I've been touring a lot the last years and especially on the mountains but in the cities as well. I have a 5 years old tent but I 've only used it once, when I went touring with my sister and she didn't like the idea sleeping without a roof. I sleep on a z-lite matress with a sleeping bag and a inflatable pillow. It's so much more than just sleep when you do it like this. You have the stars above you, smells, and a very soft breeze (or a very strong wind-depends).
I've slept besides rivers, mountain peaks (lots with crazy winds and crazy cold), city ports, abandoned houses, house gardens, city squares, stables, historic forests, castles, ghost towns, ruins etc. Everywhere. I do encourage you to try it, you will remember my name!