Sooo you’re ready to finally go on a lil ADVENTURE and you chose Oahu! I’m so so excited for you and I want you to have the BEST time here. Planning a trip can be somewhat overwhelming, am I right?? especially a place like Oahu, where everything sounds like a good idea. so hopefully I can make it easier for you, friend!
If you didn’t know, I moved to the island of Oahu in May of 2019, taking a break from my solo traveling abroad. it was time for me to “settle down” (a little bit) and get some consistency in my life.
I landed, grabbed the keys to a very overpriced Jeep rental (like a total basic B) and headed straight for my first hike. didn’t miss a beat.
I quickly fell in love with this little island, even more so during the pandemic. the landscape absolutely takes your breath away. I mean, what’s not to love? anyway. here are the top 6 hikes I’d recommend if you’re planning a trip to Oahu!
Located on the east side of Oahu, Lanikai Pillboxes is a short hike but provides legit screensaver-worthy views.
The 1.8 mile roundtrip trail starts with a steep vertical incline, then hits relatively flat terrain followed by a hilly peak before reaching the summit marked by two “pillboxes” (former military bunkers). Because the entrance to this hike is buried within a residential neighborhood across from the Mid Pacific Country Club, parking can be tricky, so adhere to the no-parking signs and be respectful of homeowners’ driveways. The Pillboxes put you in a prime location for venturing into Kailua Town for post-hike light bites at the Kalapawai Café (be sure to order the browned-butter salted chocolate chip cookie for later), followed by shave ice, a Hawaiian staple, at President Obama’s favorite haunt, Island Snow.
One of the more strenuous island hikes, is a former railway turned hike that is not for the faint of heart. Comprised of over 1,000 railway ties arranged like stairs, this 1.5-mile roundtrip trek will test the endurance of even the most avid hikers with steep inclines and a portion that acts as a bridge, as the under footing has completely eroded.
The panoramic views of Hanauma Bay, Hawaii Kai, and Makapu’u make this hike worth it. Try to get here before it gets too hot, and be sure to pack plenty of water. When finished, head into Kaimuki, a suburb of Honolulu, for brunch at Koko Head Cafe.
4. Makapu’u Lighthouse Trail
5. Three Peaks/Olomana Trail
6. Crouching Lion Hike