Furthest I’ve been (until now) N: Helsinki, Finland 🇫🇮 S: Tétouan, Morocco 🇲🇦 E: Kyiv, Ukraine 🇺🇦 W: Montreal, Canada 🇨🇦

N: Husavik, Iceland (And, by ship, just North of the Arctic Circle) S: Caracas, Venezuela E: Tokyo, Japan W: Maui, Hawaii

Now that I see your North and West entries, I had to check - Montreal is not as far north as Tallin, so my farthest North and East items should have been the same!