This might be an interesting place to start - I found it by googling "which hawaiian island".

Lots of info including sites with free brochures for all islands:

http://www.fodors.com/community/united-states/first-trip-to-hi.cfm

The islands are each unique, so start with determining which island(s) best suit you. For me, the quiz at http://www.hawaiigaga.com/best-hawaiian-island.aspx is quite accurate.

As far as books go, I like the "__(Island name)__ Revealed" series. If you are wanting hikes and more do it yourself nature info the "Trailblazer __(island name)___" books are good. Not all hikes are really long.

Next determine how long you plan on staying and when...Post that information along with the island(s) you plan to visit as well as a description of your interests and you'll likely get plenty help on here. There are many many posts about the Hawaiian islands, so searching the forum is a good idea rather than reposting the same question asked a million times.

I wouldn't plan on spending less than five days per island that you intend to visit. Depending on the length of your stay and your pace, you'll want to make sure you are planning some relaxing/laundry days, too.

Hey, I tried out that survey that Mrkindallas recommended. It was fun to do and, I agree, pretty accurate. It also makes you really think about what you like on a vacation. Thanks to Mrkindallas for sharing this site.

I was in a similar situation, my first trips to Hawaii. It is a bit tricky to plan. I started by checking out a PILE of guidebooks from the public library, and read up about each island (and looked at the photos). I think the internet is terrific for moredetailed planning, but find it a bit overwhelming at the very beginning stages. A matter of "too much information".

Everybody has their favorite islands! Mine is the Big Island, where I live part of the year.

The questionnaire above always bugs me because it is almost impossible to get the Big Island as an answer, and one reason is so many of those questions address lodging.

The Big Island is so big and diverse that people have a passion for it, but it will involve a lot of driving and planning to see it all. It is largest, has the fewest people, is the most extreme geographically, has lots of historical sites, many charming heritage towns, coffee country, whales, gorgeous deluxe resorts and lots of funky b & b's, great restaurants, local music and festivals. Snorkeling is great, but there are fewer great beaches, although there are some for sure.

Kauai is gorgeous and green. It's much smaller and easier to get around.

Maui is also gorgeous and has more of a touristy atmosphere and nightlife.

Oahu, well, for me it's too congested, but it was the first island I visited, and it was lovely.

So, the answer is: you will love them all!

I think Maui is a good "starter" island, though.

I agree with Kailani when he says that Maui is a good "starter" island since it has a little bit of everything a visitor might enjoy.

I agree about Maui for a first trip! It looks like the Hawaii in the movies to me. Maui was my first island (when I was invited to a family reunion). On my own, I've chosen Oahu the last three trips.

We are also planning a trip to Hawaii for our 25th anniversary. We are going June/July 2010. We own some timeshares and I've been able to book 1 week on Oahu, 1 week on the Big Island and 1 week on Maui. I'm so excited - 3 weeks!! I guess we'll save Kauai for another trip.

We're in MA so it's a long flight and we wanted to make the most of it. I bought the "Revealed" book for each island, so between those and this site, I've been planning like crazy. Now if the airfare would come down a bit, we'd be all set. Good luck!

We did the islands for our 25th and planned a fun 4 island whirlwind... start in Oahu on Waikiki and be sure to visit Duke's, the North Shore, and Pearl Harbor...

Next stop Kauai for a helicopter trip and the natural beauty of the Islands...

Head to the Volcanoes on the Big Island, have some kona coffee and take a guided tour...

Finish on Maui near Laihana, grab a Luau, a day snorkel...

Its the best trip we ever took, no where near as hectic as it looks and this Island Sampler gave us a taste of where to go back next time....

We celebrated my birthday with a trip to Hawaii last year (50). Much like you, and for similar reasons, planning it was challenging for us as well. My husband actually got involved in planning this one. We wanted to make the most of our time there and each of the islands offer so much to do and see that it was difficult to rule any out. Worked best for us by developing a “wish list” for each island, prioritizing our islands based on what we wanted to do/see, and developing several draft itineraries – quite an endeavor.

We ended up choosing Hawaii and Kauai for the bulk of our stay (12 days total). We did fly in and out of Oahu in order to see Pearl Harbor.

Here’s an overview of our trip:
Oahu: Two nights. Stayed on Waikiki near the Beach Walk development – upscale touristy shopping and a number of restaurants to choose from. Went to Pearl Harbor and the battleship Missouri.

Flew to Hawaii. 3 nights Spent the first 2 nights on the East Side at a B&B. Spent one day at the Volcanoes Nat’l Park and drove to Punaluu Beach to see the black sand and sea turtles. Had a surprisingly good meal at a “pizza” place in Volcano Village. Spent a day driving to the Kona side of the island. The drive provides quite a number of different views and landscapes – Hawaii is quite diverse. Not to be missed: the scenic drive detour (near the Botanical Gardens) and the Botanical Gardens (we spent a couple of hours here). Akaka Falls was pretty cool as well. We didn’t get a chance to explore the Kona side – hadn’t allowed enough time. Note: We flew in and out of different airports here returning the rental car to different location – no impact on intra-island flight costs and minimal impact to rental cost – well worth it for the drive and the time we saved in not driving back. A good website for the Big Island: http://www.letsgo-hawaii.com/

Notes: We did not allow enough time here – I didn’t realize how much we’d like this island and how much there is to see. Also, the Hilo side of the island is pretty wet/moist. The B&B was very nice but without AC (needed for humidity removal not cooling) everything is damp.

We finished our stay in Kauai. 7 nights. We stayed on the North Shore (Anini Beach house rental). Not many dining choices but a good grocery and we prefer to stay in most nights. Lots to do on Kauai: Kilauea Lighthouse; Waimei Canyon State Park (nice drive and views – go early to avoid p.m. clouds and showers); Na Pau Coast State Park and the Na Pali Coast; this is THE place for a helicopter tour; easy to view waterfalls (Wailua and Opaeka’a); and Poipu area and Spouting Horn.

Notes: The north side of the island gets a lot of rain and again, nice place to stay but no air, so it was damp. I’ve a friend that stays in the Poipu area and loves it – drier side of the island.
For general Hawaii info, I found this website very helpful:
http://www.hawaiiweb.com/
Hawaiian Air offers a number of flights and prices were really reasonable when booked online in advance.
http://www.hawaiianair.com/Pages/Index.aspx

As for books - ashamed to admit it, but - I acutally got a lot of info/tips from the "Dummy" book.

By the way, we ruled out Maui because we seemed to have so much of what it offered (beaches, waterfalls, foliage) covered; we aren’t big on resorts/restaurants; and we had a beautiful/diverse drive on Hawaii.

Just planned a big trip for my husband’s birthday (60) – Grand Canyon, Arches, Canyonland, Bryce, Zion, Kodachrome, and Vegas. Brought back memories of trying to plan Hawaii!

Enjoy!

Maui is the place for you!

Kauai is a pit. Too hot. Too wet. Too boring. Too many bugs. Too much traffic.

we went to kaui and the big island last summer. we really enjoyed comparing the oldest and the youngest islands-agree with nettieL's plan