Maui is the Hawaiian island most families ask for by name, and it earns the reputation. Wide, calm beaches like Ka’anapali and Wailea make it easy to keep younger kids happy, while the famous Road to Hana gives older kids and adults a full day of waterfalls, black-sand beaches, and switchback views they won’t stop talking about.

Most family trips split time between a resort base in West or South Maui and at least one day dedicated to Haleakala National Park: the sunrise reservation books up fast, so it’s one of the first things Dave locks in when planning a Maui trip.

Dave’s tip: Renting a car for at least part of the trip is worth it here more than almost anywhere else in Hawaii: the Road to Hana simply isn’t the same on a bus tour.

As a Certified Hawaii Travel Specialist, this is one of the destinations Dave has trained specifically on, from resort selection to inter-island logistics if you’re combining Maui with Oahu or the Big Island.

Oahu is the easiest first-timer’s Hawaii: a real city (Honolulu) with an international airport, resort-lined Waikiki Beach, and enough history and culture packed into one island that a week rarely feels like enough.

Pearl Harbor is a must for most families and groups, and it’s worth booking timed-entry tickets well in advance. Beyond the historic sites, Oahu balances easy resort days at Waikiki with a completely different vibe up on the North Shore, where the surf culture and food trucks make for a great day trip.

Good for: multi-generational trips where grandparents want an easy resort and grandkids want adventure. Oahu can do both without switching islands.

Dave frequently books Oahu as a stand-alone family trip or as the first stop on a multi-island Hawaii itinerary.