Their proposal took place along a small pathway leading to a scenic overlook, where glowing “Marry Me” marquee letters and vibrant florals created a beautiful surprise waiting just ahead. It was colorful, joyful, and full of intention. The perfect propoasl for a couple whose love had been built patiently over time.

Andy and Joy are a little different from many of the couples we work with. This will be the second marriage for both of them, and their story is a reminder that love doesn’t follow a single timeline. Sometimes the most meaningful relationships arrive later in life, after experiences that shape you and teach you what truly matters.

When Andy first shared their story with us, it was clear how much respect and admiration he had for Joy. The two met nearly ten years ago at work in a setting that wasn’t exactly designed for romance. Joy was an attorney representing the department in a lawsuit, and Andy worked in law enforcement as the subject matter expert for the case. Their first interaction was professional, an interview for the case, but once the conversation started, it simply never stopped.

What began as work-related communication gradually turned into something more. They kept talking, kept connecting, and over time discovered just how naturally their lives fit together.

The Plan

Andy knew he wanted to create something special for Joy—something that felt celebratory without being over the top. He loved the idea of a scenic location that would allow the moment to unfold naturally, with a surprise waiting for her at the end.

We designed a romantic pathway leading to a stunning overlook, where the big reveal would take place. Along the ground, colorful florals were arranged to create a vibrant, welcoming space. The bright blooms added warmth and personality, reflecting the joy and energy that Andy described in their relationship.

At the center of the setup were glowing “Marry Me” marquee letters, positioned perfectly so that Joy would see them as soon as they reached the overlook. The combination of the dramatic view, the colorful flowers, and the soft glow of the letters created a setting that felt both romantic and playful.

The plan was simple: Andy would guide Joy down the pathway as if they were simply exploring the area together. When they reached the overlook and the proposal setup came into view, he would pause, share what was on his heart, and ask the question he had been waiting years to ask.

What made this proposal particularly meaningful was the history behind it.

For many years, Andy and Joy lived five hours apart. Their children were settled in their respective hometowns, so relocating right away wasn’t an option.

Instead, they made long distance work.

For years they built their relationship across those miles. Visiting each other, sharing conversations, and showing up for one another whenever life allowed. It wasn’t always easy, but it revealed something important.

Andy realized that no matter the distance, the happiest moments of his life were always the ones spent with Joy.

Two years ago, after both of their sons graduated high school, the timing finally felt right. Andy moved closer to Joy, and together they purchased a home in nearby. After years of visits and long drives, they were finally building a shared life under one roof.

The proposal on Maui wasn’t just about asking Joy to marry him…it was about celebrating everything they had already built together.

The Proposal

On the day of the proposal, the Maui landscape looked almost cinematic. The pathway leading to the overlook felt peaceful and quiet, with the vibrant flowers waiting just beyond view.

Andy led Joy along the trail, taking in the scenery as they walked. She had no idea that just a few steps ahead, a surprise was waiting that would mark the beginning of their next chapter.

As they approached the overlook, the setup slowly came into view. The colorful florals lined the ground, bright against the natural surroundings, and the glowing “Marry Me” letters stood proudly at the center of it all.

It was a moment of realization…the kind where everything suddenly clicks.

Andy took Joy’s hands and shared what had been on his heart for years. He spoke about the journey they had taken together, from that first conversation during a professional interview to the countless calls, visits, and shared moments that followed.

He reflected on the years they spent living five hours apart, finding ways to laugh and stay connected despite the distance. Those years showed him something important: their relationship wasn’t just built on love. It was built on partnership, resilience, and shared joy.

Through life’s biggest moments, even the difficult ones, they had always shown up for each other.

Somewhere along the way, as Andy described it, their relationship stopped being about “visits.” It became about a life they were building together.

With the scenic Maui overlook behind them and the colorful flowers surrounding them, Andy got down on one knee and asked Joy to marry him.

Joy’s answer was exactly what he had hoped for.

Yes.

The moment was filled with laughter, emotion, and the quiet kind of happiness that comes from knowing you’ve found the right person to walk through life with.

What made Andy and Joy’s proposal so special wasn’t just the beautiful setup or the breathtaking location. It was the depth of their story. Their love wasn’t rushed. It grew through years of distance, patience, and shared life experiences.

By the time they stood on that overlook in Maui, their relationship had already weathered real life—and come out stronger because of it.

At Engaged on Maui, it was an honor to help create the setting for such a meaningful moment. Andy and Joy’s proposal reminds us that love can arrive at any stage of life, and sometimes the most beautiful beginnings come after years of building something strong together.

