Our Sixth Trip to Hawaii within 10 Years

Six times in ten years! I had to double check my emails to confirm the amount of times. We went in 2009, 2010, 2011, 2014, 2017, and 2019. Our most recent trip to Hawaii was quite memorable, and now that we’re back on the mainland, we’re already contemplating when we’d make our next return. Yes, it was tough with 2 kids (a 2- and 6-year old), but we still had a great time. And as many times as we’ve visited the islands, we were able to see new places and experience new things. In the next set of posts, we’ll share the hotels we’ve stayed at, the activities we’ve done, and some of the amazing places we’ve visited.

Planning the Trip

Planning this trip wasn’t easy. Making an itinerary with 2 kids isn’t as easy as planning a trip for 2 adults. As you know, there are different interests, and age restrictions. But at least we all share common interests – beach, good eats, and hiking. Once I figured out the islands we were going to visit, I was able to plan out what activities we’d do.

Another factor was duration. When visiting Hawaii, at least from the East Coast, we recommend booking at least a weeklong stay. Considering all the activities we wanted to do, friends we planned on visiting, etc – we booked a 2 1/2 week trip. A bit on the longer side than our usual 10 or 14 day excursions. The sweet spot for us is 14 days.

Flights

The flights were key. As tempting as it was to book a direct flight, likely via Hawaiian Airlines, I thought of how it would be for a 2 year old boy in a tight area for 11 hours. Eh, not a good idea. So I planned for 1-stop flight with at least 2 hours between connections to allow the kids to stretch, walk, eat, and get the wiggles out. After researching different flight options, I settled with American Airlines with a 2-hour layover in Dallas.

Interisland flights were booked at the last minute, actually the day we flew to our first stop. Not an issue as there are many flights available between islands with different carriers. One takeaway is consider using your frequent flyer miles to book the flights. An interisland flight costs around $85 depending on the airline. I managed to get tickets on Hawaiian Airlines using only 7,500 miles on Delta and a transaction fee of $5.60 per ticket. This was an easy way to save money, especially when paying for a family of 4.

Hotels

As we’ve learned on past trips – space is key. While getting a suite wasn’t in the budget, we were able to find reasonable sized rooms that allowed the kids to move around while not feeling cramped. Another requirement is laundry facilities. Yes, doing laundry with kids, and in a beach environment is key for us. We stayed at a total of 5 hotels, all in different areas of the islands we visited.

Cars

I usually wait until the last minute to reserve a car mainly because I don’t know my itinerary until the end. Why wouldn’t I know my itinerary? Knowing when we’d travel to the next island isn’t decided on until the end when we coordinate schedules with our friends on the islands.

While I looked at the usual travel search engines, frequent flyer gateways, employee discount sites, and more, I found the best deals via Costco. No, I’m not getting paid to mention that, but if you’re a member, check their website for prices, which change daily. I managed to save at least $100 on a weekly rental.

Keeping It Organized

With the hours of research and planning, I kept it all together with a large sheet of paper. Call me old-fashioned, but sometimes it’s easier using pencil and paper to jot down ideas, crunch numbers, plan itineraries in a grid view, etc. Once I nailed down the islands we’d visit, I moved it onto a Google Spreadsheet so I could work on it on my laptop and my phone, while collaborating with my husband on it.

How Did We Fare?

Overall, with a 17-day itinerary, the trip was great. While tough to plan, we didn’t have a hectic schedule and it was relaxing, yet the usual everyday family craziness still happened.

Do you have any family trip-planning tips to share? Do tell.