Proposal planning
Where is the best place to propose on Oahu?
Answered by Hawaii Glider Rides
The answers
In the air over the North ShorePrivateAsked most
A glider ride from Dillingham Airfield carries you, your partner and the pilot. Nobody else. There is no engine, so it is quiet enough to say it out loud and hear the answer. Book the 60-minute flight for two so you are not rushed, add the photo and video package so you have it on film, and email us after booking. The pilot keeps the secret.
Lanikai Pillbox at sunriseEarly start
A short, steep trail in Kailua with a view over the Mokulua islands. Go up in the dark and ask as the sun comes up. Parking is on residential streets and fills early, so arrive before 5:30 and keep the noise down for the neighbors.
Lanikai BeachSunrise
Same sunrise, no climb. The sand is soft, the water is calm and the two islands sit in the frame. Weekday mornings are quiet. Weekends are not.
Tantalus LookoutSunset
Puʻu ʻUalakaʻa State Wayside on the drive above Honolulu, with the whole city and Diamond Head below. It closes around sunset, so check the gate hours and get there 45 minutes early.
Makapuʻu Point trailViews
A paved walk up to a lighthouse lookout on the east tip of the island. Whales in winter, the Koʻolau cliffs all year. Go on a weekday morning before the heat and the crowds.
Waimea BayNorth Shore
Big surf in winter, glassy water in summer. The rock on the north end is the spot. In summer you can swim out after. In winter, stay on the sand and let the waves be the show.
Diamond Head summitReserve ahead
The classic. Reservations are required for visitors and the trail opens at 6. Go for the first slot, ask at the top, and be down before it gets hot.
Byodo-In TempleQuiet
A replica Japanese temple at the foot of the Koʻolau cliffs in Kāneʻohe. Koi ponds, a bell, and a green wall of mountain behind you. Small entry fee, and it is calm even on busy days.
Kaʻena PointRemote
The far west tip of the island, reached on foot from the end of the road past Mokulēia. Albatross nest here in winter and monk seals rest on the rocks. Two and a half miles each way, no shade, and almost nobody around.
Halona Blowhole lookoutEasy access
A roadside lookout on the southeast coast with the blowhole, the little cove below it and Molokai on the horizon. Park, walk 30 seconds, done. Best in the morning before the tour buses.
Haleʻiwa harbor at duskCasual
If you want low-key, walk out on the breakwater at Haleʻiwa boat harbor as the sun drops toward Kaʻena. Shave ice first, dinner in town after.