We had a fantastic family trip to Hawaii in the summer of 2017. We had so much fun we planned to return in 2018 and had the trip all booked when we had a last minute conflict that caused us to cancel that trip. We were disappointed but kept the faith we would find the time to return soon. When we started planning for summer of 2019 we decided Hawaii was the place we wanted to go.

Island Hopping or Not?

In our first Hawaiian family trip we spent the entire time on Maui. While we had a fantastic time, we wanted to explore a different island first and spend the end of the trip on Maui. We narrowed our choices to the Big Island and Kauai since my wife and I had been to Oahu (where Honolulu is located) on a previous trip before kids. Ultimately we decided on the Big Island in hopes of seeing a volcano in action!

Timing

Since we we were looking at two islands, we’d plan for a two week long trip plus or minus a few days based on availability. We’d plan for 4 or 5 days on the Big Island and 9 or 10 days on Maui (we really loved our last trip to Maui).

We’d focus on using miles for the trip and points for hotel stays where it made sense. We’d be focusing on Marriott properties to leverage my wife’s status and perks and utilizing all the points we’d been earning over the previous year. We’d plan to leave after school ends and have the trip include the 4th of July to take advantage of a work holiday. If we’ve learned anything from our travels it’s that it’s always best to maximize the vacation days you get each year!

What to Do?

From our previous trip to Maui where we had such a fantastic and relaxing time, we knew what we wanted to do to fill up the time there. There were some things we didn’t have a chance to do last time that we would try to fit in, but this trip was targeted to be a much more relaxing trip than some of our recent trips.

We had never been to the Big Island so we were going to be many more firsts to explore there. Depending on flight availability we’d try to do that island first. Relaxing at the end is generally how we prefer to plan our travel.

With two weeks in paradise set aside it was time to work on the details and logistics.