We split our Hawaii time between Oahu (4 days) and Maui (a week). Oahu was a mixed bag for us — busier and more commercial than expected. Maui was the real highlight. Both islands benefit from using AirBnB to stay with locals who can point you to the right places rather than the tourist circuit.
Oahu With Kids
- Good as a landing pad but crowds and traffic can wear families down quickly.
- Best to front-load it and move to Maui while energy is still high.
- Local beach spots far from Waikiki are where the real experience is.
Maui Highlights
- Humpback whale watching (December–April): roughly half of all North Pacific humpbacks gather around Maui to breed. A boat trip here is one of the most memorable things we did with kids anywhere.
- Haleakala crater hike: one of the world’s largest dormant volcanic craters. Go prepared — weather changes fast inside the crater and you can get caught well below the rim.
- Ka’anapali beach: sea turtles swim close to shore here. We snorkeled with them from the beach and did the famous Black Rock cliff jump.
- Road to Hana: 600+ hairpin turns, 59 one-lane bridges, and a real motion sickness risk for younger kids. Worth it if you take your time and stop often.
- West Maui drive: desert landscapes, lush valleys, and good viewpoints in one loop. A full day out from Haiku or Lahaina.
What We Would Do Differently
- Skip the Road to Hana as a single long day — break it with an overnight stop.
- Book whale watching early; tours fill up fast in peak season.
- Base yourself in a quieter area like Haiku rather than the main resort belt.
Related Reads
- Hawaii destination hub
- Humpback whales in Maui
- Haleakala volcano crater hike
- Sea turtles and cliff jumping at Ka’anapali
- Road to Hana
FAQ
Which island is better for families — Oahu or Maui?
Maui, in our experience. Oahu has more infrastructure but also far more crowds. Maui’s mix of hiking, beaches, and wildlife felt much better suited to travelling with kids.
When is the best time to visit?
February–March for whale season on Maui. Shoulder months (May, September–October) for smaller crowds and lower prices.
Is Hawaii expensive with kids?
Yes — it is one of the more expensive parts of our whole trip. Accommodation and car rental are the big items. Cooking some meals and using AirBnB with kitchen access helps a lot.