Today’s blog is brought to you by an epic Maui family proposal. Read all about it below! 

Southside Beach Proposal with Awesome Family Surprise

Both sides of the family were involved in this heartfelt proposal! Giles’ mom helped with the planning and cover story. Not wanting to be left out, Kesslee’s mom and grandma came to surprise Kesslee after the proposal.

THE PLAN:

Since Giles and Kesslee were coming on vacation with Giles’ family, the cover story to get everyone to the beach dressed up on time was a family photoshoot.

Giles’ mom Natalie was our point of contact. When Natalie and family got to the beach, we called and told Natalie that their photographer was running late, so everyone could relax until she got there. This was Giles’ cue to walk Kesslee down the beach.

Meanwhile, our associate Amber already had the flower circle set up and was waiting on the beach. The flower circle was requested to make the plan as easy as possible for Giles. All he had to was look for the circle and make sure he faced Kesslee the right way.

Kesslee’s mom and grandma met us at the beach before everyone else arrived and we hid them away. Kesslee had no clue they would be there at all. Since her family being there would be a major shock, we thought it best to have them hiding during the proposal, in a spot where they could still watch the magic, but not distract from the big moment. Then we gave Kesslee a chance to take in the fact that she just got engaged before surprising her again!

THE PROPOSAL:

The plan went off wonderfully! Giles led Kesslee into the flower circle as both families looked on – his family down the beach and her family hiding in the trees. Kesslee was so thrilled! Little did she know, the proposal wasn’t the only surprise.

THE ENGAGEMENT SESSION:

Giles’ family came over to congratulate the happy couple and take some group photos. Then we stole Giles and Kesslee away. Amber told them to look towards the ocean. With their backs to the trees, it was the perfect opportunity for Kesslee’s mom and grandma to come out of hiding. Kesslee’s face went from disbelief to joy and happy tears! Seeing her family there too and realizing they had traveled so far to witness her engagement was icing on the cake!

Kesslee and Giles exchanged leis and danced together on the beach before joining back up with their families for a few more photos at sunset. Everyone made memories that evening to last a lifetime and they have the photos to keep those memories alive!

Congratulations Giles and Kesslee! Thank you for letting us capture your memorable Maui family proposal! We loved seeing your families come together and we wish you the most beautiful life together!

Photos by Associate Amber | Simple Proposal Package

Want to plan a surprise proposal but don’t know where to start?  Start by contacting Engaged on Maui so we can help!

Looking to stay inspired? Check out Shawn and Kim’s secluded beach proposal!