We think yes. The island has SO much to explore that it might feel limiting not to have one. Shuttles can be set up, however, we think to maximize your time there, one car per party will work best. Uber is getting more popular, but due to the quiet and relaxed energy of the island, it is not a reliable way to get around.
Listen up...it will rain every day. BUT, do not fret! Kauai is a tropical island, so rain is inevitable. When you’re there it will be mostly sunny, with slight clouds. Every once in a while (usually once a day or so) rain clouds will roll through really fast and provide a nice, unthreatening shower. It’s usually not even enough to make you get off your beach chair and feels quite refreshing. Within 2-6 minutes it will pass and the sun will be shining again. For this reason, if you are checking weather apps, they will almost always show rain in the forecast. But don’t let it bum you out because it doesn't mean it's going to rain all day as it would in Chicago.
Kauai is very casual. If you think you might be too dressed up, you probably are, especially on Kauai. Seriously – even a wedge heel is too much. Don’t bring them, unless it's for your wedding outfit. As soon as you get on the island you’ll feel this incredible informality that is so welcoming and a real “come as you are” energy. It’s really beautiful. Kauai is not a ‘scene’ as some other areas of certain islands can be. It’s all about being comfortable. You can essentially walk into any establishment like you just came off the beach and feel comfortable.
Kauai is called the ‘Garden Isle’ and once you arrive, you’ll understand why. It is SO lush with plants and vegetation. It is HEAVEN. You’re going to feel like you are on another planet...or in Jurassic Park. Compared to other Hawiian islands, Kauai is very undeveloped, and locals really want to keep it that way. They have a rule that you cannot build anything over the height of a palm tree. Awesome, right? Because development is so minimal (done intentionally to protect the lands and coastline) only one side of the island is built out. So all of the towns and roads are on the east-ish side. The side that isn’t built out is essentially all the NaPali Coastline. I would split the main ‘towns’ of the island into three areas: Poipu, Lihue, and Princeville/Hanalei. There are many in between, but these are the three big ones. Explore the island! There are great little towns all over the island, each with their own unique look and feel.