fitting.
I know there are lots of other words I like for different reasons, but I can’t name them off the top of my head right now.
Edit I just remembered how I also love 確かめる (たしかめる) and variants of the verb like 確かに, etc. The rhythm and sonority of it hook me all the time.
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みゆき族, this word is so awfully specific.
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Maybe, 諦めないで sounds like, don’t get clear eyes or don’t open your eyes.
風船 is one of my leeches for the exact same reason…
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… and English!
Although in English it also includes the ones with very pointy teeth for making perforations in paper, it’s mostly used to refer to cogs.
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昔話 - Just sounds funny
お袋 - Sounds mean in English
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海王星 just sounds kinda cool. 
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言葉 was always a fun one to me. Nice to say, and word leaf is such a fun combination
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Last week I learned 孫の手 which means backscratcher.
But I originally read it literally as “grandchild’s hand”
I only learned that it meant backscratcher because I looked it up after being a bit confused by the sentence that I read it in, which I had understood as “I use my grandchild’s hand to scratch my back” , which felt a bit weird to me 
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My favorites were always the ones that seemed like someone forgot the word and just improvised. He broke his, what-do-you-call-it… hand… neck.
My new favorite also has to do with the hands - 手袋 (hand-bag). Dang, it’s cold outside, I need to put on my hand… uh, bags. (I actually say that in English now)
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I’ve always liked 手首 and 足首
first time I saw them I was like “oh yeah leg neck = ankle, sure I buy that”
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金玉 Is my favorite cuz I find it waaaay to funny.
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I often find words charming when I encountered them in a charming context. I love the word 説得 because it appeared in a manga where a boy wants to marry a girl, and announces this to her father before letting her know he’s interested. Since she’s sitting right there, pandemonium ensues. It ends with the boy saying 大丈夫、これから時間をかけて、説得します。
So. funny.
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A lot of words related to weather are quite fun as well, just this morning during my lesson with my tutor I learnt 雷 （かみなり）which feels like “God is making noise”, for Lightning/Thunder.
As well as 嵐 （あらし）because it is made up of 山 and 風 “a mountain wind” or “wind from the mountain”, for Storm.
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Second vote for mukashibanashi
Recently, I’ve found 冗談 (joke) to be quite fitting. Literally ‘superfluous discussion’.
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