How to Propose in Maui Hawaii

I’ve been asked many times how one can propose marriage creatively on our island. I tell my own story, and then give suggestions. It’s time to share this with everyone.

How I Proposed to my wife on Maui

We live here, so I felt that I needed to do more than just walk down the beach and propose (though it would have sufficed.) I rented a beautiful house in Hana and told my girlfriend that I’m taking her camping in Hana.

My lady is notorious for sleeping in (as am I), so I woke up early and packed everything I needed for a weekend at the house. I added a few camping accessories to seal the deal. When she woke up, she marveled at how I’d packed the car already. We left early for the Road to Hana.

Once we arrived, my lady was very surprised about the house and asked what occasion we were celebrating. This is where I blew it. I should’ve made something up, but I said it was for some spontaneous fun. Bad liar. She knew something was up.

I immediately began setting up a picnic on our property (great views!) The day before, I’d visited Who Cut The Cheese in Kihei to pick up some wine and cheese. Despite the horrific name, this shop is something really special. The woman working there helped me pair some of my favorite cheeses with some half-bottles of wine.

During the picnic, I nervously unpacked each cheese as we sipped on complimentary splits. It was great! Then, as we savored a french grape-leaf-wrapped goat cheese, I proposed to her. It went off pretty damned well. We then spent the next 4 days running around Hana, hiking, swimming, exploring, and relaxing. The perfect start to our engagement.  (And today we celebrate our 3 year anniversary! I love you, honey!)

My one regret is not having the ability to wait a little longer to propose under a beautiful waterfall we’d discovered the next day. There was NO WAY I could hold out for a whole night without relieving myself of the burden of holding all of this in, so I proposed immediately when we got there (that would be 1 long sleepless night in Hana.) It would have been cool though If I’d swam up to her under the waterfall with the ring (so long as I didn’t drop it.)

Here are a few ideas I have about some unique ways to propose to your woman while visiting Maui, Hawaii.

1. Picnic on the beach – You can find a spot on a low-density beach or on a grassy bluff along the water. Sunsets are a great idea for both #1 and #2 if on the South or West side.

2. Walk on a deserted beach – Try some of the long stretches between North Kihei and Maalaea or go up North to some of the kite beaches. Most of these are long and don’t have many occupants.

3. Go on a hike and find a waterfall – Wait for any other hikers to leave before popping the question. Bring a little bottle of champagne or sparkling cider. If you don’t know of any less-traveled hikes, have a local take you up to a good waterfall, then have them leave. This only works if you’ve got friends on the island, or if you find someone nice enough to do this for you. (Consider calling around for a private tour like this.  If the hiking tours out there don’t already have one, they should.)

4. Propose while fine dining – We’re not talking about hitting up Outback or Applebys. Reserve a secluded table at Ferraros at the Four Seasons or at Capische. Dress nice and order some good wine. Take your time with a long meal and propose whenever you want. See a list of Maui restaurants.

5. Go on a cocktail sunset cruise – You can take a trip on the Kai Kanani or another vessel that doesn’t have too many people on it, or if you’ve got the bucks, charter a private cruise on the Island Star. The later would be preferred. If you can go sailing in Maui, that would be the best since you get less fumes and noise.  Plus it’s more romantic than a power boat.

6. Take a drive – There are many gorgeous spots to stop and enjoy Maui views. You might want to drive around exploring, and once you find the perfect spot, drop to a knee.

Remember: Always get down on your knee! make some effort. You don’t want your future wife to be telling a lame story for the rest of your lives.

I hope this helps. If you can think of any other ideas, give us a shout.

Maui Proposal Photos

Planning on getting engaged on Maui?  Natalie Brown Photography offers photography of those special moments when you pop the big question.  She works with the groom to set up a location where she can hide and shoot spontaneous photos of your Maui proposal!  Learn more about Maui Proposal photography or call (808) 344-3843.