And in this case, that next chapter began with colorful flowers, glowing marquee lights, and a simple question asked in one of the most beautiful places in the world.

Want to see similar scenic Maui proposals? Check out these blogs!
Romantic Maui Proposal | Maui Proposal with Marry Me Letters | Perfect Proposal on Maui

Check out our Pinterest to see other Proposal Inspiration!

The post Scenic Maui Proposal | Andy & Joy | Maui, Hawaii appeared first on Engaged on Maui | Maui Proposal Photographer.

When Brandon first reached out to Engaged on Maui, his timeline was short. Four days, to be exact. From initial contact to proposal day, we had less than a week to bring everything together. While that doesn’t allow for every elaborate detail or over-the-top installation, it doesn’t have to. Sometimes, sweet and simple is exactly what a love story needs.

And for Brandon and Alexis, simple was perfect.

Their story started when they were just 13 years old. Alexis was Brandon’s first serious girlfriend. “As serious as you can get at 13,” he joked. But even at that age, he knew he felt something different about her. She was all he could think about. He would catch the bus across town just to see her. They spent a year together before going to different high schools, and life naturally pulled them in different directions.

In the years that followed, Brandon joined the military and left home. Thirteen years passed without seeing or speaking to Alexis. Then one night, back in their hometown, they ran into each other. The connection was immediate. What they felt at 13 hadn’t disappeared, it had simply been waiting.

Now, with a home and two children together, Brandon knew Alexis deserved a proper proposal. She wasn’t just his first love but was the love of his life and the mother of his children. And Maui felt like the right place to honor that.

The Plan

With just four days to plan, we focused on what matters most: location, timing, and intention.

Last-minute proposals require flexibility. Certain custom builds and elaborate setups need more lead time, but a thoughtfully chosen beach at sunset? That’s always within reach and always breathtaking.

We selected a quiet stretch of beach that would allow Brandon and Alexis to feel like they had the island to themselves. No distraction or pressure. Just the sound of the waves and the glow of golden hour.

The design approach was minimal and romantic. When timelines are tight, keeping things sweet and simple ensures everything comes together seamlessly. It allows the emotion to take center stage rather than the décor.

Sunset timing was key. On Maui, the light shifts quickly, moving from warm gold to soft pink in a matter of minutes. Planning around that window meant Brandon would have the most beautiful natural backdrop possible without needing much else.

The focus wasn’t on extravagance. It was on giving Alexis a moment that felt intentional and long overdue.

The Proposal

As the sun began its slow descent toward the horizon, the beach glowed in soft gold. Brandon led Alexis down toward the shoreline, the waves gently rolling in behind them. The setting felt calm and effortless, the kind of evening you don’t have to force.

There’s something powerful about a simple proposal. Without elaborate distractions, every word carries more weight. Every pause feels deeper.

Then he got down on one knee.

With the Maui sunset painting the sky behind them, Brandon asked Alexis to marry him. It wasn’t flashy or overproduced. But instead it was steady, heartfelt, and full of history.

Alexis said yes.

In that moment, you could feel the years woven into it. The teenage crush, the separation, the reunion, the life they’ve already built. This wasn’t the start of their story. It was an affirmation of everything they’ve already created together.

Afterward, they lingered on the beach, soaking in the reality of what had just happened. The sky shifted from gold to blush to deep blue as they held each other and laughed. It felt relaxed and real and exactly like them.

Brandon’s desire to give Alexis a “proper proposal” wasn’t about grandeur. It was about intention. It was about pausing in the middle of a busy life with kids and responsibilities and saying, “You matter. This matters.”

For couples considering a last-minute proposal, Brandon and Alexis’ story is proof that you don’t need months of planning to create something meaningful. While we may not always be able to offer every bell and whistle on a four-day timeline, we can create something timeless. When you strip a proposal down to its core—beautiful scenery, thoughtful words, and genuine love—it becomes unforgettable.

Sweet and simple works. Especially when the foundation is this strong.

Brandon and Alexis’ sunset beach proposal will always remind us that love doesn’t expire. It can wait thirteen years. It can survive distance and time. And when the moment is right, it can come rushing back stronger than ever.

On a quiet beach in Maui, as the sun dipped below the horizon, a teenage love story was honored in the most beautiful way. And sometimes, that’s more than enough.

Looking for more sunset beach proposals? Check out these proposals!

Simple Maui Beach Proposal | Storyteller Proposal in Kihei | A Perfect Proposal on the Beach

Want more Proposal Inspiration? Follow us on Pinterest!

