The best hikes, beaches, and eats on the East Shore Oahu

Oahu may be known as the busiest and most touristy Hawaiian island, but head over to the East Shore of Oahu and you’ll discover stunning hikes, picturesque beaches, delicious local food, and serenity.

Crouching Lion Mini Hike

This was one of my personal highlights from the entire Oahu trip. Enter this address into your GPS: 52-180-52-204 Kamehameha Hwy and park on a small rugged parking strip on the right side of the road (as you’re heading North). Walk south down the highway and there will be a warning sign between the ‘do not pass’ sign and the telephone poll behind it. Walk through the clearing and the trampled path should be obvious, especially on a dry day; it leads up the hill and there is a fallen tree on the left you will need to climb through. From there hike straight up the side of the ridge; beware of loose rocks. Chew made a half-joke that Hawaiians don’t believe in switchbacks, so be prepared to get your heartrate racing. When you finally reach a flat spot and feel the ocean breeze, be sure to turn LEFT towards the crouching lion (right will lead you along the ridge trail which is rated very difficult and dangerous. Don’t attempt without thorough research and preparation). You’ll need to shimmy under a massive boulder and climb up one last time to reach the top of the lion. You’ll be rewarded with sweeping views of the Kahana Beach, the neighbourhood below, and the refreshing ocean breeze. Going down is more difficult than going up, especially for those that don’t love heights (i.e. myself). Just take your time, test your footing, and stay low to the ground so if you do slip, your butt will hit the ground first. The entire hike will take anywhere from 1 to 1.5 hours, depending on how long you spend at the top taking photos and soaking in the view. Also learn from my mistake and do not wear white bottoms. They will definitely get dirty.

BONUS: If you walk on the side of the road opposite to the trailhead, towards the parking area, you’ll spot a tire swing by the ocean side. We trekked over to give it a try. It’s a beautiful lookout spot too.

Lanikai Pillbox Hike

We did this hike right after Crouching Lion so we did it in the midday sun while running low on water. Not a good combo. Some people have suggested doing a sunrise hike here, and that would certainly be less hot; just be careful navigating the trail in the dark. Parking for this hike is a tad bit more difficult than Crouching Lion as you will need to find parking in the residential area. General rule of thumb is to stay at least 4 feet away from peoples’ driveways and of course read the signs. We went on weekend so locals were out too, making it busier than normal. Like the Crouching Lion, the initial ascend is steep (no switchbacks) so use the same precautions I mentioned above. After gaining sufficient elevation, the last stretch to the 1st pillbox and the path between the 1st and 2nd pillbox are easy peasy. The 2nd pillbox is less crowded so I think it’s worth the extra few steps. Allow time to cool off in the very strong ocean breeze (or wind…) and enjoy the view of the two little islands (the Mokes as the locals call them) sticking out of the beautiful blue ocean. If you do choose to do this 1 hour hike in the scorching sun, wear lots of sunscreen and stay hydrated. This is where I burnt the tops of my shoulders. Don’t say you weren’t warned.

Lanikai Beach

After working up a sweat hiking to the pillboxes, a dip in the ocean at Lanikai Beach is exactly what we needed. It’s a calm white sand beach that’s perfect for chilling at and frolicking in the turquoise waters. I initially read that it’s a beach good for snorkeling but we did not come across any coral reef or fish. Nevertheless, it was a great beach for relaxing at. No natural shade though, so bring a beach umbrella! Parking situation is exactly the same as Lanikai Pillbox; pair the hike with a trip to the beach so you don’t need to move the car.

Kailua Beach Park

I like Kailua Beach better than Lanikai because there is more parking, freshwater shower facilities, bathrooms, and the same beautiful soft white sand and blue waters. I would still suggest avoiding weekends here because it’s packed! Great beach for relaxing at.

Waimanalo Beach

Like secluded beaches? Find your own strip of sand along this 5 mile long beach on the east shore of Oahu. While we were there, there was a family getting a photoshoot done. This quiet beach makes it a great spot for photos with minimal distractions in the background. There is an ‘official’ beach park entrance but if you park in the residential neighbourhood around Ehukai cross Laumilo street there are beach entrances there too (no facilities). It’s a really quiet beach (especially on weekdays) with some waves during the summer months, big enough for newbie boogie boarders to try and catch a wave or two. I managed to catch one wave to shore and it was exhilarating. #truenewbie The rain started to come down quite heavily when we were there so we had to pack up and move to Kailua Beach. When it rains it can get a bit chilly so just check the local weather forecast (i.e. the exact area, not just ‘Honolulu’ because weather in Hawaii can vary with just a 5 minute drive) if you want to avoid unpleasant weather.

Lanikai Juice

See our review of their Honolulu location.

Kailua Sunday Farmers’ Market

We dropped by not too long before their closing time so booths were no longer fully stocked and some were even starting to pack up. Nevertheless, we got some fresh coconut water and some delightful kombucha. At the fresh coconut station, you can also purchase natural bamboo straws; very cool souvenir! The kombucha was $6 for 16 ounces, which is a decent price. Although they were sold out, I was told their mango flavour was their most popular one. This market is fairly small and only worth going to if you’re passing by. If you’re in Kailua looking for a big farmers’ market, go to the Thursday evening one.

Ai Love Nalo

This cute vegan café is very close to Waimanalo (‘nalo’ for short; ‘I love nalo’, get it?) Beach. We got their Poi Perfect Parfait and Oh Wow Lau Lau plate to go. Poi is taro puree and the lau lau plate is a sampling of veganized traditional Hawaiian dishes. Lau lau is usually pork wrapped in edible lu’au leaf, but this version had hearty local vegetables that tasted like potato and carrots. There was a side of tofu poke (you can choose spicy or non-spicy), a light salad, and your choice of brown rice, millet or half and half. Turns out half and half is literally half a scoop of each, and not a mix. Just FYI. It took a while for the Lau Lau to come out but everything was very delicious and healthy. The café interior is cute and cozy, and people of all stages of life were eating there on a weekday. We wished we had more time to return to Ai Love Nalo to try more of their dishes, especially their soft serve sundae (that chocolate shell though…) A definite must-try for our fellow veg-heads.