A dream destination proposal on Oahu isn’t just about love, it’s about going on an adventure with the love of your life! What better way to kick start your Oahu vacation by going on a hiking adventure and proposing to your partner in crime?

I recently received more requests to chase the sunrise on an adventure proposal around the island of Oahu! Way back when I first started, I remembered I wouldn’t be too thrilled. Hiking with 20 lbs of gear is a lot of work! Not to mention the mosquitoes, hot sun, and trying to keep my footing while not falling off a cliffside! The younger me would have done everything possible to avoid the early 4 am wake up call. Although, the older me loves to chase the sunrise and is definitely not one to back down from a bit of a challenge (as long as there is lots of mosquito repellent and sunscreen).

My sunrise proposal scouting adventure

This morning my little sunrise proposal scouting adventure took me to the Lanikai PillBox hike, also known as Kaiwa Ridge Trail. This hike is voted as one of the things to do on Oahu and is a local favorite! Even though I have done this hike many times before, I’m always so blown away by the stunning views of the Windward coast and how absolutely gorgeous the sunrise is! If you can’t tell by now, I’m in love with the sunrise and Kailua has hands down, the best sunrise on the island of Oahu, Hawaii! Also, the town of Kailua is considered the countryside of Oahu, aka what Oahu might have been like if we stepped back in time.

The downside is that there are no restrooms and the parking is dreadful! The nearest restroom is at Kailua beach which is all the way down the hill! Speaking of hills...I always have the worst parking experiences there. I parked a few blocks away, which was fine. I wanted to go on a hike so why not start at the bottom of the hill? It was a good warm up for the actual hike and The trailhead is right across the Mid-Pacific Country club.

The hike itself is rated intermediate and “family friendly,” but honestly… I would not recommend taking small children here, try Makapu’u lighthouse trail first! This trail is a very steep uphill battle. It's an intense 20-30 minutes to the first pillbox. There are 2 places for rest stops in between, but then viola! The reward of fantastic views of the Windward coast and the Mokulua Islands await.

There are also several spots here which are worthy of such an adventurous couple who wish to chase the brilliant Oahu sunrise and propose in our Hawaii Paradise! Is this something that speaks to you?

I hope that this brought you some inspiration to plan your big moment! Need more inspiration? Check out some of our other blogs and our Adventurer Hawaii Proposal Package. We specialize in creating that perfect surprise engagement that you’ve been envisioning! Are you ready to plan your Dream Destination Proposal on Oahu? We can help you with all the planning, logistics, and set up to make everything as smooth (and painless) as possible. Send us a message! Let’s tell your love story!