One Weekend on Oahu: A Complete 3-day Itinerary

After you snag a parking spot, head up on the clearly marked trail to the overlook. It’s just over 1 mile to the top, but you will be sharing this paved trail with a LOT of other people. No worries though as it was wide enough for us to pass and walk at our own pace AND the views are worth it. Once at the top, you can watch for nearby hang gliders, check out the lighthouse, and even watch for the migrating humpback whales (if visiting in the winter).

Next on the list is the Lanikai Pillbox hike. It’s about 20 minutes from the Makapu’u Point trail. After arriving, you’ll quickly realize there is not a parking lot, so you do need to find parking along the residential streets. Just be sure to pay attention to signs and not block any driveways. After snatching a parking spot, head to the trailhead (google maps will lead you there if you are lost) and start the climb. After less than a half mile, you’ll first see the first Pillbox, but if you keep going a bit further you’ll reach the second. It’s a great place to relax, have a snack, and enjoy the view.

After your hike, I recommend spending some time at Lanikai Beach (since you already have a parking spot). Spend an hour or two soaking up the rays or having a picnic along the shore!