The Laihana/Kaanapali side of Maui is more down-to-earth; walk into small shops from the sidewalks, far more less-expensive casual restaurants to choose from, more foot and car traffic, and generally a bit more gentrified. The Wailea/Makena side of the island is bit quieter and a bit more upscale overall; There are a few good shopping centers, but there is no "Bourbon Street" "Bubba Gumps" sidewalk environment atmosphere to speak of. The area is less gentrified, less noisy and a little more quiet and exotic overall. If you are looking for "social/community energy" and nightlife, this is not the better side of the island for you. It's got more of a modern/upscale/suburbs vibe. It's a healthy 45 minute drive between the two ends, so you should carefully think about what type of environment you are likely to appreciate more. You probably won't visit the opposite area more than once. I personally prefer the Wailea side much much more, but a greater percentage of the masses who have been to Maui have probably been to the other side which is a little more economical on average. You'll love it no matter which choice you make.