As a part-time resident and long time visitor to Maui, if there’s one piece of advice I’d offer to someone packing for a vacation to Maui it would be to pack lightly. One of the most wonderful things about Maui is how laid back it is. One can go into virtually any restaurant and store dressed very casually. Indeed, throwing a cover up on over your swim suit makes you virtually dressed up! The weather is also on the whole very consistent meaning that a couple tshirts, shorts, swimsuits and perhaps a sweatshirt and/or sweatpants if you tend to get chilly is about all you need. Staying in a condo like ours that has a washer and dryer eliminates the need to drag along excess clothes.
Should you want to dress up for a nice dinner, guys can get away with a hawaiian shirt and khaki shorts while a woman would be considered dressed up in a nice sundress. 99% of the time here I wear flip flops, saving athletic shoes for situations like hiking, running or going to the gym. A lightweight rain jacket is handy for the occasional showers you may encounter.
Be sure to bring your sunglasses and a hat; sunscreen is an essential item but can easily be purchased here. I’d also suggest bringing a bag to use as a beach bag – definitely going to be carrying sunscreen and water with you to the beach.
Save yourself the checked baggage fees – or if you must bring a big bag, keep it mostly empty and load up on the souvenirs!