How to Propose in Maui

Featured Maui Proposal Tips
  • Choose a special location to pop the question in Maui
  • Practice getting down on one knee beforehand
  • Think about what you will say
  • Make reservations so you have a reason to dress up
  • Hire a proposal photographer to plan and capture the moment

Since 2013, Flytographer has captured thousands of surprise proposal photos all around the globe. Explore romantic proposal ideas and tips from real couples, including their top proposal ideas and tips, and the best ways and the best places to propose in Maui. Explore our customers’ heartwarming Maui proposal stories below.

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Gregory's Proposal Story in Maui

What is your love story?

We met through a mutual friend in DC when Gregory came back to his alma mater for homecoming. At the time, Gregory was living in Oakland, CA and Cha’koya was living in DC. Within a month of first meeting, Gregory was on a plane back to DC to come visit her. We love to travel. Our first real date was a trip to Seattle for Valentine’s day! At dinner one night in Seattle, Gregory looked over at her and said, “I can picture us and a couple of kiddos.” After two years of being long distance, Gregory moved across the country to join Cha’koya in DC.

What made you choose this proposal destination?

Maui has always been on the top of my list in terms of travel. Once I saw Baldwin Beach while doing research on the island, then I knew this was the place. The beach provides a variety of shots other than the water and my fiancé had never seen waves large enough to surf.

What is your proposal story?

During the initial photoshoot, I had the ring box in my back pocket and had to mange keeping my body facing forward so that my curious fiancé wouldn’t start asking questions. I can remember a few instances when I had to grab her hand so that she wouldn’t graze the ring box just below my lower back. Once we had taken a few shots by the lifeguard stand and on the edge of the beach, Rojeena signaled to me that the lighting was perfect. As the waves receded back into the ocean I grabbed my fiancé‘s hand and told her “You already know what this is.” Immediately, she was overwhelmed with emotion and I told her how much she had already impacted my life and how much I was looking forward to advancing our relationship for years to come. Our relationship started more than 3,000 miles apart, she lived in DC while I was in San Francisco. Now just over two years later, we are officially engaged and finally in the same time zone to start our next chapter.

Proposed in Maui in January

Photo Shoot Location: Baldwin Beach (North Shore)

Rojeena in Maui for Flytographer


Amar's Proposal Story in Maui

What is your love story?

Michelle and I met in college when we were actually competitive ballroom dance partners. While we were very close friends at the time, we actually did not start dating until about 5 years later at the end of medical school. Our journey fortunately took us both to Cincinnati for our residency training. Our relationship has been an incredible story of two cultures intertwining and a genuine friendship blossoming.

What made you choose this proposal destination?

I knew I was traveling out West to California but wanted to surprise Michelle with something truly spectacular. After seeing some of the sample photo galleries of the photographers in Maui, I was convinced that was where I wanted to propose!

What is your proposal story?

The entire trip to Maui was actually a surprise for my fiancé. We were out in the Bay Area for a work conference and the plan was to stay out West for a few extra days after the conference. I told Michelle that we were going to LA for four days, but as we were checking into the kiosk at the airport, I told her I had a secret for her and the tickets to Maui popped up on the screen at that moment. I proposed to her later that night after we arrived in Maui after our Flytographer concierge and photographer suggested Po'olenalena Beach for the location. It was a quiet, "locals" beach that was very intimate. I proposed around sunset and she said YES! We could not be happier with how things went.

Proposed in Maui in September

Photo Shoot Location: Po’olenalena Beach (South Shore)

Taena in Maui for Flytographer


Caleb's Proposal Story in Maui

What is your love story?

I met Kennedy through her older sister who was dating my best friend at the time. It wasnt’t until 8 years later Kennedy and I had started dating.

What made you choose this proposal destination?

You can’t go wrong with Maui! It’s hard to mess up a proposal there! Also, the views are unbeatable and we both love everything about Maui.

What is your proposal story?

