The Island of Maui
Maui is relatively easy to get to. It is one of the main Hawaiian Islands. It is the top tourist destination together with Oahu. Honolulu is worth visiting (before we moved to Maui, we often went to Honolulu and stayed in Waikiki for a night or two before we went on to Maui). What makes Maui very attractive is that it provides more of an "island feeling." Once you get past Waikiki, Honolulu is a very "normal" big city. Maui is more in line with what people think of when they think of a tropical island. There are other islands in the chain of course, but they are less visited. "Big Island" is another destination of potential interest, but although bigger, it has a smaller population and fewer things of interest to visitors.
Maui has a few areas of interest for tourists. Kihei and Lahaina (on the south/west shores) are the main destinations. The North Shore is also a prime destination but may not have much appeal for short-term tourists. The North Shore is rougher and a great place to be for adventure seekers and extreme sports enthusiasts. We love going to the North Shore, and it is less than half an hour to get to the main North Shore destinations by car, but it isn't where we usually take visitors, since most people (especially families) don't enjoy getting mangled by 15 foot waves (or more).
Kihei is on the "friendly side" of the island. It provides access to great beaches everyone loves. Kihei is also in the middle of the island. This means you can get just about anywhere we want to go in 30 minutes or less.
Getting to Maui
Getting to Maui is surprisingly easy. Major US airlines fly into Kahului several times a day, usually from places such as L.A., San Francisco, or Seattle (so those may be your layover airports). If you want to spend a night in Waikiki, you could also fly into Honolulu first and then use one of the local airlines to fly into Kahului (avoid the smaller Maui airports). This is the more expensive option though, so we recommend you fly directly into Kahului. Honolulu does have more direct flights from more US airports though, so it is probably mainly a choice of where you want your layover to be.
Once you land in Kahului, the condo is only 20-30 minutes away. The airport is small, so you will be out of there in no time. You can then take a taxi or rent a car (see below). It is quite straightforward. :-)
Getting Around On Maui
People often ask us whether they should get a rental car. It probably isn't a bad idea. You will find the usual US car rental companies right at the airport, and the whole affair is simple. Maui is part of the United States and therefore, driving around will feel just like driving in any of the other US states or even most parts of Europe. Prices aren't cheap (this is Hawaii after all, and tropical island paradises are never cheap), but they are not outrageous either. You can also rent SUVs, which is generally a good idea if you plan to rent any equipment such as surfboards or windsurfing gear. Note that it is almost impossible to get a roof rack, and when you talk to rental car companies, you usually don't actually get to talk to the local office, so they know nothing about transporting gear. I noticed, however, that I usually don't need a roof rack. Most SUVs make it possible to open the rear window and just stick all your gear in the back.
But what if you just want to hang out in Kihei? Do you need a rental car? Truth be told, you can probably do without one. You have an awesome beach across the street from the condo and you have shops and restaurants within easy walking distance. The occasional trip to Lahaina you could probably do in a taxi. Of course you would miss out on the ability to just explore the island and find your dream beach on your own...