Family Hikes on Oʻahu’s Windward Side – A Local’s Guide to Easy & Adventurous Trails

TL;DR

Explore Oʻahu’s windward side with these family-friendly hikes ranging from easy strolls to adventurous climbs. From waterfalls to pillboxes and jungle trails, this local guide highlights the best trails for every age, plus what to pack, safety tips, and where to eat after your hike.

Oahu Family Hikes for all Adventure Levels

If you’re on the hunt for Oahu family hikes, I’ve got your back. I’ve taken (ahem, dragged) my kids on hikes since they were babies so let’s dive in and explore some options on the windward side of the island. If you’re staying in Waikiki and want to stay close, this post lists family hikes on that side of the island.

Below I have family favorite hikes unofficially ranked from most adventurous – with a rating of “5” – to least adventurous with a rating of “1” (one being more of a stroll than a hike). Pick and adventure level and let’s go!

Crouching Lion Trail, Ka’a’awa: Level 5

Crouching Lion is a short but intense, slippery scramble to an outcropping with coastal and valley views. Big drop offs make it a hike best suited for older kids (who are comfortable with heights).

Lanikai pillbox trail – The one hike to rule them all: Level 3

The Lanikai Pillbox Trail is a quick scramble up the hills above Lanikai and Kailua, and the payoff? Unbelievable views of the bluest ocean crashing around a smattering of rocky islets. My family and I have been hitting this neighborhood trail since our kids were still in diapers. This is one of the most popular Oahu family hikes (for good reason) and it tends to get crowded, but evenings are lovely if you want to avoid crowds.

Maunawili Falls trail, Waimanalo: Level 3

As of 2023, access to the popular Maunawili Falls trail is temporarily closed from the Maunawili neighborhood. However, you can still access it from the Maunawili Trail (another amazing trail worth checking out) from the Pali Road parking lot. It will be a longer hike, but much less crowded.

Makapuu lighthouse + tidepools, Makapuu: Level 2-3

The hike to Maapuu lighthouse is an entirely paved (stroller friendly!), uphill ascent that rewards with you views of the windward coast (and whales during the winter!). There’s a trickier side trail from the whale viewing areas that drops steeply down the sharp, lava coast to tidepools below. When the seas are calm, you can explore the flats and float in the oversized tidepools. More often than not, the surf is rough on this coast so stay back and observe before trying the pools and avoid them during rough weather.

Hamama Falls Hike: Level 2

Hamama Falls is a hidden, uncrowded gem of a trail on windward Oahu. The hike takes you through lush, almost jungle-like forest, and it’s like something out of a movie. It ends in a modest waterfall that feels like a little secret paradise.

Likeke Falls Trail, Kaneohe: Level 2

The Likeke Falls trail is another favorite in the list of Oahu family hikes. When the kids were little, this was a regular family hike because its so short and the falls are fun to play in. Access to the trailhead is through a private parking lot and over the years, there have been changes. The current owners of Ko’olau Ballrooms charge a $10 parking fee and the gate is open from 8am-4pm. Avoid parking along the narrow road outside of the gates which are prone to car break-ins. Sigh. I say this from personal experience.

Kawainui Marsh trail, Kailua: Level 1

Kawainui marsh trail is popular with residents who you will find walking, jogging, or biking along the scenic route. If you’re staying in Kailua it’s worth a visit for a morning or evening stroll. You can even find some native waterbirds foraging in the marsh. Avoid during the middle of the day when its just too hot.

Preparing for your Hawaii family hike

Preparing for Oahu family hikes requires a bit of planning to ensure everyone’s safety and enjoyment. Here are some steps to help you prepare.

Pack essential hiking supplies

• Reef-safe Sunscreen. Many of Hawaii’s hikes are along exposed ridge trails.
• Rain protection. Rain can surprise you on the sunniest day. I bring a lightweight drybag to keep valuables and camera gear safe. A long-sleeved shirt and quick-dry clothing is usually enough to keep you comfortable if you get caught in a rainstorm, but layers or a light rain jacket will help in the winter and/or on long hikes.
• Shoes with grip. You can leave the clunky hiking boots behind. Most important for slippery Hawaiian trails is shoes with flexibility and grip.
• Alltrails.com. An excellent hiking app to help you navigate and prepare. You can also learn about current trail conditions and any closures, permits, or fees.
• Geocaching app. Speaking from personal experience, kids can get whiny on hikes. Our fail-proof anti-whine strategy is to hike with friends or, when that’s not possible, search for geocaches along the hike. Don’t forget to brink some trinkets to swap out.
• Water and snacks. Even short hikes can take longer than anticipated. Bring more water than you think you will need.
• Basic First aid kit. You can pick one up at Target or Long’s if you forgot yours
• Wipes and diapers. I remember all too well the time my toddler had a major diaper blowout midway through a 3-mile out and back hike and I forgot to pack diapers. Or wipes. Or a change of clothes.

Can you swim in Hawaii’s freshwater pools?

If you stumble along a fresh water pool, waterfall, or stream in Hawaii, you will usually find a group of kids or adults playing in the cool water. However, it’s not without risk. Leptospirosis is a bacterial disease present in freshwater puddles, ponds and streams. It’s passed through open cuts or through soft tissues (nose, eyes, mouth). Decide where your comfort levels is, but don’t go in with open cuts, avoid putting your head under water and definitely don’t drink the water.

