Definitely go to Maui and stay on the north west side of the island (near Lahaina). Some of the nicest beaches are up there, including Flemings, Napili, and Kaanapali. My recommendation to people going to Hawaii is to rent a vacation condo. These are around $1000 to $1500 a week for a 1 bedroom or 2 bedroom condo right on the ocean, with a full kitchen and often in-unit laundry. The best place would be in Honokowai or Kahana, about 10 miles north of Lahaina. And, the waves aren’t that big on the west side of Maui.

There’s a couple shopping centers where the Lower Honoapiilani Highway cuts off the main highway, so you can buy all your groceries and anything else you may need there. This actually works out to be a lot cheaper and more convenient than staying in a hotel, where you would have to go out for every meal. And, if you’re staying some place like Kaanapali, every place is expensive to stay and to eat.

In Kahana, there’s a strip mall with a couple of good restaurants. I think the best one there is the Maui Brewing Company. They serve beers that they brew on premises and have really good food. There’s also a Roy’s and a Black Angus steakhouse there.

This area is also close to Lahaina, where all the night life is. Lahaina is an old fishing village, but there’s lots of restaurants and bars there, especially along the water front. I wouldn’t recommend staying in Lahaina. It’s kind of noisy and crowded, and a nice place would be expensive. But, you’re only about 15 minutes away from Lahaina in Honokowai or Kahana.

Each of the Hawaiian Islands has its own personality and character. So, knowing what type of person you are and what you like to do will help you decide which of the islands you will like.

If you like tourists and fishing you should like the Kona area of the “Big Island” of Hawaii. If you like solitude, a tropical feel, a rural atmosphere and you don’t mind rain, you should like the Hilo area of the Big Island. The west side of the Big Island has a few nice small beaches,
including black sand beaches. Near Ka Lae, the southernmost point of the island you will find a green sand beach. Big beaches are not prevalent on the Big Island.

If you enjoy scenery, hiking, snorkeling, kayaking or surfing and don’t yearn for “night life” then the oldest of the islands, Kauai is for you.

If you are the kind of person who keep a bathing suit, snorkel gear or a surfboard in your car, then Maui is for you, because it has 120 miles of easily accessible and swimmable coastline, more than any other island.

If you have an artistic temperament or perhaps you like to get away and write, then seek out the island of Lanai.

If you love nature, hiking and solitude, then “the most Hawaiian” of the islands, Molokai is for you.

You’ll enjoy Oahu if you like beaches, shopping, tourists, high-rises, traffic and don’t mind a lot of other people. Honolulu is like a tropical version of NYC, or LA as it was in the smog-free 1950’s.

Go to Oahu, not overdeveloped in the mainland sense of the word

I would recommend Oahu or Maui. Oahu has the very busy city of Waikiki to walk around, shop at, and the beach is within walking distance. You can also go to Haleiwa which is on the opposite side of the island but a lot of tourists go there too! There’s a lot of good food there, although it’s not a very developed part of the island like Waikiki. But I would say you could get a “Hawaii flavor vacation” there!

Maui — I’ve only been there twice but everything is so beautiful! I don’t know in depth details about Maui but if you do decide to go there instead, you will not regret it.

I would recommend Maui. I always stay in Lahaina and it is a great time. It is about a 30-45 minute drive from the airport but it is well worth the drive and has great scenery on the way. It is a small town with some shopping and a great night life. The main street is right on the water and is lined with restaurants and a few great bars. There is a Hard Rock that always has some local music at night. Kaanapali is the next town over (about a 15 minute drive) and they have hotels over there as well. You can also get to some great secluded beaches for some snorkelling or hike up to a waterfall with a short drive. The waves aren’t rought at all and are great for learning to surf on.
Hope this helped a little bit… Have a great trip!

Maui is the best. They have beautiful scenery, yet they have the night life and typical luau stuff if you want. In Oahu it is expensive to rent a car to get around and if you use the bus system, it takes a long time.
In Maui you need to rent a car, but they are not overly expensive. They even have rent-a-wreck there. Good Luck, and aloha.