Anna getting down on one knee to propose to Jessa at Air Maui's Oceanfront Landing

Oceanfront Helicopter Proposal in West Maui | Anna + Jessa

Oceanfront Helicopter Proposal

Anna contacted us last minute because she just happened to find the perfect ring. With their upcoming trip to Maui, it seemed like the ideal opportunity to pop the question to her love Jessa. An Oceanfront Helicopter Proposal gave them an amazing adventure and private proposal all in one!


When thinking about her proposal, Anna said, “I just want to give her a memorable, cinematic experience. She’s down to earth, but she’s also my princess. The helicopter appealed to me because it’s kind of over the top in a good way.”

With those words, Anna really summed what we love most about our Air Maui proposals. You’re not only getting engaged but having an amazing experience, seeing the beauty of the islands from the sky. Those memories will stay with you for a lifetime, and you’ll have the pictures to help you relive all those magical feelings.


Once we got to the landing, Anna led Jessa out towards the ocean. Jessa thought they were checking out the scenery and had no idea how her life was about to change in the next few moments. With the waves in the background and a palm tree beside them, Anna asked Jessa to marry her and Jessa happily said YES!!!


Anna and Jessa were both so overjoyed. Our time together at the landing really flew by (no pun intended), but we had such a blast. They couldn’t stop smiling and laughing. When we can get genuine smiles and pure emotion, it makes our job easy.

When they received their gallery, Anna and Jesse wrote to us and said, “Thank you again for your amazing work on our engagement! We are SO delighted with the full set of photos that we received today. More than that, we are deeply enjoying looking back on our special day that happened thanks to you two!”

Boarding the Air Maui helicopter before flight

Jessa and Anna looking out the window of the helicopter

View of Oceanfront Landing (West Maui/Molokai) tour

Waterfalls as seen from Air Maui Oceanfront Landing tour

Bird's eye view of Molokai on Air Maui tour

Rock formation shaped like an elephant located to the north of Molokai

Anna leading Jessa to the proposal location at Oceanfront Landing

Anna getting down on one knee to propose to Jessa at Air Maui's Oceanfront Landing

Oceanfront helicopter proposal

Closeup of Anna's romantic oceanfront helicopter proposal to Jessa

Anna getting Jessa's engagement ring out

Anna putting Jessa's engagement ring on

Jessa said Yes to oceanfront helicopter proposal

Embrace after Maui oceanfront helicopter proposal

Reaction to private oceanfront helicopter proposal and surprise photographer

Jessa is thrilled that Anna pulled off this surprise Maui proposal at Air Maui's oceanfront landing

Celebrating their oceanfront helicopter proposal

Engagement ring with blue stone

Happiness after Maui proposal at helicopter landing

Soaking in the moment

Posing on the rocky beach

Anna kissing Jessa on the cheek after proposal

Flying back on the helicopter after proposal

Anna and Jessa: Your love is beautiful and we couldn’t be more happy for you!

Photographed by Associate Samantha | Air Maui Charter Package

Interested in a Maui helicopter proposal for your love?  Fill out our inquiry form to start planning with Engaged on Maui!

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