Does anyone know much about where I will be staying, Kailua, on the windward side of Oahu? What to do? Where to eat? How does it compare to staying in Waikiki? Should I reconsider?

Kailua has a very nice beach. We usually go there for a swim day while on Oahu, but like staying in Waikiki. It all depends on YOUR preferences. Do you want to shop? Walk to restaurants? Use free or easy/cheap transportation? Do you want solitude? Just to walk the beach? Golf? Answer these and you've answered your own question! Also, how long will you be there?

Kailua on Maui is upper middle class residential area. The beaches are beautiful but usually windy, which is why they're the windsurfers' favorite place. If you want nightlife and lots of places around you, you might want to stay in Waikiki. If you want quiet and solitude, you're probably better off in Kailua.

ummm....Kailua is not on Maui, it's on Oahu. There is a beach there called Lanikai, which was once voted one of the most beautiful beaches in the world. Kailua is a pretty place and if you are looking to just relax, golf, beach, or hike, then it's OK. However, there isn't much shopping. Like the previous poster said, there's not a lot of nightlife, either! But it all depends on what you want to do.

Sorry Norma, this won't help you but Lanikai Beach is what I dream of when I dream of my not-so-imminent retirement.

My husband and I spent 9 months living in Honolulu last year. We lived just below Hanauma Bay in a very nice rental house. It was my preference to drive to Kailua and Lanikai Beach over anywhere else. It's a quaint little town (Kailua) and Lanikai is a one-way loop (about 2 1/2 miles) of private residences...the more expensive ones of course are on the ocean side. There are entrances to the beach between the houses. There is no comparison to the beach at Lanikai and the beach at Waikiki. Lanikai is not crowded at all! There are several little restaurants in the town of Kailua...Mexican, Chinese, Italian and soul food in a little restaurant at the bowling alley. Definitely not the hustle and bustle or the fancy, expensive dinners of Waikiki. Just depends on what you want.

Norma, my family and I have stayed on Lanikai Beach four times in the last four years. It is my idea of heaven on earth. Yes, there is a breeze but it keeps you from burning up. No, there isn't the nightlife or shopping of Waikiki but that is only a 30 minute drive away. What you will have is lots of beautiful uncrowded beach and a welcome lack of tourism. Rent a kayak and paddle out to the Mokulua Islands. We like to eat at Bueno Nalo for Mexican and Buzz's is fun for cocktails and surf and turf. Mostly we like to get take-out or go to the Daiei and buy some fresh fish to throw on the barbeque. Enjoy! I'm green with envy.