Oahu, Hawaii

Known for: Waikiki Beach, Pearl Harbor, North Shore surf culture

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.