Depends on what kind of amenities you want nearby. Haven't been to all the islands yet but of the ones we've visited we probably had the most fun on the North Shore of Oahu. Though I don't care for the commercial aspect of Waikiki the drive up the coast to the North Shore is full of great little spots, and the North Shore itself offers a quiet reprieve from everyday life. We stayed at Turtle Bay, which was great but next time we'll probably rent a house – hopefully on the beach to maximize down time and surf time. If you're restless like me Oahu offers enough roads paved and otherwise to keep you moving. If you do the North Shore and don't know about it, a must stop is Kua Aina in Haleiwa – still dream about the best burgers and fries I've ever had….

 

We have been to each Island over the years and each Island has its own ambiance.

My fav is Oahu, its got nightlife and great places to eat and lots of stores and high end stuff.

If you want some R&R on Oahu its a drive away to the north shore but Waikiki is a hot place to stay.

Maui is too crowded for us,, too many cars and traffic jams.

Kauai is peaceful, easy, non commercial compared to Oahu and Maui.

Lanai is dead, ,2 hotels one on each end, not for me.

Big Island,, not for me. black sand.

Too bad you cant experience all of them and make plans to visit the one you like best next visit.

Cabman

 

What Dana said. Stay on Lana'i and spend a day on Maui.

I live here, I know.

Also, if you decide to stay on Maui, stay at the Grand Wailea, not the Four Seasons. I've been to both and Wailea provides a much more authentic Hawaiian feel.

 

If you are going for remote, Molokai it is. Beautiful island with very few tourists. Has the most amazing views. Went there this past Christmas/New Years. If you are not looking for a "get away from it all", it is probably not recommended.

Disclaimer: Been to Big Island, Oahu, Maui, Molokai, and Kaui.