Aloha Oahu! An Adventurers Guide to Hawaii

Pack your swimmers and lets go to Hawaii!

My time spent living in Kailua was one of the best experiences of my life and for all the years since I have been haphazardly passing on my favorite hikes and adventures for friends via text and hand drawn maps but I have finally compiled them here to share! Please message for more clarification and be respectful to the land and people, especially now with COVID!

Hikes

Three Peaks/ Olomana trail:

A physical challenge the entire way, it is particularly technical towards the 2nd and 3rd peak. If you want to make the full trip bring more water than you think you need. Not a great option if you have a fear of heights. Located on the Windward side (Kailua.)

Ka’au Crater:

The first hike I did on the island and possibly my favorite; I revisited this trail many times while living in Hawaii. Climb a huge waterfall and get an unbelievable view of Waikiki? Sign me up. Do it as an out and back or walk the ridge for a full loop. Not for the amateur or solo hiker, tread caution when conquering this challenging trail. Located on the Leeward side (Waikiki.)

Stairway to Heaven:

Famously illegal but also awesome and not actually very challenging. If you want to do this I recommend hiring a guide take you in order to avoid any issues ( fines for getting caught can be MASSIVE.) While it isn’t particularly difficult it can be extremely dangerous in poor weather conditions- people die and that’s why it became illegal. Matt Kievlan is a MASTER of the stairs and has gone up 500+ times, check him out for more info on this and other Oahu adventures.

Maunawilli Falls:

Equal parts easy and muddy, with one VERY BIG caveat - CHECK THE STORM REPORTS! Realistically you should be cautious of flash floods on every Hawaii hike but this is the only one that has trapped me with a sudden onrush of water. It’s a short drive from the Kailua side.

Pink Pillboxes/ Pu’u o Hulu:

This hike is short and steep, more of a physical feat that an enjoyable stroll but the views on top are absolutely incredible and it is an amazing spot for sunset. The pillboxes are a reoccurring theme throughout Oahu as they were originally used for communications and lookout in WW2- no wonder they always have the best views! These are located on the West side of the island, farther away from where most people stay but you can make the most of your drive by combining multiple activities.

Lanikai Pillboxes:

An iconic view of sunrise is located 5 minutes outside Kailua.it isn’t hard or long and could easily add an amazing view to your routine workout.

Hamama Falls:

An easy hike with an epic waterfall payout! Check it out after some rain to really see the water cascading.

Koko Head

Oahu’s natural stair master, this climb is brutal and only made worse because little old ladies WILL pass you on their daily trail runs. Gorgeous views and easy location from Waikiki.

Other Adventures worth trying

One Ocean diving:

This shark conservation company is absolutely incredible! Sign up for a tour to swim with the shark's CAGE FREE! This is my favorite recommendation, it is a must-do activity up in NS.

Lanikai Mokes:

Rent a Kayak (Military can get them on the cheap at K-Bay MWR) and paddle out to those two triangle islands off the coast of Lanikai. There’s a beach, a jumping point and occasionally some sea life on the way!

Kaneohe Sandbar:

Use those Kayaks or rent a boat and go out to the Kaneohe sandbar, back in the days before covid there were weekly parties here but who knows now.

Makua Beach:

Located on the Westside, this beach is heavenly. I use to do overnight camping here and wake up to swim with spinner nosed dolphins. While you’re over here go to Ka’ena Point State Park or do the Pink pillbox hike to make most of your drive!

Makau’u Tide Pools:

You can hike the lighthouse trail and then climb down to the tide pools, it's a surreal location on the far Eastside.

Turtle Bay Resort:

From the movie Forgetting Sarah Marshall it is also home to a world class golf resort and a weekly free Luau. Stop for a visit on a drive up the Coast.

Waimea Bay

In the Winter Waimea Bay is home to some of the worlds most gnarly surf competitions but in Summer it is a great beach with easy cliff jumping. While you are out in this area bring your snorkel gear to Sharks cove and Turtle beach.

Where to eat

Fresh Catch: The best no frills poke ( Kaneohe)

Nalu Health Cafe: My favorite Acai bowls in the world (Kailua & Waikiki)

Kalapawai Market & Cafe: Sandwiches & to go food at the market, nice candlelit dinners at the cafe (Kailua) Crepes No Ka Oi: My favorite is the savory pulled pork Crepe! (Kailua)

Cinnamons: Hangover breakfast galore…Be aware of long waits. (Kailua)

Mai-Tai Bar: Check out Happy hour drinks & apps while enjoying live music on the patio at Ala Moana Mall (Waikiki)

Side Street Inn ( 1225 Hopaka street): Not the place for gimickey aloha vibes but this food is the reason so many Hawaiians are fat. Think family style fried chick, fried rice and do not miss the farmers salad!

Matsumoto Shave Ice: Shave ice in Hawaii just hits differently, grab one while enjoying the art galleries around Haleiwa. (North Shore)

Sunrise Shack: Super cute Instagram vibes, fruits and smoothie bowls! (North Shore) Haweiwa Bowls: Take your bowl and go to the beach. (North Shore)

Konos: PORK! Kalua pork omlettle is the only way to end a morning of diving. (North Shore)

The Edge Pool Bar & Rum Fire at Sheraton Resort: Live music and great views (Waikiki)

Sunrise Pool Bar at The Modern: Super chic with a great mellow ambiance, located at the end of Waikiki Beach so there are fewer tourists. A great start to a Waikiki Beach bar crawl!

Dukes on Waikiki Beach: There’s no going wrong with Dukes, the food is good and it turns into a party with live music every Sunday evening (pre COVID) at Monkeypod Kitchen at Ko Olina

Monkeypod Kitchen at Ko Olina: located near the Four Seasons and Disney resort, go here specifically for their famous Mai Tai with lilikoi foam. The whole menu is good too.

North Shore food trucks: Giovanni’s Shrimp Truck is the most famous but there are plenty of great options to choose from.

Leonard’s Bakery: Home to the best homemade malasadas , fresh every day.