Some of my random Oahu experiences.

1. Hike the Wiliwilinui Ridge Trail

Most guides will tell you to visit the very illegal Stairway to Heaven Hike. But I don’t want to ruin your vacation with a hefty fine or even jail time! The Wiliwilinui Trail is located in an affluent neighborhood 20 minutes from Waikiki. The trail may start easy, but it’s definitely a moderate hike once you reach halfway. As you climb the steep stairs that take you to the top of the ridge, you’ll realize it’s worth it when you see both the west and east coast of the island.

2. Spend a Night (or Two) at The Royal Hawaiian

One of the ritziest and most fantastic experiences on the island can be found at the famous Royal Hawaiian hotel. This 100 year-old property is in the heart of Waikiki and decorated from floor to ceiling in a pretty pink hues throughout the property. While the hotel might have been built over the burial ground of a Hawaiian king, don’t let the ghost stories keep you from the fabulous buffet, the gorgeous view from the Mailani Tower or a decadent experience at the Abhasa Spa.

3. Catch the Billabong Pipemasters Surf Competition or Surf on Your Own at the North Shore

The North Shore is considered to be one of the coolest and trendiest parts of the island. Naturally, it makes sense that the annual surf contest is held in this surfer’s paradise where the swells are huge and the number of kooks are low. Keep in mind that competition dates may change due to the weather. We were in Hawaii for the entire “planned” week of the competition, but it started on the last day of our trip due to the poor surf conditions.

4. Eat Tropical Cuisine at The Sunrise Shack

After you’ve started your morning in the North Shore with some great surfing and sunbathing, it’s time to grab a healthy treat at The Sunrise Shack. You can’t miss this tiny, yellow shack along the main road through the North Shore. The eatery provides healthy smoothies and super strong coffees, but don’t forget to treat yourself to their scrumptious papaya bowl!

5. Pay Tribute to Fallen, US Servicemen at the USS Arizona at Pearl Harbor

On December 7th 1941, a day that will live an infamy, the Japanese army led a surprise attack on the United States of America and bombed Pearl Harbor during World War II. USS Arizona, a battleship built for and by the United States Navy, was hit along with 7 other battleships, 4 of which had sunk. 2,403 died that day and the USS Arizona was left underwater as a sunken tomb for the Americans that died. Today, we pay tribute to these fallen heroes by visiting their memorial and never forgetting what happened on that tragic day.

6. Play in the Sunflower Fields in the North Shore

On the way to the North Shore lies a private farm in Waialua that’s home to many fields including cotton, rice, soybean and wheat. Their most famous attraction is the field of sunflowers. In order to educate visitors about their property and farming, the owners have allowed tourists and locals to come take pictures amongst the sunflowers free of charge. Keep in mind, the sunflower season in this part of the island is extremely short. Very late October to early December is primetime for catching these tall beauties, but always call ahead to make sure they’re in season. (We were there for the end of the season, but the flowers had already died by then.)

7. Take in the Panoramic Ocean View at Pillbox Trail

Want to look like a hardcore hiker, but don’t want to actually commit? Try the pillbox trail on the eastside of Oahu.  Not only will you see the crystal blue waters of Lanikai beach, but with proper framing, the picture gives the optical illusion that you’re a lot more bad ass than you really are. Just beware, when they say “easy hike,” it’s definitely not “Los Angeles easy.” Unlike me, you should wear hiking shoes and athletic attire so you don’t twist your ankle on the steep hill.

8. Taste the Best Pork You’ve Ever Had at Kono’s

Kono’s is a multiple award-winning, local restaurant specializing in slow-roasted pork dishes ranging from sliders to sandwiches to burritos (not to mention their delectable milkshakes). And like all of the reviews and awards suggest, their pulled pork sliders on a sweet Hawaiian roll was probably one of the best snacks I’ve ever eaten in my life. There are locations all over the island in Haleiwa, Kapahulu and Kailua so you have no excuse not to shove all of the delicious pork in your mouth.