My family and I had planned to go to a nice restaurant an hour and a half early (she thought we were on time for dinner) so I could take Kennedy down to the beach and play guitar for her. When we got to the restaurant my dad faked that he had gone to the hostess to check in. He came back to the group and told us it was going to be a while so my mom suggested I take my guitar down to the beach and play for a while. Kennedy insisted she had to go to the restroom inside the restaurant which was right next to the bar that her parents, who were supposed to surprise her, were hiding at. We went inside and I shielded her from seeing the bar area where her parents were. After we were done with the restrooms we made it down to the beach area. I set up my guitar and started playing for her. I played a couple songs we both love to sing together and then it was time. I stood her up and told her, “I know we’ve been talking about doing this for a while.” At that moment she knew exactly what was going on, as she covered her mouth with her hand in shock. I could only muster a few more words until I started to tear up. So I got down on one knee and said, “Kennedy Renae Shields will you marry me?” Without hesitation, she said yes! I was so happy to finally have proposed because it was 6 days into our trip and and the anticipation was killing me the entire vacation. I put the ring on her finger, stood up, and hugged her. Little did she know her parents were right behind her ready to surprise her. When she saw her parents she couldn’t believe it and said, “could this be any more perfect?” All in all the proposal went just as planned and I couldn’t be happier with the outcome of everything.

Proposed in Maui in March

Photo Shoot Location: Custom Route

Amity in Maui for Flytographer


Vito's Proposal Story in Maui

What is your love story?

10 years ago, my girlfriend and I met when we were in high school. We both were competitive swimmers and swam on the same team. We stayed very close friends even as I continued studies in Victoria, BC, and she got a scholarship to school in Texas. We both had feelings for each other but were chickens to say anything because we didn't want to ruin/lose the friendship if the other person didn't feel the same way. It wasn't until 5 years later, that we planned and booked a 3 week backpacking trip across Japan! This was a trip that no family or friend believed would actually happen. But, Natalie and I both loved to travel and so we began our 513 day countdown. This trip was life-changing and was were our friendship grew into love. I knew she was the one for me because she always made my heart smile. She has the most beautiful, compassionate, giving, and loving heart I know. She supports me through life, no matter what. I love her with all my heart, but she is also my best friend. I can't wait to spend the rest of my life with her.

What made you choose this proposal destination?

Maui is beautiful. My girlfriend loves sunsets and the beach. Maui offered me the opportunity for a romantic and unforgettable proposal destination.

What is your proposal story?

The proposal went perfectly. With the help of my shoot concierge, and especially my photographer Marie, we were able to plan the perfect proposal. My girlfriend had originally booked this photo shoot as a memory for this trip to Maui. We were celebrating out 5 years together as well as my 25th birthday. I knew Maui was the perfect place to propose, so I contacted Marie in secret to plan this day. I wanted the beginning of the shoot to go as planned, just regular photos by the beach. I wanted my girlfriend to have no idea this proposal was happening. Marie thought of doing half the photo shoot on one beach, then drive down he street to another. Marie, the shoot concierge, and I planned cues for the special day. The day finally came, and when we were at the second beach, Marie asked my girlfriend to take some single shots of her looking towards the ocean/sunset. This was my cue to sneak behind her and get on my knee. I called my girlfriends name from behind and she turned around and was so happy and surprised! I am so grateful for how the proposal went, and the beautiful photos we both have to forever remember this special moment.

Proposed in Maui in October

Photo Shoot Location: Po’olenalena Beach (South Shore)

Marie in Maui for Flytographer


Michael's Proposal Story in Maui

What is your love story?

Ana and I met at a bar after I moved to Houston, TX for work. Ana was funny, kind and loved dogs just as much as I do (we now own the most amazing Golden Retriever)

What made you choose this proposal destination?

Hawaii is the most beautiful place in the world and I knew Ana wanted a beach proposal. There was just no better place!

What is your proposal story?

I told Ana we were going on a boat (which would leave from the beach) to explore some coves and caves. After my masterful trick worked, I proposed!

Proposed in Maui in May

Photo Shoot Location: Custom Route

Rojeena in Maui for Flytographer


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