Haley started tearing up when Ryan proposed on a beach in Lahaina on their 10 anniversary.

Lahaina Proposal at the Beach

We planned Ryan’s Lahaina proposal around existing dinner reservations, so Haley wouldn’t suspect a thing.

Ideally, you would come to us early, before you have any activities set in stone for your Maui vacation, so we can pick your proposal date and everything can be planned around your big moment. Popping the question on your first or second full day when you don’t have much to do (besides a nice dinner) is usually best case scenario.

Since proposals are a surprise (they often know it’s coming but not where or when), keeping your schedule open can be tough.

One thing we recommend doing is telling your sweetie you would like one or two days of the vacation to plan. Having two days of your own to plan is nice because you can use one of those days to either throw them off your scent or have some surprises to kick off the celebration of your engagement the day after the proposal.

However, if your other half is the planner in your relationship, then this request can raise too much suspicion. Or clients find Engaged on Maui when their itinerary is already full.

When your itinerary is action-packed, we have to find openings and locations that will work with your plans. The downside is that it can force us to plan proposals at times we wouldn’t normally shoot at because lighting is very hard to work with. The upside is that your proposal fits so well into your itinerary, they won’t see it coming.


Ryan came to us wanting to propose to Haley on a very special date – their 10th anniversary! They had dinner reservations at Fleetwood’s on Front St. for the occasion. They were already planning on checking out Lahaina town before dinner so figuring out a beach in Lahaina was the way to go.

Ryan wanted to keep his Lahaina proposal simple. They had a lot of activities planned and he preferred to pop the question on one of their chill days.

We know the instinct can be to go big and over-the-top, especially when you see proposals like that on social media, but honestly so many of our favorite proposals are simple and heartfelt. The emphasis is kept on the couple, their love, and the commitment they are making to each other.


On that day, our photographer Tim discreetly waited for Ryan and Haley at the start of the beach. It was a little bit of a walk to the proposal spot, so Tim secretly followed them to make sure he could capture Ryan getting down on one knee.

Haley must have had a suspicion, or at least a hope, that Ryan would propose on their anniversary, but her reaction was still surprised and then overjoyed.


For beach sessions, we normally plan timing at sunrise, early morning, or ending at sunset for the most flattering lighting.

Ryan and Haley’s dinner reservation was before sunset and we had to give them enough time to get from the beach to the restaurant. We knew with the timing, their lighting wouldn’t be as soft as we like and they would miss any sunset colors, but Tim made it work. Ideal lighting or not, their love shines! Ryan and Haley have been together through high school, college, and beyond, so it was an incredible honor to be part of this huge steps in their lives!

Engaged on Maui photographer secretly followed our couple to their proposal spot on a beach in Lahaina.

Haley was so surprised when Ryan dropped down on one knee in Lahaina, Maui.

Haley started tearing up when Ryan proposed on a beach in Lahaina on their 10 anniversary.

Ryan pulling out Haley's engagement ring as he popped the question on a Lahaina beach.

Lahaina Beach proposal

Simple proposal in Lahaina, Hawaii

Ryan proposed on the beach in Hawaii and Haley dropped to her knees too.

Ryan proposed on one knee and Haley dropped to her knees to hug him.

Ryan and Haley hug after he proposed on a beach in Lahaina, Hawaii.

Couple sits on a sandy beach nestled again naupaka as they celebrate their engagement.

Ryan and Haley stroll down the beach in Lahaina after their engagement.

Ryan and Haley stand by the ocean under the palm trees as he kisses her cheek.

Haley looks into Ryan's eyes and puts her hands around his neck.

Ryan and Haley stand on a beach in Lahaina, smiling at each other and touching noses.

Ryan and Haley kiss and she holds his chin between her pointer finger and thumb.

Ryan and Haley hold her hand with her engagement ring in front of the ocean.

Ryan stands in the shore break and Haley jumps into his arms as he picks her up.

Ryan lifts Haley up and she bends one knee to point her toes..

Ryan and Haley kiss on a Lahaina beach after their proposal.

Ryan and Haley: Thank you so much for your trust. Here’s to your first decade together and many many more to come!

Photographed by Associate Tim | Simple Proposal

Contact us to get started on planning your Maui proposal!

Similar Posts