Around the island in 4 days: a guide to Oahu

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Hi everyone!

One of the many perks of living where I live is that long lost friends have no problem with traveling long distances and many hours to come visit. It’s always fun catching up with people you haven’t seen in a while, and I get the added bonus of getting to play tourist on this gorgeous island. There are still so many places I haven’t seen, so many hikes that I haven’t embarked on, so many restaurants with delicious treats that I haven’t yet tasted…so when my friend, Laura, decided to book a last minute trip to visit, it was the perfect excuse to plan a few adventures.

If you’ve ever been to Oahu, odds are that you know there are four sides. No, not the traditional north, east, south, and west, but rather northshore, windward side, town, and leeward side. While each side is beautiful, they all have distinct differences and quirks. I’ve compiled a short list of things to do in each region, perfect for a short 4 day trip.


  • Pick up an açaí bowl from Haleiwa Bowls. You get to pick all your own toppings. Yum!
  • Hit at least 2-3 beaches. My favorite is Waimea Bay.
  • Eat lunch at a food truck. Historic Haleiwa town boasts a few of the best. Giovanni’s garlic shrimp is my #1 favorite thing to order after a day in the sun. Don’t forget to pick up a fresh coconut to go with it at one of the fruit stands!
  • Poke around in some of the adorable boutiques. The most random little shops are sometimes home to the best treasures.

Windward side:

  • Take a hike to a waterfall, such as Maunawili Falls. This is the rainy side of the island so it’s always lush and green.
  • Enjoy lunch at my favorite place to eat on the whole island, ‘Ai love Nalo, which is on the windward side of the island in Waimanalo. The vegan restaurant supports local farmers and is so healthy and delicious!
  • Take a drive to Lanikai beach, one of the most picturesque places I’ve ever seen. It gets pretty crowded but the crystal clear aqua water is worth it.


  • It’s much noisier and more crowded than the other parts of the island, but it has it’s perks, such as a great assortment of restaurants, shops, and nightlife.
  • Do happy hour at one of the many restaurants or bars. Some favorites of mine include Doraku and Il Lupino, both in Waikiki.
  • Watch sunset from SKY Waikiki, Waikiki’s newest chic rooftop bar and lounge. And drink a Kailua Cobbler while you’re there.
  • Shop at Ala Moana Center, the largest mall in Hawaii and, in my opinion, one of the most beautiful malls ever. It’s conveniently situated between Waikiki beach and downtown Honolulu.

Leeward side:

(Unfortunately, Laura and I didn’t make it out to this side, but there is always next time.)

  • Swim with dolphins at sunrise. This is still one of those things I’ve been wanting to do but haven’t yet gotten around to. But word has it, if you’re up early enough, swimming with pods of dolphins isn’t too far fetched!
  • Lounge on the beach for the day. Some of the most stunning and uncrowded beaches are over here and as it’s the desert-like part of the island, you’re more likely to get that killer tan you’ve been dreaming about.

*Note: I would like to encourage anyone planning a trip to Hawaii to spend some time educating themselves on the history of this island chain and its people. Be respectful of the culture and the land!


On me: Amuse Society bikini top and bottom. On Laura: Rip Curl bikini top and bottom.


On me: Amuse Society sweatshirt. On Laura: Amuse Society sweatshirt, similar here.

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