First Timer’s Guide to Oahu


Until a few years ago, I’d never even wanted to visit Hawaii; I thought it was just a honeymoon/romantic vacation destination. When I got the opportunity to go to Oahu with my parents for a steal, I was in, but I wasn’t expecting it to join my top ten list or anything… I was wrong. Like, super wrong. I absolutely loved it. There is so much more to Hawaii than just honeymoons. The mountains are stunning, the temperature is a pleasant 80-ish year-round with little humidity, it has history, lush tropical plants, clear blue water… I could go on, but instead, I’ll give you a beginner’s intro and suggestions for your next visit, be it your first or your twenty-first trip.

Although all the Hawaii islands are amazing, Oahu is a great “starter” island. Oahu is home to 2/3rds of the population of Hawaii, the capital city of Honolulu, a historical WWII site, and some delicious shave ice. There’s good infrastructure and plenty to do both indoors and out.

How To Get to Oahu

  • Daniel K. Inouye International Airport is the main gateway to Hawaii. If you live on the west coast, you can sometimes get really good deals on direct flights to Honolulu from San Francisco or Los Angeles, but east coasters will have to transfer… While Delta and Hawaiian Airlines both run direct flights from New York City, most of us here in the southeast will fly through Dallas or Los Angeles.

Where To Stay

I’d be ok with a barely standing shack on the beach, but if you’re looking for a little more here are a few options at different price points:

Moana Surfrider, A Westin Resort & Spa

Photo: Starwood Hotels & Resorts

  • High-End: Moana Surfrider – Known as the “First Lady of Waikiki”, the Surfrider opened in March of 1901, the first hotel in Waikiki. It’s beautiful gray/white exterior looks like a building out of time. There are rockers on the porch and a 117-year-old Banyan tree in the courtyard. Its guests have included royalty, authors, and Olympians.  But it’s modern where it counts, with the Moana Lani Spa, five memorable restaurants, and Westin’s Heavenly Beds.
  • Middle-of-the-Road: Waikiki Beach Marriott Resort & Spa – Just steps away from Waikiki Beach and numerous restaurants. Visit the Royal Kaila Spa for some relaxation and rejuvenation. Sit on your balcony and gaze out at the Pacific Ocean and the beautiful mountains. Oh, and don’t forget to grab your daily Mai Tai drink, included in the resort fee!
  • Easy-On-The-Wallet: Ramada Plaza Waikiki – It’s a little bit off the beach, but still within easy walking distance. The Ramada does boast no resort fee, so that’s a little more money in your pocket (to spend on shave ice). There are fewer frills, but still nicely appointed rooms with a calming decor. Lots of dining is nearby and you can walk over to Ala Moana Center, a four-level shopping mall, in just 10 minutes.

Where To Eat

  • Giovanni’s Aloha Shrimp Truck – With a name like Giovanni, you know it’s authentic Hawaiian, right? Ok, maybe not. But, it’s delicious and it’s iconic. Giovanni’s has two locations, both on the North Shore. The white trucks are covered in signatures from visitors dating back to 1993 (at the Kahuku location) and 1997 (at the Haleiwa location). They’ve won numerous awards and been featured in fancy food magazines. But, really, they’re just good food. A dozen shrimp (I’ll take mine scampi style) and two scoops of white rice. Maika’i! And, if you or someone in your group isn’t a shrimp eater, there are several other tasty options nearby (I had some excellent Korean bar-b-que).
  • Tanaka of Tokyo – I’m a sucker for Japanese Hibachi. If I won the lotto, I’d hire a hibachi chef to cook all my meals. I haven’t won yet though, so I’ll just keep going places like Tanaka of Tokyo, in Waikiki. Located on the third floor of the Waikiki Shopping Plaza, but cooler if you enter from the street and take the elevator up. It’s your typical hibachi fare, but the quality of the food is amazing and the service, from both the chefs and the wait staff, is top-notch. Plus, they have cool toilets in the bathroom… Go, eat fried rice, and be merry.
  • Kono’s Restaurant – Another spot in Haleiwa, on the North Shore. This is the spot to go to for some real Hawaiian eats. Nothing fancy here, just good food. Their Kalua pulled pork gets raving reviews, as do their breakfast burritos and milkshakes (try the Mud Pie milkshake).

