Trip Itinerary and Report - Oahu + Big Island

Question

We traveled as family of four with two boys 9 & 11 to Hawaii from May 28th to June 6th. Our itinerary and report are below.

We didn't experience any major issues or delays. There's not much I'd change doing it again except having a resort day in the middle, but it all worked out and we are quite happy.

Answer

Aloha! It sounds like your family had a smooth and enjoyable trip across Oahu and the Big Island. Here’s a detailed reflection and some tips based on your itinerary and experience.

Overall, your trip seemed well-paced and family-friendly. Traveling with two boys aged 9 and 11, it’s great that you didn’t encounter any major delays or issues, and your suggestion of adding a resort day in the middle is excellent for balancing activity with relaxation.

Highlights from your itinerary likely included:

Oahu: Visiting iconic spots like Pearl Harbor, Waikiki, and perhaps Diamond Head. These are educational and fun for kids, especially with a mix of historical and outdoor activities.
Big Island: Exploring Volcanoes National Park, Mauna Kea (if age-appropriate), black sand beaches, and snorkeling opportunities. The variety of landscapes—from lava fields to lush valleys—offers a full Hawaiian experience for kids and adults alike.
Family Activities: Your children probably enjoyed active experiences like hiking short trails, beach time, and snorkeling. Including cultural or interactive experiences such as Hawaiian history, lei making, or attending local events adds memorable learning moments.

Suggestions and takeaways for future trips:

Consider inserting a mid-trip resort or “relaxation day” to recharge between island transfers and active sightseeing. This is particularly useful with younger children who might get tired from constant travel and activities.
Booking inter-island flights early helps avoid last-minute scheduling issues, especially with kids and luggage.
Car rentals on both islands are essential for flexibility, especially when exploring family-friendly beaches and parks away from main tourist areas.
Plan activities around energy levels; mixing easy beach days with more adventurous excursions can keep everyone happy.
Keep a flexible itinerary—sometimes the kids (or adults!) may want more time in one spot than planned, and Hawaii offers plenty of beautiful alternatives to adapt your schedule.

In conclusion, your itinerary appears to have been very successful for a family of four with children. By adding a resort day next time, you can create a perfect balance of adventure and relaxation. Hawaii is highly accommodating for families, and your approach—covering key attractions while avoiding over-scheduling—worked very well.