The post Sunset Beach Proposal | Brandon & Alexis | Wailea Beach appeared first on Engaged on Maui | Maui Proposal Photographer.

Pruthvi and Tithi have been together for nearly eight years, but their story started long before that. They grew up in the same town, spent years as friends, and slowly built a connection rooted in shared values, culture, and genuine admiration for one another. From the beginning, Pruthvi knew Tithi was special. Her love for family, her ambition, her carefree spirit, and the way she brought her Indian and Hindu culture into his life in such a meaningful way.

So when it came time to propose, Pruthvi knew this moment had to reflect who she is: simple, beautiful, intentional, and full of heart. And he wanted it to be a complete surprise.

The Plan: A White Lotus–Inspired Beach Proposal in Maui

Planning a surprise proposal in Maui from New Jersey is no small task… and Pruthvi was the first to admit that planning wasn’t his strong suit. That’s where we came in.

From the very first conversation, Pruthvi shared his vision clearly. He loved the look of our White Lotus–inspired beach proposals. A soft, elegant setup with a floral entrance, candles lining the path, and a romantic focal point at the end. He wanted sunset timing for the most picturesque light, no oversized “Marry Me” sign (because Tithi prefers simple elegance), and a setting that felt private and emotional rather than flashy.

The biggest piece of the plan? The surprise.

Tithi was already on a girls trip in Maui with her sister, completely unaware that Pruthvi — along with her cousins, siblings, and his sister — were secretly flying in as well. The first time she would see Pruthvi wasn’t at the airport or hotel… it would be when he was standing in front of her on the beach, ready to ask the biggest question of his life.

Together, we chose this private venue in West Maui, a breathtaking private estate that offers a secluded beachfront feel, palm trees swaying overhead, and golden sunset views. The perfect backdrop for an intimate Maui proposal. We coordinated timelines, permits, photography, décor, and logistics, making sure everything flowed seamlessly while keeping the surprise intact.

Every floral detail and step along the path was designed to feel romantic, peaceful, and intentional… a reflection of Tithi’s personality and the life they’ve built together.

The Proposal: A Sunset Surprise, Followed by an Even Bigger One

As the sun dipped lower and the sky began to glow, Tithi arrived at the venue expecting nothing more than a beautiful evening in Maui. What she didn’t expect was to see Pruthvi standing at the end of a floral pathway, waiting for her.

The look on her face said everything.

Shock. Joy. Tears. Laughter. The kind of reaction that only comes when your heart is completely overwhelmed in the best way possible.

As she walked toward him, surrounded by flowers and the sound of the ocean behind her, Pruthvi did what he’s known all along — he chose her. He spoke from the heart, honoring their years of friendship, their shared culture, their love for family, and the future he couldn’t imagine without her. And when he dropped to one knee at sunset, with Maui glowing all around them, Tithi said yes.

But the surprises weren’t over yet.

Just moments after the proposal, her family stepped out onto the lookout. Cousins, siblings, loved ones who had traveled all this way in secret to be there for this moment. The tears came again, the hugs were endless, and the beach filled with laughter, joy, and celebration.

Afterward, we captured a mini engagement session, allowing Pruthvi and Tithi to soak in the moment, breathe, laugh, and begin this new chapter together.

Why This Maui Proposal Was So Special

Pruthvi and Tithi’s proposal was a reminder that the most meaningful proposals aren’t about being the biggest or boldest. They’re about being intentional. Every detail reflected who they are: simple, family-oriented, deeply connected, and full of love.

At Engaged on Maui, this is exactly why we do what we do. We help bring long-distance planning, surprise logistics, and heartfelt visions together so couples can focus on what truly matters. The moment they choose forever.

Pruthvi planned this proposal with so much care, and Tithi felt every bit of it. Their story proves that love doesn’t need a script… it just needs honesty, intention, and a setting as beautiful as Maui to hold it all.

Pruthvi & Tithi, your love radiates. And it was an honor to help you begin this next chapter together

Looking for more proposal inspiration like this one? Check out these blogs!

Romantic White Orchid Beach House Proposal | Maui Picnic Proposal with Marry Me Letters | Picnic Proposal at Wailea Beach Resort

Check out our Pinterest for more proposal photos and proposal inspiration!

The post A Surprise Romantic Proposal | Pruthvi & Tithi | Private Palm Venue appeared first on Engaged on Maui | Maui Proposal Photographer.