What To Do

  • Diamond Head – While I do believe you should try unique adventures on your vacations, I have nothing against “touristy” spots either. Diamond Head is sort of a cross between those two though. The Diamond Head trail was originally built by the US Army in 1908 and it’s now a part of Diamond Head National Park. Though a hike may sound strenuous, this one is really suitable for most ages and fitness abilities – but, do use caution and know your own limits. There are several lookouts on the way up where you can stop for a breather and an amazing view. To get to the very top, where the stunning 360-degree views are, you’ll have to climb a few (100-ish) stairs. It’s all worth it in the end though! Try a guided tour to get even more out of your hike.
  • Snorkeling at Kaiona Beach Park – Hanauma Bay and Shark’s Cove are some of the most popular snorkeling spots on all the Hawaiian islands, and for good reason. But, popular also means busy. If you’re looking to be a little greedy and get more reef to yourself, Kaiona Beach Park is only 10 minutes from Hanauma. It has a healthy reef, lots of turtles, and Rabbit Island in the background.

Cap, from Samoa, shows off his coconut picking skills at the Polynesian Cultural Center on Oahu.

  • Polynesian Cultural Center – The PCC opened in 1963 as a village with houses that represented different South Pacific cultures, helping to both preserve those cultures and to share them with visitors. In its current form, there are six “villages” on-site: Samoa, Fiji, Tahiti, Tonga, Aotearoa (New Zealand), and Hawaii. Each village has locals that will teach you a little about their home country. There’s also an Imax theater that shows “Hawaiian Journey,” an immersive cinematic experience that takes you through the history of Hawaii from its violent volcanic creation, to modern day. It’s definitely worth a visit.
  • Valor in the Pacific – Valor in the Pacific is home to the sunken USS Arizona. It’s a very touching and educational experience, going through the museums that lead up to the moments of and during the attack on Pearl Harbor and eventually taking a boat over to the monument that rests over the battleship. Try to go earlier in the morning, before the crowds arrive so that you don’t feel rushed or crowded out on the memorial


You didn’t think I was going to let you visit Hawaii without getting a shave ice, did you?? Hawaiian shave ice is similar to a snow cone, only the ice is much finer, more like snow. Sure you can get the typical American syrups like cherry and lemon… But, go for the Hawaiian toppings like mango, pineapple, and coconut and a scoop of ice cream or a drizzle of sweetened condensed milk.

And no, I didn’t misspell it. That’s right, SHAVE ice. No ‘D’. If the sign reads “shaved ice” run. Run away and find one of these joints:

  • Matsumoto Shave Ice – Located in Haleiwa, Matsumoto’s is, quite possibly, the best shave ice on the island.
  • Uncle Clay’s House of Pure Aloha – In the Aina Haina Shopping Center, you’ll find Uncle Clay’s. It’s is also perhaps the best shave ice on Oahu.
  • Waiola Shave Ice – Having never been to Waiola, I can’t say if it’s the best shave ice, but I’m not going to say it isn’t either… It is, however, the oldest – originally started in 1940. You can’t stick around that long and not be the best, can you?

There is so, so much more to Oahu that what I’ve shared with you here. You really have to visit to believe how amazing it is, both in its beauty and its rich history. I certainly wasn’t chomping at the bit to visit before I actually went. Now, I find myself evangelizing about Honolulu on a near-daily basis…

Are you interested in taking an adventure to the Hawaiian Islands? I’d love to help you plan it!

First Timer's Guide to Oahu

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