The Ultimate Travel Guide to Oahu, Hawaii

Getting paid to live in Hawaii sounds like a distant dream, but for Caitlyn Swope, it’s the real deal. After hearing about how one of her sorority sisters worked as a counselor at the YMCA Camp Erdman, Caitlyn was hooked. An application, video interview and three recommendations later, she was on a plane to Oahu to be a photographer at this camp in Wailua for the summer. (The show Lost was filmed on these very campgrounds.) The paycheck for taking and editing photos of campers isn’t hefty, but room and board is free — in an air-conditioned hut on the beach no less.

I asked Caitlyn all about living in Hawaii, and she dished all the deets from must-see Oahu spots and what to pack:

If I’m traveling to Oahu, what should I do?

1. Kailua Beach 

It’s the best beach on the island in my opinion. The water is really calm, clear, and shallow, and the sand looks and feels like flour! It’s also in a great location: close to local shops and restaurants. After you’ve spent the day lounging at the beach, head on over to the Lanikai Pillbox hike. It’s super close, and the top has great views of the mountains and two small islands in the ocean.

2. Diamond Head Hike 

It’s on a lot of travel websites and for a good reason. It only takes about an hour total and it’s not super difficult, but the view is incredible: panoramic views of the crater, the ocean, and all of downtown Honolulu. 

3. Duke’s in Waikiki

Named after the famous surfer Duke Kahanamoku, it is popular for its lunch and dinner, but I actually went for their brunch buffet. It’s right on the water, and the food was delicious with plenty of variety. They are also famous for their “Hula” pie, which is made of a dark chocolate cookie crust, macadamia nut ice cream, rich fudge sauce, macadamia nuts and whipped cream. 

4. The Sunrise Shack 

It has two locations: the original, on the North Shore and a more modern facility in Waikiki. They are very well known for their colorful and nutritious smoothie bowls. I recommend the Blue Dream Bowl or the Tropical Smoothie; both make for a light breakfast or a great afternoon snack. 

5. Haleiwa (pronounced “Holly-E-Va”)

It’s a cute little surfing town on the North Shore. My friends and I go there just about every Friday night because it’s close to the camp I work at. They have lots of food trucks, but their most famous is Giovanni’s Shrimp Truck. They have cute shops with Hawaiian-inspired art prints, unique t-shirts and non-tacky souvenirs. 

6. Snorkeling at Shark’s Cove by Waimea Bay

Don’t worry, there’s no sharks here! It’s named that because the pools look like a shark bite from above. There are an abundance of colorful and tropical fish in the clear water. Plus, it really shallow, so you don’t have to be a strong swimmer to enjoy the experience. Right across the street are a variety of food trucks and places to buy or rent goggles and snorkels if you didn’t bring them. 

If I’m traveling to Hawaii, what are three items I have to pack?

Comfortable and waterproof shoes. I do lots of hiking here, and the ground is often muddy or rocky, so I recommend Chacos or something similar. 

An insulated water bottle. It is hot and humid here. You’re going to want an ice cold bottle of water on you at all times. 

An adventures spirit! So cheesy, I know, but you have to be flexible, willing and bold to make the most out of your time on the island. Wake up an hour earlier to do that hike, and don’t be afraid to jump off the cliff into the refreshing turquoise water. You’ve come all this way, so do everything you can and don’t hold back. There are so many epic places to explore on this island that it’d be a shame if you spent all day at your hotel pool.

How do you afford to live there?

To be completely honest, you don’t. To put it in perspective, a bottle of kombucha back home is usually around $2.75, and I haven’t been able to find one for less than $5.50 here. I really lucked out with free room and board. If you want to move to Hawaii, you will have to make some sacrifices. An average-sized house is usually around $700,000 here.

If you really want to live in Hawaii, but the prices are totally out of your budget, it is technically legal to camp anywhere on the island. Many locals pitch tents on the beach on the weekend.  Another option that I have heard that people do here is stay with a host family through WorkAway. You can move in with people all over the world for free in exchange for doing various tasks like babysitting, cooking, cleaning and yard work. If you have a desire to live here, you can absolutely do it, you just have to be creative and look around.

Any other pro tips for traveling to Hawaii?

If you make it all the way to Oahu, it’s an affordable and quick flight to any of the other Hawaiian islands. I suggest hopping over to see another one since they’re so close together. I flew to Maui over the 4th of July weekend. I visited the Iao Valley, a black sand beach, and drove the Road to Hana. Some of my friends went to Kauai and saw the epic Waimea Canyon there, which is known as the Grand Canyon of the Pacific. Any island you choose will be a good choice! They are each unique with endless opportunities. 

All photos courtesy of Caitlyn Swope.

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