Patrick and Rachel’s Maui picnic proposal was exactly that kind of moment. It wasn’t just about asking a question. It was about honoring a love story that began in childhood, wove its way through time, and found its home again years later. It was about gratitude, second chances, and the promise to show up for each other again and again.

Helping Patrick bring this vision to life was an honor from start to finish.

The Plan

When Patrick first reached out to Engaged on Maui, he wasn’t looking for something flashy…he was looking for something meaningful. He shared their story with us: how he and Rachel grew up in the same hometown, met through mutual friends, and briefly dated when they were young. Life eventually pulled them in different directions, the way it often does, but fate had something else in mind.

Years later, they ran into each other at a mutual friend’s Christmas party. One night was all it took for everything to fall into place again. As Patrick explained it, Rachel first caught his attention with her beauty, but it was her heart—her kindness, her care, the way she shows up for people—that anchored him for good.

Their relationship grew into a life filled with laughter, warmth, and a household full of furry (and feathered) family members. Three dogs and a bird keep the home lively, and their love for animals reflects the love they’ve built together.

Patrick also shared something incredibly honest: they got married 12 years ago in the simplest way possible. No grand proposal. No celebration. Just a conversation on their back porch and a courthouse visit, mainly so Rachel could get on his insurance. They planned to keep it quiet, but as he joked, “small towns don’t work that way.”

Even after all these years, Patrick carried the weight of not giving her the moments she deserved. There was no dream proposal, no perfect wedding day to look back on, no honeymoon photos to hang on the wall.

So when he told us he wanted to propose again, but this time with intention, emotion, and beauty. We knew this moment needed to feel special.

We planned a romantic beachside picnic at one of White Orchid Beach House. Soft pillows, little snacks, florals that felt both warm and elegant, and a secluded layout that allowed the two of them to simply be together. The goal: create a peaceful space where time could slow down and memory could take shape.

Patrick wanted everything to feel heartfelt, simple, and beautiful. A place worthy of the words he wanted to say to her. And most importantly, a moment that felt like theirs.

The Proposal

When the day arrived, the Maui sun dipped behind thin clouds, casting a soft golden light across the shoreline. The ocean sat calm, the breeze gentle, and the world seemed to make room for their moment.

Patrick and Rachel arrived at the picnic spot, both taking in the scene with quiet awe. Rachel thought they were simply enjoying a sunset date on their trip—nothing more. But Patrick’s heart was already racing for what came next.

As they walked over to the picnic and listened to the private musician, Patrick took a breath. This wasn’t just a proposal. It was the culmination of twelve years of wanting to give her everything she had missed the first time. Twelve years of knowing she deserved magic. Twelve years of loving her in all the big and little ways.

When he pulled out the ring, Rachel’s expression softened into pure emotion. She wasn’t expecting it—not here, not now, not this way. But the moment felt right in every possible sense.

There with the ocean meeting the horizon and the glow of their picnic beside them, Patrick asked her to marry him again. This time with intention, with joy, and with the celebration she always deserved.

She said yes.
Of course she did.

The two of them held each other close as the waves rolled in, the sky shifted to warm sunset tones. It was simple. It was heartfelt. It was everything he hoped to give her.

Patrick and Rachel’s picnic proposal was a reminder of what love looks like when it grows, evolves, and deepens over years. Not every love story starts with grandeur—but every love story deserves moments that take your breath away.

And it was our honor to help create one of theirs.

Want to see more picnic proposals like Patrick and Rachels? Check out them out here!

Looking for more proposal inspiration? Check out our Pinterest page!

The post A Maui Picnic Proposal |Patrick + Rachel | White Orchid Beach House appeared first on Engaged on Maui | Maui Proposal Photographer.

William already knew without a doubt that she was the one. After all, she wasn’t just his high school sweetheart. She was the girl who lived just a minute away. Roshni got to share all of life’s firsts with him, the girl next door who became his whole world. He could go on forever about all the reasons he loves her, but what mattered most was finding the right way to show her.

This trip to Maui was her dream vacation. She had always talked about how much she loved Hawaii, and he wanted her to remember this trip forever — not just as a beautiful getaway, but as the beginning of a new chapter in their love story.

THE PLAN:

When we asked what he envisioned for his proposal, his answer was clear: something intimate, romantic, and unforgettable. He didn’t just want to ask a question; he wanted to create an big and romantic gesture that matched the love they had built over the past decade.

