Right away, my research showed it would be pricey. I ruled out my first island choice, Maui, and decided on Oahu as it was more affordable.
I’ve spent time on Maui before and love it for the variety of activities and ample natural beauty.
I thought Maui would be more remote-feeling than built-up Oahu but more family-friendly with a young child than Kauai or the Big Island, known for great hiking that we knew we wouldn’t do with a young, fidgety child.
I found cheap flight deals to Maui from Los Angeles but was shocked by my hotel search results. I wanted to stay in a nice hotel with child-friendly pools and food and drink service as opposed to a condo or Airbnb where we’d have to make our own meals.
I was a parent who wanted to be on vacation, after all.
But a standard room in a four-star hotel cost nearly $1,000 per night when I searched on Google a few months in advance. Even smaller hotels with fewer amenities commanded $700 per night.
On Oahu, in Honolulu, on the other hand, I found standard hotel rooms for around $250 to $300 per night on Google.
Hilton Hawaiian Village Waikiki Beach Resort, which had all the amenities I wanted, starts at $279 for a standard room, depending on the time of year, a representative for the hotel told Insider.
I could book a one-bedroom suite there for the same price as a standard room on Maui.
Not wanting to spend all our time in Honolulu, we decided to start at the Hilton for three nights, followed by a two-night splurge at Aulani, a Disney Resort & Spa in Ko Olina, before wrapping up at The Royal Hawaiian back in Honolulu on Waikiki Beach for two nights, which I booked with credit card points.
Seven nights at four-star hotels would not have been possible for us on Maui, and all three were in places we had never been.