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Aloha Reader, Every single trip to Hawaii, I see the same thing: a convertible pulled over on the side of the road, top still down, rain coming in, one adult frantically Googling how to get it closed while the other tries to shield the kids. It's funny until it's you. Don't rent a convertible during rainy season. That's just one of the car rental mistakes I see families make over and over. Here are the others worth knowing before you book. Waiting too long is the big one. Rental inventory in Hawaii gets tight fast, especially in summer and over the holidays. By the time you're a few weeks out, you're paying a premium for whatever's left. Book as soon as your travel dates are set. Don't just go with whatever name you recognize at the airport counter either. I always book through Discount Hawaii Car Rental because they compare rates across all the major companies and the prices are almost always better than booking direct. They've also gotten me free extra drivers and reduced young driver fees, which adds up. On car size: a lot of families assume they need a Jeep in Hawaii. You really don't. The roads are paved, everything's accessible in a regular car, and Jeeps aren't cheap. That said, renting one can be a genuinely fun experience if it fits your budget. Just know it's a vibe, not a requirement. What you do need is enough room for your people, your gear, and the inevitable Costco run. I drove an SUV on my last trip and it was the right call. Before you drive off the lot, do two things. Walk around the car and photograph every inch of it, close-ups of any scratch or ding. I got charged once for damage that was already there and had no proof. And check the registration sticker on the license plate. Expired tabs on rental cars happen more than you'd think, and getting pulled over in a rental on vacation is not how you want to spend an afternoon. Summer rates are already climbing and availability on the most popular islands goes fast. Before you book anywhere else, check prices through my link. I've been recommending Discount Hawaii Car Rental for years because they consistently come in lower, and the savings are real. Aloha, Marcie |
I've visited Hawaii more than 40 times and I know ALL the tips and tricks for planning the ultimate Hawaii family vacation! I offer free Hawaii planning email courses. I also send weekly emails on Fridays where I share my top things to do in Hawaii with kids, the best family resorts in Hawaii, and my ultimate packing lists! Mahalo!
Aloha Reader, The first time we did an inter-island flight, I treated it like catching a subway. We showed up about 25 minutes before departure, bags in tow, fully relaxed. We made it. But just barely. And I spent the whole walk to the gate sweating through my shirt, which is not the vibe you want at the start of a Hawaii vacation. Inter-island flights are short (Oahu to Maui is about 25 minutes in the air) but the airport experience is completely normal. Security line, gate, boarding. Budget...
Aloha Reader, This is the question I get more than almost any other. Maui or Oahu? Which one should we do? And the answer I always give is: it depends on your family. Not in a wishy-washy way. In a very specific way. Because these two islands are genuinely different trips, and the right one for you has everything to do with what you're actually looking for. So let me walk you through how I think about it. You should probably do Oahu if: It's your first time in Hawaii. Oahu is the easiest...
Aloha Reader, I got an email a couple weeks ago from a mom who'd been planning her July Maui trip for months. Flights booked. Hotel sorted. She just hadn't gotten around to the luau yet. She wanted to know which one I'd recommend. I pulled up availability. Sold out. All of them. For her entire week. That's not unusual for summer Hawaii anymore. The window between "I should book that" and "it's gone" has gotten a lot shorter. If you have a trip on the calendar between June and August, some...