His vision was set: a beachside proposal at sunset, surrounded by flowers, roses, and candlelight. He imagined a pathway lined with blooms, leading up to giant glowing “MARRY ME” letters. He wanted balloons and florals to crowd the space with beauty, and for the backdrop to include the scenery that makes Maui so iconic — the ocean, the sky, and the feeling of paradise. More than anything, he wanted her to look back on Hawaii for the rest of their lives and think of this exact moment.

That’s where we came in. At Engaged on Maui, our team brought his vision to life with meticulous planning, design, and photography to make sure not a single detail was missed.

THE PROPOSAL:

The White Orchid Beach House in Maui was the perfect canvas for this love story. As the evening sky painted itself in shades of cool blue, she walked along a flower petal pathway that wound its way to the oceanfront. Each step was covered in flower petals and lined with white and pink florals.

At the end of the path, the grand “MARRY ME” letters stood tall against the backdrop of the Pacific. Blooms filled the space, creating a romantic, dreamlike setting that felt straight out of a movie.

There, surrounded by the sights and sounds of Maui, he dropped to one knee and asked the question he had been carrying in his heart for years. With the waves crashing gently behind them and the sunset painting the sky, she said yes.

Why Maui Proposals Are So Special

There’s something magical about Maui proposals. It’s not just the setting (though the island’s beaches, sunsets, and ocean views are unmatched); it’s the way the moment is elevated when paired with a place that already feels like paradise. For this couple, Maui will forever be more than a dream vacation spot. It will always be the place where a childhood love story turned into a lifelong promise.

At Engaged on Maui, we specialize in turning dream proposals into reality. From scouting breathtaking locations to designing romantic setups. To capturing every tear, laugh, and smile, we’re here to make sure your proposal is unforgettable.

Because the truth is, moments like these only happen once. And when you’re ready to ask the biggest question of your life, you deserve a team that knows how to bring the magic.

Want to see other proposal ideas and packages we offer? Check them out here!

If you loved this proposal, you’re also going to like these!

Justin and Allie’s proposal at a private cliff-side venue in Maui
Yumin and Jenfi at a private North Shore Maui Jungle Venue
Mark and Alex’s gorgeous beach proposal in Maui with florals

The post Romantic White Orchid Beach House Proposal | William and Roshni appeared first on Engaged on Maui | Maui Proposal Photographer.

Sumit and Jenny’s romantic proposal on Maui had hundreds of red roses and topped with a ‘Marry Me’ sign. We’re always excited to pull out these light up ‘Marry Me’ letters so when Sumit mentioned them we knew it was going to be stunning.

THE PLAN:

When Sumit reached out to us, he had a clear vision—he wanted his proposal to be romantic, unforgettable, and straight out of a dream. And let me tell you, he nailed it.

His plan? A secluded Maui beach, a rose-petal-lined walkway, and glowing “MARRY ME” letters as the perfect backdrop for one of the biggest moments of their lives. From the very start, you could feel how much thought and love he put into every detail. He wanted the setting to be just as breathtaking as the love they share. These high school sweethearts have been together for 10 years so he knew he wanted to go big!

THE PROPOSAL:

As the sun began to dip, casting that signature Maui golden glow, they arrived hand in hand. The sound of the waves, the roses lining the way, and the magic of the moment made time feel like it stood still. When Sumit dropped to one knee, emotions took over. And of course—Jenny said YES!

After celebrating, soaking in the moment, and capturing every happy tear, they shared a quiet, intimate walk along the shoreline. It was the kind of proposal that felt effortless, yet filled with so much meaning—a moment they’ll cherish forever.

To Sumit and Jenny: Thank you for choosing Engaged on Maui to plan and document your beautiful engagement and your romantic Maui proposal. Your proposal was one of our favorites from 2024!

Simple Proposal Package 

WANT A ROMANTIC PROPOSAL LIKE THIS ONE? CONTACT ENGAGED ON MAUI!

The post Romantic Maui Proposal | Sumit and Jenny | Wailea, Maui appeared first on Engaged on Maui | Maui Proposal Photographer.

Kris and Sophie’s romantic Maui beach proposal was a dream come true. Set against the backdrop of a breathtaking sunset and adorned with an abundance of vibrant red roses. As light danced on the waves, Kris knelt in the soft sand, asking Sophie to spend forever together. Kris and Sophie met in high school and have been together for 6 years. So this summer trip to Maui was the perfect time to pop the question!

THE PLAN:

Kris was super flexible in his proposal plans! He mentioned a beach proposal filled with roses. Simple and romantic, a perfect combo! So we picked the date that would work best for them while they visited Maui. After setting a date and time, I met them at one of our favorite beaches. At this point, all that was left to do was propose.

