Description: Pillbox Trail features amazing views and interesting WWII-era observation pillboxes
Location: Lanikai, on Oahu’s east coast
Distance: Varies, but a novice could reach the second pillbox in 30-40 minutes
Difficulty: beginner
Danger: low, but watch out for heat and sun exposure, and be careful at the surprisingly slippery start
Suitable for: beginner to intermediate
Gear: At least 2 liters of water, a snack, sunglasses, and sunscreen
Time: 1 hour to 90 minutes, round trip, to the second pillbox
Lanikai Pillbox Trail is located in Lanikai, a posh neighborhood adjacent to Kailua, situated on Oahu’s east side. The trail is generally easy; although the very beginning is a slippery ascent, you’ll be walking across a safe, novice-level ridge with gorgeous views in a matter of minutes. Be sure to bring sunblock and extra water; although the terrain isn’t dangerous, the heat is usually intense. The trail is dog friendly, but be sure to bring plenty of extra ice-water to keep your K9 friends hydrated and cool with periodic showers.













