drsh99

Hi all,
We're planning 8 days or so in Hawaii with our 19, 15 and 10 year olds. We'd love some advice on which island and what activities as well as tips on finding least expensive flights from Chicago. We are looking for a 2 br condo or house, doesn't need to be on a beach, but nearby and would like advice on how to find (other than vrbo). Here's some detail to narrow the advice:

vacation focus is relaxation, beach time, water sports, biking/ hiking
we all love the outdoors
not big shoppers
not foodies, but would like a couple of nice dinners without the kids
do not want rainy weather (I heard one of the islands is rainy that time of year, not sure which one)

All advice welcome!

drsh

Placename

Maui is a good choice for your wishlist. The Ka'anapali area has plenty of condos, beach, and acess to restaurants and some shopping to be done independently, without the need to drive.

The rainy areas would be Kapalua and Hana on Maui.

lcuy

The windward (NW) side of any of the islands will be the most likely to have rain in December. But you never know, it could be totally sunny or rain on the south sides as well. The good thing is that usually if it is raining, you can drive a few miles and find sun. Plus the rain is normally pretty warm! North shore Kauai is the most likely place to get wet

least expensive flights are usually to Oahu, especially at Christmas. Waikiki will also have the least expensive lodging, if you will have a car, there are lots of hiking& water sports (plus the big waves on the north shore) on Oahu. Big island is probably the best for biking.

Dukey1

Some of the beaches on the Big Island AND on Kauai are rocky. For the most extensive degree of things to see and do besides staring at the water, I would stay right on Oahu. Great beaches, plenty of diversions for those children, too. I realize this does NOT fit in with what a lot of people here think is "the" Hawaii experience but given what you have to deal with I still think Oahu would be best for you.

suze

You can do all the things you list on any of the islands. I think Oahu is a good choice, and as already mentioned usually has the cheapest flights, and definitely has the most lodging options. Maui would be my second suggestion. I think with 5 people you'll want a rental car any island (although you can get away without one on Oahu).

sf7307

Do you love the outdoors as in hiking and totally laid back and quiet (Kauai) or as in beaches and sun and never having to put on pants or a jacket, but still having decent restaurants and a little "activity" around (Maui)? I do think a lot of teens would be pretty bored in Kauai. Since you plan to rent , I'd look at the Kailua/Lanikai part of Oahu (gorgeous beaches, a town, ocean kayaking, none of the glitz of Waikiki, but only about a 30 minute drive. I'd rent a car for the whole week, and go to the north shore ( just the drive acros the island from southeast to northwest is spectacular), Diamond Head, Waikiki, Hanauma Bay, etc.

drsh99

Great suggestions, all! Although three of us are outdoors-hiking-biking rustic locale types, our two teens will want more activity plus the kids want to see Pres. Obama's high school and the USS Arizona. So, it seems Oahu is the best option. I like the Kailua/Lanikai option. Maybe we can find a VRBO, too.