You know that pair of dating friends you have that travel to Hawai’i every year & you hope to whatever God above they’ll get engaged so you have an excuse to get fancy in the islands? Me neither.

Oh, how we would have all benefited from being friends with Caitlyn & Ryan!

When the high school sweethearts – who’d been together for a decade – got engaged on Maui, it was assumed by all that the newly engaged would be whisking their closest friends & family members away to the tropical islands – and oh, did they deliver!

Using their decade of Hawaiian intel & the oh-so-sought-after local planner Maui’s Angels, the couple incorporated all the best of Maui at their Olowalu Plantation wedding day. Photographed in a fitting creamy, dreamy style by Rebecca Arthurs, we’re dying for weddings in the Hawaiian Islands.

Our Love Story

We met over ten years ago when we were on summer break from high school. We didn’t know each other because we went to different schools but met randomly when hanging out with mutual friends. After we met, Ryan made a point to continue to hang out with those same mutual friends every day in the hopes of getting to know me better. Ryan finally asked me out on our first date, but the funny part was that he was only 16 and didn’t have a driver’s license yet, so since I’m a year older, I had to pick him up! He asked me to be his girlfriend a few weeks later, and we have been together ever since!

We have such an abundance of unforgettable memories together. Although I think we are still just like those “young and in love” teenagers, we have grown up so much over the years. We have gotten to experience being high school sweethearts and going to prom together, working our first minimum wage job together, graduating college together, and watching each other start real adult jobs. We would not be where we are today without each other’s help.

The Proposal

We were on vacation in Maui, and I had heard of this place called Haiku Mill, one of Hawaii’s most beautiful wedding venues. I figured we should go on a botanical tour of the mill while on Maui. Ryan thought it was a great idea and said he would set it up. In reality, he had already blocked off all the tours for that day to pull off a surprise proposal!

Our guide led us around the breathtaking property until we got to the ruins of the historic mill. Ryan held my hand as we walked through the doorway until we stopped under a crystal chandelier surrounded by beautiful cascading flowers. I was looking around in awe when he took both my hands and said, “I have to let you in on a little secret. We are not here for a tour”. I immediately knew what was happening but couldn’t believe it. The next thing I knew, Ryan was kneeling and asking me to marry him. It was the happiest moment of our lives!

The Dress & Attire

I found my wedding dress in NYC at the Lovely Bride. I had tried on a handful of gowns, but I didn’t get THE feeling until I tried on the Sierra gown by Limor Rosen! I worked with the designer to make some minor alterations to the dress; it was my dream gown! It is a delicate fitted gown with beautiful beaded lace, a deep V-neck top, and a unique lace train.

I allowed my bridesmaids to each pick their unique dress from Azazie. I wanted them to feel comfortable and like themselves! MeiLi Autumn Beauty did our hair & makeup. I allowed the girls to pick any hairstyle they wanted and had all of us wear flowers in our hair.

The groom and groomsmen wore custom blue suits from Indochino with an open collar and no tie. The men’s blue suits reminded us of the color of the Pacific Ocean, while the women’s dusty rose dresses gave a subtle pop of color against the tropical green landscape.

The Destination

When we got engaged, it was assumed by all our friends and family that our wedding would be in Hawaii. We have traveled there at least once a year since we started dating over ten years ago. We often considered the Hawaiian Islands our second home and feel they are where we truly fell in love. We chose Maui due to our history of getting engaged there, its obvious beauty, diverse landscape, ease of navigating, and abundance of excellent wedding vendors.

The Venue

We picked the Olowalu Plantation House due to its private oceanfront location, history, lush tropical landscape, and flexible design space. The plantation house was the bridal suite and a beautiful room to get ready. The grounds served as a blank slate, allowing us to design designated areas for the ceremony, cocktail hour, lawn games, lounge, and reception with the ocean as our backdrop.

The Photography

Since we were having a destination wedding, picking an excellent photographer and videographer was essential so we could share the day with anyone unable to make it to our wedding in Hawaii.

Our photographer was the first vendor we picked. We browsed Pinterest for Maui weddings and found one Rebecca Arthurs captured and immediately fell in love. We went to her portfolio, and that was it; we knew she was the one! We loved her soft, romantic, and authentic shooting style. Her photos looked dreamy and never posed or forced, which was essential to us. We also loved that she shot both digitally and with vintage film! When we look through our photos, we are brought back to each moment and can’t believe such stunning photos are ours!

The Videography

We watched SO many videos for our videographer, and those by Ohana Films were by far the best! Their videos looked like movie quality, from their music and editing choices to their use of drone footage. They could capture each moment of the day and the raw emotions that came with them. They stayed in the background and didn’t have us “recreate” moments and instead filmed them as they happened naturally. The final product is stunning; we will cherish it for the rest of our lives!