Mountain to Ocean Engagement

Sometimes, the third time is the charm.  It definitely was for Cyprian’s proposal to Charlene!  Maui’s weather can be unpredictable. Since Maui has so many micro-climates, we can generally find a spot with the perfect weather for a proposal–even if it’s our third try!  For Cyprian and Charlene’s mountain to ocean engagement session we traversed the island! This couple’s energy was contagious and they were up for anything!


Cyprian really wanted to propose on top of Haleakala, but we were in the middle of 5 days of straight rain, which is pretty much unheard of on Maui!  We had to be flexible with the proposal location and timing because of this crazy weather.  Luckily, Cyprian was ready to go with the flow!  For the first attempt, it was pouring down rain at the summit, so we scrapped that plan and said we’d try again another day that week.  We tried again the second day to go to the summit, but it was raining–again!  The third plan was Cyprian would follow me down until we found a place where it wasn’t raining and we’d stop there so he could FINALLY propose.


We got halfway down the mountain and found a parting in the clouds. I pulled off to the side of the road and Cyprian followed suit.  We came up to this beautiful wide open field, I parked and pretended to be a tourist taking photos.  He led Charlene to the edge of the cliff where we were able to see all of Maui down below. That’s where he asked her to marry him! Of course, she said YES!


We spent a little time taking photos in the field and then we headed back down the mountain to find some sunshine! On the way down, we stopped by one of my favorite coffee shops, Sip Me in Makawao.  There we got some cozy shots along with our coffee.  Cyprian’s sister, who does calligraphy, made some cute signs for them, and we were able to get some photos with those, too!  Because we were chasing the sun and weren’t having any luck upcountry, we decided to do a mountain to ocean engagement session and drove to Baldwin Beach in Paia.  There we had gorgeous views of the West Maui Mountains, and we had the beach all to ourselves!  What an adventurous day!

side of road with hills of Haleakala looking down on the Pacific rolling hills on the way down Haleakala Road and hillside of Haleakala couple walking down happy couple standing overlooking the valley in Maui couple standing on cliffside of Haleakala about to propose first moments of man proposing to girlfriend man proposing down on one knee with Maui's valley beneath them man down on one knee proposing couple just after proposal on the side of Haleakala overlooking Maui woman and man smiling holding both hands on Haleakala princess cut engagement ring on hand couple canoodling over coffee hands holding coffees princess cut diamond engagmenet ring in dew covered greenery man and woman holding signs kissing and drinking coffee couple in love hugging new fiances holding hands and walking down a sandy path through the woods couple holding hands walking through the plants couple hugging on a hike new fiances running towards the Maui ocean fiances snuggling and piggy back riding through the waves man carrying fiance on his back in the waves black and white photo couple walking on beach couple sitting under trees on Maui beach newly engaged couple hugging on beach couple standing on sand with engagement date etched into sand Maui couple excited to see engagement ring

Cyprian and Charlene, you were a joy to photograph!  Thank you so much for letting Engaged on Maui be a part of your mountain to ocean engagement!  I loved traversing the island with you both.

Photos by Angie | Perfect Proposal Package 

Are you looking for a surprise engagement shoot on a mountain, near the ocean, or a little of both?

Contact me here and we can make a plan!

Similar Posts