Destination Weddings/Real Weddings

High School Sweethearts’ Dream Hawaiian Wedding

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

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 to come on in the Hawaiian Islands.

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

Our Love Story

We met over 10 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, 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! A few weeks later he asked me to be his girlfriend and we have been together ever since!

We have such an abundance of amazing memories together. Although I like to think we are still just like those “young and in love” teenagers, we have both 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 both not be where we are today without each other’s help.

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

The Proposal

We were on vacation on Maui and I had heard of this place called Haiku Mill that was known as one of the most beautiful wedding venues in all of Hawaii. I figured while on Maui, we should go on a botanical tour of the mill. Ryan thought it was a great idea and told me he would set it up. In reality, he had already blocked off all of the tours for that day so he could 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. Next thing I knew, Ryan was down on one knee and asking me to marry him. It was the happiest moment of our lives! 

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

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 and it was truly my dream gown! It is a delicate fitted gown made with beautiful beaded lace, a deep V-neck top, and a unique lace train.

I allowed my bridesmaids to each pick their own 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.

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

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 10 years ago. We often considered the Hawaiian Islands our second home and feel they are where we truly fell in love. We choose Maui due to our history getting engaged there, its obvious beauty, diverse landscape, ease of navigating, and abundance of wonderful wedding vendors.

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

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 itself served as the bridal suite and a beautiful space to get ready in. 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.

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

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 who was unable to make it our wedding in Hawaii.

Our photographer was the first vendor we picked. We browsed Pinterest for Maui weddings and came across one captured by Rebecca Arthurs 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 so dreamy and never looked posed or forced which was important 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!

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

The Videography

For our videographer, we watched SO many videos 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 were able to 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 and we will cherish it for the rest of our lives!

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

The Drinks & Dinner

We hired a local specialty bar provider from Maui, Garnish Cocktails. Garnish was incredibly unique in that they work with all local farms and vendors to source the ingredients for our cocktails. We choose our own signature drinks with had unique island twists such as a sea salt infusion and local fruits!

For our reception, we opted for food stations that stayed open throughout the night rather than a plated dinner. We wanted it to feel like an elegant backyard wedding. People could dance, play lawn games, lounge, or eat at their leisure. For dinner, we wanted to cater to all food preferences and appetites so opted for various “small plates”, a poke station, slider station, and raw bar.

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

The Music

On one of our early trips to Hawaii, we had spent some time hanging out at a beach bar on Oahu. We had heard an amazing musician play and always reminisced on how talented he was. When we were planning our wedding, Ryan had called the beach bar and after talking to several people, found out the name and contact information for the artist, Jeremy Cheng. We got to know Jeremy throughout the planning process and were so happy he flew into Maui to play during our ceremony, cocktail hour and reception.

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

The Unique & Personal Details

It was important for us to include as many personalized details as possible. I pinned a photo of my paternal grandparents on my bouquet and Ryan pinned photos of his maternal grandparents inside his suit jacket as a way of having them with us that day.

Since we dated for 10 years before getting married, we wanted a way to showcase our history together so our wedding planner came up with an idea for a floating picture gallery to adorn the outdoor lounge area. It featured pictures from high school prom, to graduation, to our engagement. It was probably our favorite detail of the day! We also included a bookshelf showcasing loved ones who have passed on, our baby photos, our pets back home, and our parents’ and grandparents’ wedding photos.

For our seating chart, we wanted something unique that was never done before. Since we loved to island-hop in Hawaii, we had Miss B Calligraphy create a seating chart display featuring floating wooden cutouts of the Hawaiian islands with each island representing a different table!

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan
View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

Advice to Other Couples

If you’re having a destination wedding, hire a local wedding planner! They will know all of the local venders and be able to help you choose the best ones for your budget and style. Our wedding planner, Ali, was an absolute dream to work with. She took so much of the stress away from planning a destination wedding and made the entire process fun. She truly put together the wedding of our dreams and had every little detail planned to perfection.

Our biggest piece of advice on the big day would be to take a moment alone with your partner to step back and take it all in. After dinner, we held hands and walked around the grounds to admire all of the beautiful details and watch our guests having a great time. It was one of our favorite and most memorable moments of the night!

View More: https://rebeccaarthurs.pass.us/caitlyn-ryan

The Honeymoon

For our honeymoon, we were already on Maui so we decided to island hope to some of the other Hawaiian Islands. Our favorite stop on our honeymoon was on the little island of Lanai where we stayed at the breathtaking Four Seasons Resort. Aside from having one of the most beautiful resorts in all of Hawaii, we loved renting a Jeep and exploring the island where we found secluded beaches and ancient Hawaiian ruins.

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