Planning the perfect family trip to Oahu starts with choosing the best time to visit. Hawaii’s tropical beauty shines year-round, but some seasons are better suited for family travel based on weather, costs, and crowds.

For families with school-aged kids, spring break (March-April) and summer (June-August) are ideal. During these months, you’ll experience warm weather and calm ocean conditions perfect for swimming, snorkeling, and paddle boarding. Many family-friendly activities, like luaus and outdoor movie nights, are in full swing during these peak seasons. However, these periods are also the busiest and most expensive. Hotels and flights tend to book up quickly, so planning several months in advance is key.

If you’re looking for a more budget-friendly option, consider visiting during the shoulder seasons—late April to early June or September to October. These months still offer excellent weather but with fewer tourists, making it easier to enjoy popular attractions like Hanauma Bay or Diamond Head without long waits. Accommodations and flights are often more affordable during this time, which can make a significant difference for families traveling on a budget.

Winter (November-February) offers a unique experience, especially if your family enjoys surf culture. The North Shore’s waves come alive during these months, attracting professional surfers from around the world. Even as spectators, your kids will be mesmerized by the awe-inspiring sight of surfers tackling massive waves.

If you’re planning to visit over a major holiday, like Thanksgiving or Christmas, book your flights and accommodations six to nine months in advance. Holiday seasons are incredibly popular in Oahu, with families flocking to enjoy tropical celebrations, parades, and seasonal luaus. While the vibe is festive, the crowds can be overwhelming if you don’t plan ahead.

My family flew in on Thanksgiving day and left a week later. It was a busy time, but that's to be expected in Honolulu/Waikiki most times anyway, so it wasn't bad at all for us.

We had a great time just being with each other.

Pro Tip: Check Oahu’s local event calendar before booking. Festivals like the Honolulu Festival in March or the Aloha Festivals in September add a cultural touch to your trip and are often kid-friendly.

Here are a few shots from 2024's Aloha Festival at Kualoa Ranch (the place where Jurassic Park was filmed!!!)

What’s your favorite time of year for a family vacation, and why?