THE PROPOSAL:

Sophie was shocked as they walked in between rows of red roses and Kris got down on one knee. The evening was warm, inviting, and a perfect golden glow was wrapped around them. After the initial shock wore off, we took some photos with the red roses and let them walk along the shore for a mini engagement photoshoot. Then when the sun had set, we took out the flash and had some fun with the blue hue of the sky. But it was an absolutely perfect day for this very sweet couple. So the start of their forever begins!

Finally, Kris and Sophie: Thank you for choosing Engaged on Maui to plan and document your beautiful engagement and your romantic Maui beach proposal with was one I’ll remember forever! I’m wishing you nothing but happiness for your future!

Simple Proposal Package 

WANT A ROMANTIC PROPOSAL LIKE THIS ONE? CONTACT ENGAGED ON MAUI!

The post Romantic Maui Beach Proposal | Kris and Sophie | South Kihei appeared first on Engaged on Maui | Maui Proposal Photographer.

Bryce and Brianna’s love story found its perfect next chapter on the golden sands of Maui. Visiting the island for a dreamy getaway, Bryce knew he wanted to make their trip unforgettable by asking Brianna to spend forever with him. With the sound of gentle waves and the warm glow of a Maui sunset setting the stage, he planned a simple yet heartfelt beach proposal that was nothing short of magical. It was a moment filled with love, anticipation, and the beauty of Hawaii, creating memories they’ll treasure forever.

THE PLAN:

We had a lot of wiggle room when it came to this proposal. Bryce and Brianna had no big plans, so a romantic sunset proposal was easy. It was easy to pick from one of our favorite spots and set a meeting time just before the sun started to set.

THE PROPOSAL:

For the proposal, Bryce took Brianna to the designated beach while I hid behind some foliage. She was absolutely shocked that he got down on one knee and pulled out a wooden box with a ring. Brianna’s reaction was pure joy—a mix of surprise, happy tears, and laughter that made the moment feel even more special. After she said yes, it was time to capture their excitement in a series of candid and heartfelt photos. The Maui sunset creating the perfect romantic backdrop for their first moments as an engaged couple.

To Bryce and Brianna: Thank you for choosing us to spend this special moment with. It was an absolute honor to be a part of this magic. Your simple Maui beach proposal was one to remember forever!

Package: Simple Proposal Package

The post Simple Maui Beach Proposal appeared first on Engaged on Maui | Maui Proposal Photographer.

David and Shalene have a proposal story that spans over 35 years! David told us, “She and I met when we were freshmen in high school in 1987. I had a huge crush on her all four years of high school (so did everyone else, it seemed) but she had a boyfriend and we were in different social circles – she was in the popular, ‘cheerleader’ crowd and I was in more of the introverted, ‘nerdy’ crowd. She and I always got along though, and we bonded over music and other things. I even took notes for her in class, that’s how infatuated I was.

After high school we went our separate ways but reconnected on Facebook about 18 years later. We stayed in contact, but we were both in relationships so our communication was sporadic until we lost touch again. Another 13 years later (which would be last year), we reconnected again and this time the circumstances were right for us to be with each other. Though we currently live in different states, the chemistry was still there so we met in Vegas to go on our first date, a date I’ve waited about 35 years to take her on. The date was amazing and our relationship has been ever since.”

THE PLAN:

With a story that amazing, we knew David’s proposal needed to have a wow factor. A picnic proposal on the lawn at Wailea Beach Resort had the beautiful scenery and ambience he had in mind.

Our friends at Maui Luxe Picnics set up the picnic, complete with umbrella, pillows, and charcuterie board.

THE PROPOSAL:

The date marked one year from their first date. This made it easier to keep the proposal a surprise since Shalene didn’t question David planning something to celebrate their anniversary.

David made a personalized book of their love story, which was waiting at the picnic. Shalene flipped through the pages and when she got to the end, David dropped to one knee.

Scroll down to see the look on her face. You can tell how surprised and ecstatic she was! Our photographer Tenessa was able to get so many great photos of Shalene’s reaction to David’s proposal!

THE ENGAGEMENT SESSION:

David and Shalene enjoyed a bit of their picnic and some romantic photo time as the sun was setting. We were blessed with an incredible sunset that night that lingered and changed colors. Then Tenessa left our newly engaged couple to finish their picnic by light of the tiki torches.

David and Shalene: Thank you for letting us be part of your picnic proposal! This is just the beginning of your happily ever after!

