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Hawaii: Two Weeks in Paradise… With My Mother-in-Law

How does spending a week in Hawaii sound?

Fantastic, right?

How about spending two weeks in Hawaii? Still amazing? Now, what if I told you your mother-in-law was coming with you?

Before you start sending me sympathy cards, let me say this: I actually get along really well with my mother-in-law. No, seriously. We laugh at the same jokes, travel well together, and she’s always up for an adventure (or a solid nap on the beach). So when the chance came to spend four days on Oʻahu and ten days on the Big Island, we didn’t hesitate. Hawaii had always been high on our list, and we were determined to pack in as much as humanly possible.

Spoiler alert: we did pack it in. So much so, in fact, that I can’t possibly fit it all into one post. This is just the warm-up round—a taste of the magic before I dive into the nitty-gritty in the next two features.

A Few General Impressions from Hawaii

One of the first things that caught my attention was the sea of Jeeps cruising down every road. As someone who loves Jeeps, it felt like I’d stumbled into my own personal utopia. With the tops off and the breeze in our hair, it didn’t take long to slip into full island mode.

On a particularly hot afternoon, we made our pilgrimage to Matsumoto Shave Ice, and let me tell you—this was no ordinary snow cone. The texture, the flavor combinations, the sheer joy of it all… I genuinely felt like I had been missing out on something extraordinary my whole life.

We followed that sugar high with a stop for malasadas, and if you’ve never had one of these warm, sugar-coated, custard-filled pastries, put it on your list immediately. They’re ridiculously good. Diets don’t count in Hawaii, right?

Getting around both islands was refreshingly simple. The roads were easy to navigate, and even a cross-island trip rarely took more than a couple of hours. We loved the flexibility of being able to plan a spontaneous beach stop or a scenic lookout detour whenever we felt like it.

And speaking of beaches, I’ve never seen such a concentration of high-quality beachwear stores in my life. Every corner seemed to offer another boutique packed with stylish swimwear, breezy dresses, and all the accessories you never knew you needed until you saw them. Hawaii isn’t just paradise for nature lovers—it’s a haven for beach fashion, too.

What’s Next?

In the next post, I’ll take you with us through Oʻahu, where we stayed just off Waikīkī Beach in Honolulu. From watching the sun rise over Lanikai to getting blasted by red-flag waves at Sunset Beach Park, every day was something new. We hiked, ate, learned, and even paid our respects at Pearl Harbor.

And then?

We flew to Hawaiʻi (the Big Island)—a completely different vibe. Think lava tubes, green sand, whales breaching, and swimming with manta rays in the moonlight. We stayed in Waikoloa Village, explored petroglyphs carved into lava fields, and drove to the summit of Mauna Kea.

Both islands offered so much, and each had its own personality. But together? It was the perfect trip.

Want More?

Stick around for the full breakdown of each island in my next two posts. But if you’re already dreaming of Hawaii, here are a few more things that didn’t make our itinerary, but might belong on yours:

  • Snorkeling at Hanauma Bay (Oʻahu) – One of the best snorkeling spots in the world.
  • Waipiʻo Valley (Big Island) – Epic views and taro fields.
  • Kona Coffee Farm Tours – If you’re a coffee snob, this is your moment.
  • Helicopter Tours over active volcanoes – Bucket list stuff.

Until then—aloha. 🌺

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