The best way to scope out a new city? Walk it. And all the better if you can make it an arbitrary path.
Chiang Mai has an interesting design. The center, old city is a large square, surrounded by a moat and the remains of city walls and gates. This moat has since been built around by a divided parkway which encircles the old city and has some of the busiest traffic in Chiang Mai. This seemed as good a place as any to start, as most of the sights that the Lonely Planet guide points out seemed centered in this area.
One of the first things you immediately notice is the foreign influence. It likely isn’t the case, but just judging from the areas I visited, I would’ve guessed nearly a quarter the people in the city were foreign. It isn’t foreign influence in the sense that Bangkok is, where there is a noticeable attempt to create westernized atmosphere, with everything written in English along with Thai.
Instead, with Chiang Mai, it mostly retains its own national , architectural, and cultural qualities, while having an immense presence of foreigners which are catered to.
The streets are (inside of the moat, especially) a maze, and very easy to become disoriented in at first, as so many of the side streets look familiar. Walking around the outskirts of the moat and ducking in and out of the square, this becomes readily apparent.
Still, as long as you can keep some kind of bearing as to how to get back to the main road, this means that you will inevitably stumble across some interesting things as you’re going down streets you had no intention of being on.
There were hidden markets, some spectacular temples, and all around the city are hidden chedi made of the same masonry as the oldest parts of the city wall. These are always an unexpected please to come across stuffed in between a hodgepodge of buildings.
But, in this case, I believe pictures will do better.