Photographed by Associate Tenessa

Interested in a romantic picnic proposal?  Contact Engaged on Maui to get started on planning!

The post Picnic Proposal at Wailea Beach Resort | David + Shalene appeared first on Engaged on Maui | Maui Proposal Photographer.

When we heard about Cheryl’s background, we knew she was going to be crazy about Dante’s proposal!  Cheryl is an awesome Meteorologist in Chicago.  (She has quite an Instagram following, so she’s worth checking out HERE.  And HERE is her ABC 7 Eyewitness News Bio to check out!) Dante really wanted to have an above the clouds proposal in Maui because she’s a meteorologist and you know how they get about clouds and the sky and weather and all that good stuff.  That’s kind of her jam. So, to the top of Haleakala we went!

We could sit here and tell you all about how it happened…but who better to tell the story than Dante himself!

—–

“Slow down! You’re going to drive off the road!”

Cheryl was a ball of anxiety, sitting in the passenger seat; no, clinging to the armrest in the passenger seat of the white Jeep Wrangler she and her boyfriend, Dante, had rented for their stay in Maui.

They were on their way to the peak of Mount Haleakala, a dormant volcano on the east side of the island. Ascending it was no easy task. Even by four-wheel drive, and perfect weather conditions. Plus, Dante had something special planned set to coincide with the remarkable sunsets on the Mount that they couldn’t be late for. A plan a year in the works to propose to the love of his life, Cheryl.

Let’s back up a bit…

10 months earlier, in October, Cheryl and Dante set their sites on visiting Hawaii in December. Neither had been, but both knew very well of its enchanting landscapes. Dante decided this would be the place, and time, to pop the question.

He actually decided to propose about 2 years earlier, when Cheryl had taken him on a magical Ferris Wheel ride followed by a not so magical ride on the swings at Navy Pier in Chicago. Where the two live.

But now he had a set date and place he could start planning for. Nothing would get in his way!

He began seeking out places and people to make the occasion special.

Through some amazing friends in the event planning business he was referred to Engaged on Maui- a one stop shop for planning and capturing the special moment.

He spoke directly with Fawn and coordinated a breathtaking proposal for Haleakala National Park summit during sunset on the third night of their trip.

The heat was on and the clock was officially counting down. All they needed to do was get to Hawaii in December.

About ten days before their trip Cheryl came to Dante with some unsettling news.

“It looks like Hawaii is in the path of a tropical storm.”

She would know – she’s a meteorologist!

Cheryl, being one of the country’s top meteorologist’s tended to know these kinds of things.

“You have got to be kidding me.” (or something like that) Dante replied. Praying deep down the weather would cooperate.

It would not however, and the couple was forced to audible their plans the week of the Hawaii trip due to the torrent storm and instead go to Costa Rica.

Dante had no knowledge of Costa Rica, or contacts, so he went back and forth on popping the question there. Ultimately, he decided against it, and waited until the couple could reschedule for Hawaii.

One of the first memories Dante had of discussing marriage with Cheryl was her emphasizing how important the proposal was to her. She is very low maintenance and easy-going, but she made it clear her proposal needed to be special. Which was music to Dante’s ears, as he loves to go over the top on just about everything.

So just winging it in Costa Rica was out of the question.

Dante urged Cheryl to rebook Hawaii asap. They settled on early July of that year, 2018.

For the next six months Dante had to continue to hide the engagement ring from Cheryl and try to not over-think his plan.

Fawn was amazing at rescheduling and coordinating everything with Dante. The two of them figured out that Sunday night, July 8^th, would be ideal for the proposal. Fewer people on the mountain, and Dante was able to score a hard to get reservation at Mama’s Fish House so they could celebrate there afterwards.

Fawn ran a couple of her best photographers and videographers by Dante for approval. After seeing their past work he quickly agreed. Together, they planned out a perfectly timed sunset arrival for Dante and Cheryl at the parking lot just before the summit, which would provide the best chance at privacy. Engaged on Maui’s photographer and videographer would be setup there already, disguised as tourists taking in the sights off to the backside of the landing.

The plan was foolproof!

Or so they thought.

After arriving on Maui, taking in the local customs, scenery, and wildlife for a few days, Sunday was approaching. Dante had reached out to Cheryl’s oldest brother, Kevin, for approval and was given the green light. At the time, he thought he was more nervous about asking him than he would be asking Cheryl. (He was wrong).

