Top 5 Adventures in Oahu, Hawaii

Lanikai Pillbox (also known as the Ka'iwa Ridge Trail)

We wanted to experience the sunrise on Oahu and chose the Lanikai Pillbox Trail because its known for its amazing views of the Mokulua "Mokes" Islands (seen in the picture above), Lanikai Beach, Kailua Bay, and beautiful residential areas. We were staying in Waikiki Beach and left the hotel around 4:00am to accomodate the 45-minute drive and ensure we had time to park and hike to the top before the 6:03am sunrise. The hike was short but very steep in some places with a few scrambles. The steepest sections have ropes to help you on your way up and down so make sure your hands are free. Use caution because it can be muddy and slippery after a rain. Some people were scared to climb the rocks but it was so worth it. It wasn't dangerous unless you took the wrong route. You want to get there early to get the best spot for sunrise!

Distance: about 1.6 miles roundtrip (out and back)

Where: The trailhead is located in a residential neighborhood on Kaelepulu Drive across from the Mid Pacific Country Club in Kailua, HI

Elevation: 613 feet

Time: 45 minutes 

Level of Difficulty: Intermediate

Price: Free

Permit Required: None

Parking: There is limited parking in the neighborhood and it is strictly enforced. If you can't find a spot on Kaelepulu Drive, additonal parking can be found on Alapapa Drive. Other options are to park at the Kailua Beach Boat Ramp (0.7 mile walk), Kailua Beach Parking Lot (0.9 mile walk)which is a 15-20 minute walk. If you don't want to worry about parking, a ride share service will save you time.

What to bring: Lots of water. Definitely a Flashlight (flashlight on your phone will work) as it is really dark before sunrise, especially walking/climbing up a steep rocky hill. You could bring snack to enjoy during sunrise or sunset! Dogs are allowed and required to be on a leash, but your dog better be fit and ready to climb. If you want to bring a full size camera, be sure you have a backpack for your gear as you want both hands free for the climb up and down! There is not much shade, so apply sunscreen before you go.

What should you wear: Definitely running shoes/hiking shoes (do not attempt in flip flops)! Clothes can be anything athletic. There are great picture opportunities all along the way. My friend, Margo, and I wore the outfits in the picture above and it was perfect for comfort and pictures.

Island Helicopter Tour

We would recommend taking a helicopter tour as one of your first activities when you arrive. It was a great way to see the majority of the island before we visited the locations in person. Many sites like Diamond Head, the USS Arizona Memorial at Pearl Harbor, Hanauma Bay, and Kaneohe Bay were all on our itinerary, but seeing them all from the air provides a completely different perspective! We also were able to see rainforests and waterfalls that can only be seen on a helicopter tour. The flight over Pearl Harbor and the USS Arizona taking the same flight path that the Japanese took was chilling. There are great views from every seat. There were 6 in our party so we had the helicopter to ourselves and we had amazing unobstructed views the whole time! The captain was very informative. The only negative is that the video recording equipment our flight didn't work so we weren't able to purchase the video footage.

Company: Blue Hawaiian Helicopters Oahu

Where: Honolulu Airport 

Package: Complete Island Oahu Tour

Time: 65 Minutes 

Price: Around $455 a person 

What to bring: Polarized sunglasses and anything to take pictures with, that's really all you need, they supply you with everything else. We all brought our iPhones and I also brought a separate camera.

What to wear: Wear something comfortable and closed toed shoes (required). Blue Hawaiian recommends dark colored clothing to minimize glares for photography. A few of us wore white and we didn't notice any negative effects. Anything from athletic leisure wear to cute tops and pants/shorts. They make you wear large headphones, so I recommend not wearing big earrings or high buns.

Snorkel with Sharks

This was one of my favorite things we did on this trip. I am terrified of sharks but this is one of the coolest experiences. We did a morning 7:00am private tour as the weather is best in the morning. I was terrified before we got in the water, but once we were in, it was magical! There were around 30 to 40 sharks around us and we even saw a tiger shark. There are divers in the water with you to ensure safety as well as a photographer to capture amazing shots so all you have to do is enjoy the experience! I highly recommend One Ocean Diving because they are highly focused on education and conservation and have a 100% safety record. Not only did we have the best time, but we learned so much and came away with a completely new perception of sharks. If you want to learn more before you go, they have a new online course available on their website.

Company: One Ocean Diving

Where: Haleiwa Harbor

Time: 2 Hours 

Price: $150 per person or a private charter for $1500. Optional photography package is $250

What to bring: They do not allow small cameras in water, but you can bring a GoPro if it is mounted on a dark colored pole. However, they do have photography packages, which is what we did and it was so worth it because you can just enjoy the experience. The picture above is what the photographer took of me on our dive. You also should bring water and a few snacks. If you are prone to sea sickness, you should take sea sickness medicine the night before as well as 2 hours before your tour. 

What to wear: Dark colored bathing suit. They supply you with watershirts, snorkels, and fins. They do make you take off some jewelry if you are wearing any.

Horseback Riding On the North Shore 

We went on a Private Sunshine Horseback ride down the North Shore. We rode from 1:00pm to 2:30pm. We all got our own horse and rode down the beach, we saw a baby seal and so many beautiful views. All of our horses were very well trained, it was a very safe and comfortable ride. 

Company: Hawaii Polo Trail Rides

Where: Waialua, Hawaii

Time: 90 Minutes 

Price: Group Rides from $128 per person and Private Rides from $158 per person

What to Bring: Definitely bring water, It gets pretty hot so you want to stay hydrated. 

What to wear: You need to wear closed toed shoes for this ride. I also highly recommend wearing pants, I wore some linen beach pants which were perfect. My mom and Margo both wore shorts but you could chafe. Also bring a pair of sunglasses and a hat if you want to stay covered. I wore my bathing suit top and everyone else just wore tank tops or t-shirts.

Kaneohe SandBar 

We first saw the Kaneohe Sandbar on our helicopter tour. It was one of the most beautiful views I have ever seen. We all wanted to go there as soon as we saw it and luckily we already had a day scheduled for this! We did a private boat charter from the Heeia Kea Pier at 10:15am. The boat took us to the Kaneohe sandbar which had the clearest water, abundance of sea life, and many activities. We went snorkeling, paddle boarded, and swam all day.  Best time to go is at low tide, so check the tides. Captain Bruce has kayaks, paddleboards, floats and more that you will be able to use. This was such a memorable day.

Company: Captain Bruce

Where: He'eia Kea Boat Harbor

Time: Around 6 hours 

Price: $160 per person or private boat for up to 6 people ranges from $1150 -$1340

What to Bring: Sunscreen, Cameras (waterproof is best), Anything you would bring to a beach day. They have snacks and drinks for you on the boat but you can also bring your own! They do not have alcohol on the boat but you BYOB (only cans). Bring snorkels and fins if you want to snorkel, as well as towels. 

What to Wear: You should definitely wear a swimsuit. There are a lot of photo opportunities so definitely wear one of your favorites. Coverups for when you get on and off the boat. Sun shirt if you need to protect your skin. Sunglasses, hats, flip flops.