As the opposite of a HI virgin, I can give my opinions on the courses I've played:
Kaanapali North - Overpriced course behind the Marriott b/t Kapalua and Lahaina. I've played this course twice, as it is within walking distance of the hotel, but it feels like Florida, the course is surrounded by houses, and there is only one green located near the beach (and next to a public access pt. no less). Not to mention I it was $135 last time i played for this less than ideal situation. I heard rumors of someone doing the course over though....
Kapalua Plantation - Not much to add what has been said on here, the best course in Hawaii currently (sorry Nanea, barely anyone sees you). It's a big ticket course ($250+) but totally worth it.
Kauai Lagoons Kiele - A nice Nicklaus design that plays along the bay next to the Kauai Marriott, a few good holes, a healthy number of blah, resorty holes. Apparently this course will soon be changed, possibly for the better. The 13th is a great par 3 playing over the edge of the cliff, and the oft-photographed 16th is a short par four that is loved/hated due to its great views of the bay and lack of fairway.
Kauai Lagoons Mokihana - A solid yet unspectacular secondary course, less challenging in flashy than its sister. Some holes are almost alarmingly close to the Lihue airport runway.
Kona CC Alii Course - The Montainside sister of the more well-known Ocean Course. This course is short and hilly, playing among lava outcroppings. The most known holes is the "sunset hole," a downhill par 3 near the end offering views of the coastline. If you were to choose this club, I'd probably play the seaside Ocean course.
Poipu Bay GC - Site of the Grand Slam, wind is a huge factor. The course plays as a semi-benign resort course until the final 5 holes. 14 plays straight uphill to the top of the course before the final 4 tumble downhill to the clubhouse, combining great ocean views with the ancient hawaiian heiau ruins.
Princeville - I wasn't a huge fan of this course. Several holes were challenging and strategic, while more were too penal and just not fun. The course probably has the hardest opening tee shot I can think of, and several others that border on ridiculous. The rainforest in the interior of the course is beautiful, but you really can lose your ball (without even the option of a search) on about 90%+ of full shots here.
Pukalani - This course is on the slopes of Haleakela on Maui, and the climate is different about 2000 ft. above the valley floor. The course is one the locals would recommend, cheap and fun. I wouldn't recommend those looking for architecture visit Pukalani, but it is different than the resort courses along the coast. There are some beautiful views from the course, as well as a par three over a ravine that offers the option of playing to a second green at the bottom if one doesnt want to make the carry.
Dunes at Maui Lani - Another local favorite, a cheaper option to the resorts. There are parts of the course that have the Australian look to me (I haven't been there, but it appears slightly arid and firm and fast). They bill it as a links course, which is not true at all. There are a couple of great holes, and a few stinkers mixed in.
Wailea Gold - site (or former site) of the Senior Skins Game, the course is beautiful and finely manicured. It has views of Molokini, where many snorkling trips go, and provides a good challenge. I have not seen the other two layouts here, but I wouldn't think they'd be better than the Gold.
Wailua Muni - The course has gotten more press from hosting the publinx and being reviewed by Whitten a couple years ago. It has become more crowded with tourists looking for the "hidden gem" that will not set them back $150 like the resorts, and the course is not exactly the next Bethpage. Despite all of this, it is a fun course for about $50, that gives a good feel of Hawaiian golf before mass tourism.
One other thing to note, there is a deal we once used called the "Kauai Challenge" that combined rounds at Kiele, Poipu, and Princeville for something like $325 pp (in 2003). Not a bad deal considering individual rounds at highest price would add up to something like $425-450 pp.
Happy Hunting!!