On Saturday Dante and Fawn covertly spoke on the phone without Cheryl knowing and went over the final plan for the 100^th, and hopefully last time. They both checked the weather that night and things looked to be shaping up to be another beautiful day.

Sunday morning arrived and the weather was gorgeous as it had been all week.

The couple started the day with a nice walk along the shoreline before breakfast with plans to hit the beach for a few hours before trekking up to “explore” Mount Haleakala around sunset. Dante recalls not being able to believe the day had finally come as they lay on the beach late morning through lunch. Around lunchtime Dante checked his phone and nearly had a heart attack.

Weather can sometimes be finicky on Haleakala

There was a text from Fawn telling him to check his weather apps and the National Park’s website because it looked like a bad storm was moving in on the volcano summit.

Cheryl was just as excited as Dante to make the trek up to the summit, not knowing what was in store for her. But she became perturbed when Dante began asking her for weather updates relating to the mountaintop every 10 or 15 minutes.

“Why do you keep asking about the weather up there?”

“Just look at the clouds all moving in over there, you can tell without a radar it’s going to be bad up there.”

“We don’t have to go tonight, let’s just go later in the week.”

Dante thought to himself this couldn’t be happening again. The weather!

For the next 5 hours Dante and Fawn snuck phone calls, texts, and group emails with the photographer and videographer trying to decide whether to chance it and stick to that evening, or move it once again.

We had to reschedule.

The only night the photographer and videographer were available was the following night, Monday. They decided to roll the dice and plan for the next day as Dante sweated bullets through what was supposed to be the happiest celebratory dinner the couple ever had at Mama’s Fish House.

That night while laying in bed Dante refreshed the webcam stationed on Mount Haleakala hoping for a sign of good weather the next day. Cheryl continued to question why he was so concerned with the weather all of a sudden.

Monday came and with it brought beautiful weather once again. But Dante was weary.

He remained nervous the entire day.

Which may have explained his led-foot in the Jeep racing up the winding two lane “highway” to Haleakala’s peak.

The turbulent car ride did not please Cheryl. But they couldn’t be late and miss the sunset.

Upon finally arriving (safely) at the lookout spot Dante was relieved to see that Cheryl and he were the only people there. Aside from two “tourists” with professional photo equipment off by themselves taking in the majestic backdrop.

Breathtaking doesn’t do justice to the view from above the clouds with the sun making it’s slow departure, dipping behind them, casting a kaleidoscope of pinks, oranges, and pastels as far as the eye could see. This was definitely the right spot to ask the girl of his dreams, who had been obsessed with weather since she was a little girl, to spend the rest of her life with him.

As the couple looked out over the chain of islands dotting the Pacific ocean, and Dante ran through his gameplan trying to muster up the courage he suddenly needed, they heard rocks crunch to their left.

As they looked over towards the parking lot, a Church van was pulling in. It parked, and out exited about 12 tourists from Japan. Not only were they not alone anymore, but they all had high-end cameras around their necks. Which to Dante meant having to figure out a way to find a private spot now, and quick, or to photoshop them out of the pictures and video after.

Luck shined on him though and the tour group had a feeling a proposal was about to take place. Apparently, it was evident to everybody on the mountain that evening except for Cheryl, as the tour group stayed to the back and as Dante descended to one knee the photographer and videographer scrambled into place while recording.

Cheryl had no idea what was happening and in a confused state, just said “no” as Dante began to talk. Dante was caught off guard so stopped, to which Cheryl then told him “no go on.”

He began again, mind blacked out with emotion.

She said yes!

She said yes to spending the rest of her life with him and making him the happiest man in the world.

Cheryl claimed she was totally, absolutely surprised, but by the looks of Dante’s face in the pictures it looks like he was more so.

And the pictures!

The pictures of the two, set against the backdrop of the Maui sunset from up above the clouds look surreal. A work of CGI.

In the end, the weather cooperated, the meteorologist got her special proposal, the luckiest guy in the world got the girl of his dreams and Engaged on Maui captured it all perfectly on video and in photos. I couldn’t be happier!

Dante and Cheryl: Congratulations on your above the clouds proposal in Maui!  What an incredible sky we had up there that day! It’s like it was made just for you two!  Wishing you two all the best.

Photos by Associate Jess | Storyteller Proposal Package | Video by Areca Film Company

Want to propose above the clouds while on Maui?  We can help you with that! Contact Engaged on Maui today to get your plans in motion for the perfect proposal and photographs of your big day!

The post Above the Clouds Proposal in Maui | Dante + Cheryl appeared first on Engaged on Maui | Maui Proposal Photographer.