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May 1, 2020

Hawaii Engagement Photos & Surprise Proposal: Planning Guide


Last Updated on April 9, 2024 by Karma Hill

Everyone dreams of proposing to Mr. or Mrs. Right!! There’s no doubt that people are made to love. Just look at how many love songs exist! It’s easily the most inspiring sensation in life, and we want to help you bottle it up and frame it! Together, we’ll capture the moment of pure surprise and joy on your special someone’s face with sweet Hawaii engagement photos

We’re often asked to help plan proposals: “Where do we go?” “What do I do?” “I know I want it photographed but that’s all I know!” “I have a ring!” 

Well, that’s a great start! Now sit back and relax because we’re happy to guide you through the rest!

During the planning process, we’ll help make this giant event seamless and easy. We’re here to listen to any ideas that you come up with along the way. Keep us updated as you learn of your travel plans, like where you’re staying or even where you plan to celebrate afterward! With these little pieces of information, we can give you our professional opinion and suggestions to give you all the confidence you need to pop the Big Question at the Perfect Moment. 

We did just that with the clients you’ll see below! Come along and immerse yourself in the absolutely timeless and heartfelt sessions of our recent Hawaii surprise proposals. We’ll go over all the many engagement styles to help you plan that special moment. 

Option 1: The Love Ninja

Most of our clients choose to keep their surprise proposal in Hawaii simple and romantic with a walk down the beach. We’ll work with you to coordinate the perfect time and place.

You’ll send us a picture of the two of you and we’ll share a picture of your Hawaii engagement photographer. That way we can ensure we’re looking for the right people. Our photographers are also great actors, so they’ll be practicing their “Where’s Waldo” skills by blending in as a beachgoer taking pictures of the scenery, the waves, the sand… anything other than you! We wouldn’t want to spoil the surprise too soon!

Sometimes the photographer will even get incognito and practice their ninja skills by ducking down behind a bush while you pop the question, all to capture the perfect Hawaii engagement photos. And that’s exactly what happened during Anthony & Olivia’s special moment…

Maui engagement photos
Anthony & Olivia • Napili Bay, Maui

Will my partner figure it out?

The goal is straightforward: take a nice walk along the beach.

I mean, that’s not suspicious; you’re in Hawaii, on a gorgeous beach, and who doesn’t want to take in the scenery? Not saying they won’t have an inkling of an idea… but as soon as that knee hits the sand all the emotions come flooding in! Just check out Bailee’s reaction in the Hawaii engagement photos below…

engaged on Oahu - best photographers for surprise proposals
Bailee & Shane • Makua Beach, Oahu

That said, all Hawaii beaches are public, and sometimes unexpected things happen. It’s best to just go with the flow. Logan planned a beautiful surprise proposal on Ironwoods Beach, and our photographer was waiting (incognito, of course!). Everything was going as planned, but just as he was about to get down on one knee, a little elderly woman toddled by and blocked the photographer’s view! Luckily, Logan was on full-force observation mode and quickly noted it, waiting until the coast was clear before he made his epic Maui surprise proposal! David’s sweet smile had us all charmed!

surprise proposal in maui - same sex couple - maui photographer
Logan & David • Ironwoods

There is no better feeling in the world than to have the person you want to spend your life with feel the same way. That step you take to start your life as a married couple is like no other! Revel in it, soak it up, and then once you turn around, you’ll realize we were there to document it all! Below, Brianne’s giddy expression of shock and delight says it all…

Maui engagement photographer
Breanne & Brody • Southside Beach, Maui

They said “Yes!” Now what happens?

We’ll give you a couple of minutes to celebrate getting engaged and live in that joyous moment ~ then the rest of the fun begins! Your Hawaii engagement photographer will come up, congratulate you, and introduce themselves! The rest of the hour is yours to keep. It becomes a surprise proposal turned engagement session!

Your photographer will then guide you along the shore to capture the most beautiful Hawaii engagement photos possible!

engaged on Maui - beach proposal photography - Hawaii engagement photos
Brooke & Robert • Polo Beach, Maui

What can I do to help?

It’s very important during this planning process that you somehow get your significant other to get dressed up.

We suggest having dinner plans afterward and letting them know that you’re going to take a nice walk along the beach first. That way they aren’t wondering why you’re getting dolled up to go to the beach.

Everyone feels the most comfortable when they look their best. Check out Brooke & Robert pictured above! Their fancy dinner-date attire really makes the pictures pop! If you’re most comfortable in surf shorts or a bikini then that works too! Whatever makes you (and your partner) feel your best!!

