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A Guide to a Jam-Packed Trip to Oahu, Hawaii

Someday, I will sink my toes into that Hawaiian sand, grab a shave ice and soak up the beautiful greenery in the most breathtaking U.S. state. It’s been a dream to journey to such a magical place, so I’ve done extensive research about my future trip there. I’ve almost never heard a bad thing about any of Hawaii’s islands, but the stand-out star definitely seems to be Oahu.

Obviously, the city of Honolulu is where many people roam when they land on the islands, but the true spirit of Hawaii can be found outside of city limits in Oahu. With year-round beautiful weather, prime swimming conditions and tons of naturally grown goodies, what wouldn’t you love about a place like this?

It’s also a cultural melting pot that draws influence near and far from a myriad of traditions. From American and European settlers to recent Pacific island arrivals and Asian immigrants, it’s fascinating to watch the island evolve and find ways to incorporate all these wonderful cultures. This rings true through annual festivals, food, dance and folklore shared and passed down by generations.

Through advice, research and a lot of daydreaming, here’s my plan for a future trip to Oahu, hopefully sooner rather than later.

How to Get Around the Island

As a huge fan of road trips (obviously), I would love nothing more than grabbing a car and hitting the road with my best pals. Beyond Honolulu and the famous Waikiki strip there are beautiful, wild routes to explore and discover hidden spots for relaxation.

The road to Hana is the most iconic and a great place to start. It’s a slow-paced route past stunning scenery and plenty of opportunity to stop for fresh fruit from farm stands. On the north shore, the road to Kauai is well worth the excursion too, especially for some beach time at Hanalei Bay, one of the prettiest spots to soak up the sun in the world. Explore various driving adventures, as some are optimal at sunrise, while other require a strong stomach and nerves of steel. Just wear your seat belt and hold on!

Where to Stay in Oahu

Obviously, if I’m going to go all the way to Hawaii, I’m certainly going to splurge on Oahu vacation rentals – the closer to the water the better! Each region of Oahu has something a little different to offer, so do your research about what will work best for your group.

If you hope to swim and hang out for your trip, a property in the North Shore can be ideal, especially with a private pool. Closer to the city of Honolulu is another option for those who like urban activities but want an alternative to some of the larger resorts. Anywhere you’ll be able to try a surf lesson or two.

Having a holiday home is the best option for Oahu, as it allows lot of freedom and space for your group to indulge. Not to mention, you can be free of any all-inclusive resorts and truly tuck into the great food and fun that is off resort. The island offers tons of these in beautiful, easily accessible locations, with full equipped kitchens, giant bedrooms and views that are unforgettable. We’re big fans of reserving a home together so we can all be under the same roof on holiday.

What to Eat in Hawaii

I’ve heard eating in Hawaii is always an adventure. Food is wonderfully fresh…except for the Spam!  So speaking of spam, let’s talk breakfast. This delicious canned meat mystery is best with eggs in the morning or wrapped up with rice and seaweed paper as a sushi.

And if you rather just eat Spam any time of day, be in Oahu in April to take part in the annual Spam Jam. Waikiki shuts down a whole avenue to accommodate thousands of spam fans noshing on street food all afternoon. There’s countless food stands, live entertainment and more. It’s well worth the trip.

What needs to happen during a road trip is stopping for a plate lunch. This is the perfect way to get used to how Hawaiians grub. It’s a heaping portion of two scoops of rice, a scoop of macaroni salad and a meat choice enjoyed anytime of day. Choose some favorites, such as barbecued pork, chicken katsu (chicken in fried breadcrumbs) or beef teriyaki. The best diners and road stops that have these are open 24-hours. It’s a satisfying and wallet-friendly way to five right into some great grub on the island of Oahu.

Really all this food is just leading up to the grand finale – amazing sweet treats in Oahu take the cake. Is is awful to say I would love to see those Hawaiian beaches, but really I just want a huge cone of shave ice?! That’s definitely why I’d deal with a long plane ride to paradise.

Shave ice is a Oahu mainstay. Piles of finely haved ice is formed into a cone and topped with various sugary flavors. Choose from pineapple, lychee, mango or even green tea. The best part though are the sweet azuki beans in the bottom of the paper cone and the ice cream on top. Go big or go home right? Besides shave ice, malasadas are very popular and look like filled donuts dusted with sugar.

Have you been to Hawaii before? What about the islands do you love? What is your favorite island?

Eileen Cotter Wright

Author Eileen Cotter Wright

Eileen Cotter is a freelance travel writer, social media manager and owner of Pure Wander. She's been to more countries than your kindergartner can count, and she's our resident expat extraordinaire. Follow her on Twitter @Crooked_Flight

More posts by Eileen Cotter Wright

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