Kailua / Windward Oahu
We just returned from a week in Kailua, which we HIGHLY recommend if you're looking for a low-key (read: non-Waikiki) experience. Our ocean-view cottage was reasonably priced and we loved having our own beach on a quiet street (and no streetlights - a revelation for those of us used to always-bright city living).
Pinky's became our de facto hangout. Overall, I'd give the food about a 6.5 - 7, but the pupu (appetizer) selection was good and the menu had something for everyone in our rather diverse group. The specialty drinks have a nice kick and come in giant Henry the Eighth-sized goblets. We were also impressed with the staff - everyone was friendly and the manager quickly remedied a minor problem. By the end of our trip they knew us and we hated to say goodbye the last night.
We also visited Buzz's twice. I ordered local specialty fish and they were wonderful, and the others in our group very much liked the steaks. Beware of the Mai Tai's - they're strong like gasoline and pack quite a punch.
We did breakfast once at Boots and Kimo's and very much liked the famous macadamia nut pancakes. My husband was also pleased to find guava juice on the menu. We'd heard mixed reviews on the food and wait times, but an 8am weekday visit was just fine.
We ended up frequenting Agnes' Portugese Bakery. The pastry selection was wonderful, the coffee was hot and plentiful, and the place is spotless. It looks like a family-run operation and we just loved it. We didn't get the try the malasadas, but when a family with several small children came in they were all shouting "I want my malasada!" so we figured that meant something special.
We also stopped at Breaker's in Hale 'iwa during a rainy day on the North Shore; again, the food was just a bit above average but the friendly staff made up for it.
My sister reported good things on Romy's and Giovanni's shrimp trucks in the Kuhuku area. Note that Romy's is actually the only one in that stretch that uses locally grown shrimp.
Lastly, a big plug for the Kalapawai Market just north of the Kailua public beach. Surprisingly large beer and wine selection, and our 2 experiences with their deli sandwiches were excellent.
We're already planning a return trip!
We stayed in the Kailua for a week as we were getting married nearby Waimanalo Beach. I love staying in Kailua...it is so laid back. We had breakfast at Boots & Kimo's, it was awesome! I also went to Agnes bakery to get some fresh baked goods, but I don't think I got malasadas. I will have to try that when I go back. We didn't go to a lot of the restaurants nearby, we rented a house with a bbq grill, and we bbq'ed almost everyday. Oh, I miss Kailua!
I agree with you 100% about Kailua/Windward side. I've gone there almost every year of my life (my Tutu lived in Kanehoe until she passed away 2 years ago). My family rents one of Pat's beach cottages for a week. Every morning my husband and I get up at 5:30am, watch the sunrise over the Mokulua Islands, and then head to Kalapawai market for fresh coffee. Their Island blends can't be beat! The sandwiches are fantastic and really hit the spot after a morning on the beach. A fun treat is the Island Snow shave ice just up the road in the little minimall. Kailua is definitely a more laid-back, quiet version of Oahu, but I wouldn't have it any other way!
Lived in Kailua (Lanikai) in my teens too many years ago. Agnes' Bakery did not exist when I lived there but I never miss it when I visit now. Their Malasadas are the best I've ever had anywhere. They make them by order only-takes about 10 minutes but well worth the wait!
Call ahead to Agnes and the malasada's will be ready when you arrive. They are the best we've found on the island.
So far no mention of one of our favorites: Saigon Noodle Shop in Hidden Lake (just south of Kailua). Great food, very reasonably priced. Mainly locals eating there.