Planning a Family Trip to Hawaii

After a few snowy months, anyone else craving warm-weather getaways? I’m pumped that we already booked our next year-end trip with the kiddos to HAWAII. I’m here to share more about this favorite family destination, tips for traveling with littles, and how I found time for self-care through it all. 

Hawaii has been very special to us. Gus and I traveled there for our honeymoon and baby moon. During our baby moon, we splurged on the Four Seasons Oahu at Ko Olina. It happened to be located right along the beach with a few other amazing properties. While strolling with Maelyn in my belly, I hoped that one day we’d return for a different kind of trip — a family vacation at the Disney Aulani Resort next door. I felt extremely grateful to return with not one but two little ones post-pandemic. 


We planned (what I thought was) pretty far ahead and booked the last room available in July last year. Definitely a lesson on how early to plan out these family trips! We stayed December 28th through January 1st, and it was absolutely wonderful and let’s be honest, wild, with a 1 and 3yr old!

The first thing we did when planning was put reminders on our calendars for when we could start booking restaurant and spa times. This is such a simple way to make sure you get the places and specific times you’re looking for (especially when trying to stay on somewhat of a schedule for the kids). 


Next we did our research on childcare options. The hotel did not offer anything, however they recommended groups in the area. We went with Happy Kids Maui for 3 nights 6-9/10pm. I was a bit hesitant but ultimately it was SUCH a great decision. It allowed us to fully embrace the time with the kiddos during the day, then have time for ourselves after their bed-time. The first night, we literally just took the opportunity to have extra hands while we unpacked. The next night, we went for a long stroll and glass of wine. And the final night with the lovely Andrea (Maelyn still talks about her!), Gus and I enjoyed a phenomenal dinner at ‘AMA‘AMA, Aulani’s open-air restaurant overlooking Ko Olina Beach. Highly recommend for a date night. 

As we got closer to the trip, we built out an itinerary - it really helps keep us organized! For each day, we really only had 2-3 activities and/or reservations planned. We kept it simple and tried hard not to overplan the days. A few of our favorite activities were: Character Breakfast (highly recommend for the littles!) and the Mini Mani at the Spa (Maelyn absolutely loved this activity to kick off our NYE celebrations!) We also spent a LOT of time enjoying their many fabulous kid-friendly pools and building sand castles with their free rentals on the beach. 

When it comes to meal-planning, I loved investing in a room with a kitchen. For the most part, we cooked healthy, simple breakfasts and ate at Ulu Cafe by the pool for lunch with the kids (still dreaming about that fresh poke bowl, 80 degree weather, ocean view and family giggles!) 

In addition to making time for us as a couple, Gus and I are pretty good about finding space for each other to take alone time to recharge. For me, that looks like 15-20 minutes of walks and a little yoga/meditation along the beach. 

Hope that’s a bit helpful as you plan out your family getaways!