Is the drive around the island fun/easy to manage or would you prefer to stay at two hotels and limit the driving? Which would you find more ideal? We will be staying in December for 5 days.

Aloha Ashley - as a regular Kauai-goer, here's my perspective on your question: if you were going to be staying a week or more, I'd probably recommend staying on both sides of the island, but for 5 days, I think you can just pick one side for your hotel (probably best on the Poipu or east sides at that time of year), and just plan to spend a day or 2 of your visit exploring the north shore, which is a MUST to do, and quite frankly, still our favorite side of the island, even despite the rainfall there. The reason I'd recommend staying in Poipu or on the eastern shore is that there is more to do activity-wise within easier access from those points, aside from the usually better weather conditions. Have a great time, whatever you wind up deciding!

I say just stay put at one hotel. It only takes about an hour to drive to the north part from Poipu. Unless it is rush hour, which you may have to add 15 minutes. Poipu was nice because we had easy access to Waimea Canyon, fishing and snorkeling/diving. Plus the weather was really nice the whole time.

The only down side was the lack of restaurants (except for the ones at the hotels.)We ended up driving near Lihue a bunch of times for dinner.

Either side you stay...you will have a good time. It is my favorite of all the Hawaiian islands!

Ash24, This is one reason why we like to stay in the Kapaa area.
We apply the "30/30/45 rule"; 30 to Pville/30 to Poipu and about 45 to the West Side.

While not as "pretty" as Pville/Poipu, convenient so you don't have to pack/repack.
Driving on Kauai is nice...even the traffic jams are "ok" since you have such nice scenery. "Hang Loose"!
Agree with a'gator's comment on driving to Lihue from Poipu for dinner. We stayed in Poipu a few trips back and found ourselves doing that a few times too.
Driving thru the Tunnel of Trees is cool at night.

Hard to beat Kiahuna Joe's for b'fast, tho. Great scenery and a Kiahuna Joe's omlette with a jalapeno kick!

Margot, If you're a Kauai regular, would I be a Kauai irregular? ><

Kal - are you a Kauai "irregular"??? You're an "irregular" wherever you go!!!

Kal,
Where is the Tunnel of Trees??? Sounds cool!
Does anyone know of a website where I could book a few more nights at the Hyatt, even though the hotel says they are full. I booked 3 nights at the Hyatt through Hotels.com but they are also sold out now. Is there another website to check??? Right now we are staying 2 nights at the Sheraton and 3 at the Hyatt. If I can't get all 5 nights at the Hyatt, would those two hotels be close enough to be an ok arrangement(not too much of a hastle to change hotels?)

I would check the Hyatt site itself - I've found the lowest prices there, or on hotwire (as its the only 5 star hotel in that area, so you know thats the one)

AshTwoFour-You will drive thru the The Tunnel of Trees on the way to Poipu. A lot of eucalyptus and other trees overgrown in typical Garden Isle" fashion.

It was even mo' bettah before Iniki but it's about 100% grown back.
When we first went in '89, you had to turn your on during the day time when you drove through.

Margot-As long as I'm a "Kinky Village Irregular", it's OK with me!
Besides, those BIG bran muffins you can pick up at Foodland make me a happy guy!
:-"

The Sheraton and Hyatt are very close to each other, a five minute ride. So switching from one to the other would not be a hassle. Hyatt is the nicer hotel of the two, also the more expensive. Does have a great pool area and nice grounds. Sheraton has the best, swimmable beach. I'm a Poipu girl each February, but I also love the North shore for it's beauty. Just wish the weather was a bit better there in February.