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Most families head to famous Hanauma Bay on Oahu’s southeastern shore for its brilliant snorkeling and pristine beach. The nature preserve is widely considered one of the best snorkeling spots in the world. Few people realize that there is a very nice hike that traverses the ridgeline above the bay and takes hikers to the end of Pai’olu’olu Point and offers some spectacular views of the bay and surrounding coastline. The trail starts near the entrance to the preserve just behind the city bus stop located on the makai side of Kalanianaole Highway near the intersection of Hanauma Bay Drive. The trailhead is the gated paved road that goes off to the right, initially paralleling Kalanianaole Highway before turning left towards the ocean. There are a few parking spots next to the gate behind the bus stop. We are not sure if these are real parking spots or not, so park there at your own risk (we saw vehicles there the day we went but decided not to risk it!). If you chose to park in the Hanauma Bay parking lot ($1.00), there is a paved walkway that leads from the lot up the hill to the park entrance and trailhead. There is also parking available at Koko Head Regional Park across Kalanianaole Highway and a dirt trail that leads back to the park entrance or lastly, there is street side parking along Nawiliwili Street (the last road to the right before the park that turns into a residential area. There may be a side trail from Nawiliwili Street to the trail, we saw one that looked like it went that direction but we didn’t follow it to verify. If you can not find it or it does not lead to the trail, head up the side of Kalanianaole Highway to the bus stop and pick up the trailhead there. Once you park and get to the trailhead, hop the gate or go around and head up the paved path. The paved path follows the ridgeline and eventually takes you to the top of the hill near some FAA and radio towers. This stretch of the hike is about a mile long and is almost all uphill. We would consider the path stroller accessible not necessarily stroller friendly because of the incline! It’s all uphill and fully exposed to the sun so it’s a workout! There are beautiful views of the bay below and, on the opposite side of the ridge, you can see Diamond Head, Hawaii Kai, and Maunalua Bay. There are also terrific views of the channel between Oahu and Molokai which is an excellent place to watch for whales in the winter time! We saw lots of tail slaps, spouts, and breaches as we hiked! Once the pavement ends, there is a dirt and loose gravel path that heads downhill to the east and out to the end of Pai’olu’olu Point. The trail makes a loop around the point before merging back into the paved road for the return hike back to parking. (Note: You can also access this portion of the trail prior to the towers and do the loop in the opposite direction, look for the red dirt trails going off to the left towards the bay as you ascend the hill near the towers.) There is a very steep section near the paved road (depends on which direction you take out to the point if it is at the beginning or end of your journey) that is extremely difficult to maneuver. Take your time in this stretch. A slip could be disastrous. Use extreme caution on the dirt loop around the point if you take your kids. Because of the loose terrain and inclines we recommend not taking the younger kids on this portion of the trail, stick to the paved portion! Better leave this to the older kids, at least in the 10+ age range. If you chose to take your younger kids in a carrier, exercise extreme caution! The hike is doable but the trail conditions make a fall a good possibility! The dirt portion is inaccessible for strollers. The trail is fully exposed to the sun, there is no shade of any kind! For this reason, we recommend doing this hike in the morning before temperatures peak for the day. Remember to pack your camera, lots of water, plenty of sun screen, sun glasses and a hat. Sturdy hiking shoes are a must on the dirt section of the trail. Walking or running shoes are fine for the paved section. There are no facilities along the trail but there are full facilities available at Hanuama Bay. The views along the trail are phenomenal and make this a worthy hike. It is little used although we did see some dog walkers and power walkers on the paved trail that seemed to be regular users. For young families, stick to the paved portion, there is still plenty to see and its still a great workout! If you are more adventurous, take the dirt trail around the point, but use caution, come prepared and take your time!