I’ve been to 3 islands in Hawaii – Kauai and Maui (each for a destination wedding) and Oahu as the last leg on the Japan and Thailand trip with B’s family. Since we stayed in the touristy areas of Maui and Oahu, I thought most of it was pretty commercialized with lots of high end stores and a bit overpriced restaurants. Unfortunately, when we went to Oahu, it happened to be the anniversary of Pearl Harbor so I didn’t get a chance to visit it. I liked Kauai out of all of them since it was rustic and rural, and there were chickens everywhere just randomly roaming about.
There’s a running joke with my friends that since two of my girls got married in Hawaii, that I should also get married on another island since all three of us are fairly close. B would be into it, but honestly, I think destination weddings tend to place a huge burden on the guests. Don’t get me wrong, I’ve been to four destination weddings and while I absolutely loved vacationing with my friends or family, I’m not sure I could do that because I would feel kind of bad for the costs I put on to my loved ones. But, there is definitely a savings benefit from destination weddings (especially when people have huge families), so I can see it from both perspectives.
Hawaii is wonderful if you want to experience island life, but I think to experience rural island life, Kauai would be the place to go. Food-wise, I think Maui had some pretty good restaurants, and I loved the assortment of delicious poke available at the local supermarket. Oahu reminded me a lot of La Jolla, a bourgie area in San Diego, but we were fairly jet-lagged from all the travel that I don’t remember too much of it. I could easily see myself running a marathon at any of the islands, though – the scenery is fantastic, no doubt about that.