After your Oahu hike – Family activities on the windward side

If you’re looking for some fun after your Oahu family hikes, you don’t have to travel far. There are many family friendly activities on the windward side.

Local Eateries

Fill your post-hike bellies with tasty local eats and then head back out for more.

• Waiahole Poi Factory. True Hawaiian food that you must experience. Excellent after a big hike and don’t skip dessert!
• Kahuku Superette. This unassuming convenience store serves up some of the tastiest poke on the island. Grab some poke bowels and head to the nearest beach for an instant picnic.
• Over Easy. One breakfast options for the early risers. Local, fresh and super tasty!
• Kalapawai Market. A friendly place to grab anything from a morning cup of coffee, a delicious deli sandwich or pizza to an award-winning full-service dinner.

Favorite family beaches on the windward side

The windward side of the island has many protected bays making ocean conditions calmer and more family-friendly. Try out some favorites below –

• Lanikai Beach. I’m a firm believer that a great day starts with a sunrise hike to the Lanikai pillboxes followed by a swim in the cool blue on Lanikai Beach below and then Over Easy for a well-deserved brunch.
• Kahana Bay Beach. A rustic, mellow beach with ample shade and few people.
• Kaiona Beach. Something a little different. Sea walls and shallow water make for perfect baby and toddler pools. A great spot to splash in the shallows or float and relax.

5 Must do family activities in windward Oahu (that aren’t Oahu hikes or the beach)

1. Kualoa Ranch. Maybe the most majestic place on the entire island. We have done every tour as a family (ebikes are my absolute favorite tour followed by the ATV adventure) and jump at any chance we get to visit the ranch. This includes a very painful half marathon we slogged through a few years ago.
2. Hoomaluhia Botanical garden. Hoomaluhia Botanical Garden offers a unique blend of natural beauty, cultural experiences, recreational activities, and educational opportunities that make it a wonderful destination for anyone looking to immerse themselves in the beauty and diversity of Hawaii’s flora and fauna. AKA, there’s something for everyone. Even if it’s a quick drive to the end of the road and back.
3. Kaneohe Sandbar. Sort of a beach, but more like an island in the middle of Kaneohe Bay. The views are unparalleled and it’s a great spot to snorkel with turtles, eagle rays, and colorful fish. If you can find a way out there, it’s worth the effort!
4. Byodo-In temple. A beautiful temple tucked back against the sheer Koolau mountains. A peaceful place to wander and feed the giant koi fish.
5. Family photo session! Let me plan something fun for your family so you can take home great memories and beautiful images from your time in Hawaii. Contact me today to start planning!

Our Top Tips for Oahu family hikes

Prioritize choosing easy to moderate trails suitable for your group, pack essentials like water and sunscreen, start early to beat the heat and crowds, respect nature, and stay informed about trail conditions. Use extra caution around freshwater to avoid leptospirosis. Take breaks to enjoy the scenery and use your Oahu family hikes as an educational experience for your family.

FAQs

What are the best family hikes on Oʻahu’s windward side?
Favorites include Lanikai Pillbox Trail, Likeke Falls, Hamama Falls, Makapuʻu Lighthouse, Maunawili Falls (once it reopens), and the Kawainui Marsh trail for an easy stroll.

Which hike is best for adventurous families?
Crouching Lion in Kaʻaʻawa offers the biggest thrill — it’s short but steep with sweeping coastal views and a good dose of adrenaline.

Are there easy hikes on Oʻahu for kids or toddlers?
Yes! Kawainui Marsh Trail and the paved Makapuʻu Lighthouse Trail are stroller-friendly and perfect for little explorers.

Is it safe to swim in freshwater pools on Oʻahu hikes?
Swimming is common but comes with risks like leptospirosis (a bacterial infection found in streams and ponds). Avoid open cuts, keep your head above water, and skip it after heavy rains.

What should I pack for family hikes on Oʻahu?
Bring reef-safe sunscreen, lightweight rain gear, grippy shoes, plenty of water, snacks, wipes, and a small first aid kit. Don’t forget the geocaching app to keep kids engaged!

Are there any entrance fees for these hikes?
Most are free, though Likeke Falls charges a small parking fee ($10-$15 at Koʻolau Ballrooms). Always check for updated hours or parking restrictions before you go.

When is the best time to hike in Hawaiʻi?
Mornings are cooler and less crowded. Winter brings pleasant hiking weather, but pack rain protection for surprise showers.

Where can families eat after hiking on Oʻahu’s windward side?
Local favorites include Waiahole Poi Factory (Hawaiian comfort food), Kahuku Superette (poke bowls), Over Easy (breakfast in Kailua), and Kalapawai Market (coffee, pizza, or deli sandwiches).

What are fun things to do after hiking?
Cool off at Lanikai or Kaiona Beach, visit the Byodo-In Temple, explore the Kaneohe Sandbar, or take an e-bike or ATV tour at Kualoa Ranch.

Can I book a family photo session after our hike?
Yes! Little Bird Photography offers playful, natural photo sessions that capture your family’s Oʻahu adventure — from jungle trails to beach sunsets.