Option 2: The Family Affair

Another great way to surprise your love is to make them think you’re just having a family photo session!

Everyone gets excited and dressed up for family portraits, and what better opportunity to ask for their hand in marriage than when you have a photographer already there and your family supporting you?

Griffin & Jenny, pictured below, are high school sweethearts. They were here on the island with their family and Griffin planned a special Maui surprise proposal for his lady! About 20 minutes into their family portrait session we transitioned into taking pictures of just the two of them.

Much to her surprise, he dropped to one knee and asked her to be his girl forever! Such a special moment, she was beyond elated, and we were there to document it with gorgeous Hawaii engagement photos!

engaged on Maui - ironwoods - proposal photography
Griffin & Jenny • Ironwoods Beach, Maui

Andrew had a similar plan when he proposed to Briana (pictured below). He organized a family portrait with their loving family, and once he popped the question, the whole crew was there to cheer them on! Who said getting engaged on Maui has to be a moment shared between just the two of you? I mean, you are marrying their family as well!

Hawaii engagement photographer
Briana & Andrew • Baldwin Beach, Maui

Option 3: The Not-So-Secret Surprise

Marcus just knew that surprising Taylor with a walk on the beach was NOT going to happen. Some people can just feel it coming, and you have to be a little trickier!

In that case, we suggest having a couple’s portrait! Just a good ole’ couples portrait in Maui shouldn’t raise any flags, right? The night before, you could even trick her with a romantic dinner where she thinks it’s coming… but it doesn’t. Is that mean? Well, we think it’s fun!

Make her think you’ve booked a portrait to commemorate your time in Hawaii together. The photographer will set you up behind her, and as she’s getting some individual shots taken ~ BAM! Down on one knee, she makes the turn, and there you are! Asking for her hand in marriage. It worked like a charm for Marcus, and Taylor was ecstatic!! How sweet are these Hawaii proposal photos??

get engaged on Maui - surprise proposal on beach - hawaii engagement photos
Taylor & Marcus • Polo Beach, Maui

Option 4: A Table For Two Please

The romance doesn’t have to end at the beach.

You can also plan a romantic dinner and propose in a venue setting like the garden at the Hotel Wailea, just as Aman & Chhavi did! The fabulous Hotel Wailea coordinators helped Aman plan the occasion, and we had our photographer there, hiding in the bushes, of course, ready to capture the moment!

Afterward, they enjoyed a champagne toast (which you aren’t able to do on the beach due to state laws) and then an engagement photography session. It was a moment to cherish, and we were honored to capture it for them!

Hawaii engagement photographer
Chhavi & Aman • Hotel Wailea

Is there a location that’s both a venue and a beach?

If your heart is set on asking the big question on the beach but you also want the sophistication of a spectacular venue, then consider booking a dinner at the lovely Four Seasons Resort! Grant proposed to Mollie during a sunset stroll down Wailea Beach. Of course, She Said Yes! Then they celebrated with a portrait session and a beautiful dinner overlooking the cherished spot where they became engaged in Maui.

engaged on Maui
Mollie & Grant • Wailea Beach + Four Seasons Resort, Maui

Option 5: Doing What You Love

There’s nothing quite like doing what you love together as a couple. Hawaii may be a tropical paradise, but it’s also filled to the brim with spectacular activity options. No matter what your forte is, you’ll find something in the islands to satisfy any hobbyist’s dreams. So why not propose while doing what you love?

Zach did just that, and we were thrilled to help him capture the big moment! As a couple, they’ve traveled around the world and love to be outdoors, so Zach felt a morning hike up Maui’s Waihe’e Ridge Trail was the perfect Maui proposal spot. We worked out the details, and by the time they reached the lookout point, our photographer was peeking out from the bushes, camera-ready! He got down on one knee as they were enveloped in a cloud of mist. Kelly’s reaction says it all!

Kelly & Zach • Waihe’e Ridge Trail

Proposals are so special, and we want to help you capture this special moment with the best Hawaii engagement photographer! We’ll help bring your dream into reality. Our professional staff and team are more than willing to help guide you into making the most of this life-changing occasion.

Ready to take the big leap? Come check out our beautiful Maui couples photography packages.

Karma Hill - Hawaii
Owner | Website

Karma Hill is the owner of Karma Hill Photography, Simple Maui Wedding, Simple Oahu Wedding, and Simple Hawaii Wedding, marking a significant presence in the Hawaii wedding community since 2007. With a wealth of experience and a vast collection of informative posts on weddings and photography in Hawaii, Karma Hill offers unparalleled expertise. Explore the world of photography and wedding planning across Hawaii by visiting Karma's websites.

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