When planning a trip to Maui, many people have visions of themselves driving along the coast with the top of their convertible or Jeep down. While this can be a fun way to explore the island, there are a few things to consider:

1. You will look like a tourist. Don’t care? You may be a target for a car break in. There isn’t much crime in Hawaii, but break-ins do happen. (I’ve actually seen one almost happen and chased them away.) If renting a convertible, don’t leave any valuables inside your car. Heading to the beach to snorkel and have nobody to watch your stuff? Consider keeping your wallet in a safe in your room and just bringing some cash or credit card you can keep on you at all times (Matt puts a credit card, a $20 bill and his ID wrapped in a rubber band in a pocket in his board shorts). You can also try the “dirty diaper” trick. Wrap your phone and wallet up in a clean diaper and leave in plain sight on your towel.

2. Depending on where you stay, it may rain a lot, even daily for short periods. (South Kihei/Wailea is your best bet for dry weather.) For that reason, I recommend putting the top up anytime you leave it for an extended time (even at the beach). Last time we rented a Jeep on an island (Tortola), Matt wouldn’t even take the sides down because it was such a pain to snap them back on. We needed a 4×4 on that trip because the roads were so steep. While it was fun to drive in, it reminded me how noisy and stiff a ride a Jeep is. Unless you are planning to do the full loop on the Road to Hana, you don’t “need it.” Consider your partner’s patience for these types of things before booking.

You may have been told to rent the smallest car you can fit in because gas prices are high and parking spaces are small. I don’t buy into this. Maybe it’s because we are from California where gas prices are already high, but I’ve never been shocked by the price of gas. Also, unless you are doing the full Road to Hana loop, Haleakala and the West Maui loop, you probably will only have to fill up once or twice. Remember, you are on an island! We usually rent a minivan or full size car (hubby is 6’7″), and we’ve never had an issue finding parking except for in Lahaina or Paia, but that’s because it’s crowded, not because we couldn’t fit in a spot.

SECRET: If you have kids or a large group, I highly recommend you rent a minivan if you can afford one. You don’t want to start your vacation off sweating profusely playing Tetris to get everyone’s bag in the trunk. Sliding van doors also do help in smaller parking spots and a large trunk is required to fit all the chairs, snorkel gear, sand toys, ice chests and bags for trips to the beach.