Wedding Fullfrontal Wedding School Sweethearts Dream Hawaii Wedding

School Sweethearts Dream Hawaii Wedding

Do you know the couple of dating friends that you travel to Hawaii every year and you hope to get engaged to the God above you so that you have an excuse to have fun on the islands? Neither do I.

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

When the high school darlings – who had been together for a decade- got engaged in Maui, everyone assumed that the newly engaged would bring their closest friends and family members to the tropical islands – and oh, they delivered!

Thanks to their decades of Hawaiian knowledge and the highly sought-after local planners at Maui’s Angels, the couple recorded the best of Maui on their wedding day at Olowalu Plantation. Photographed in a creamy and dreamy style matched by Rebecca Arthurs, we aspire to weddings in the Hawaiian Islands.


We were on vacation in Maui and I had heard about this place called Haiku Mill, known as one of the most beautiful wedding venues in Hawaii. I thought that while we are in Maui, we should take a botanical tour of the mill. Ryan thought it was a good idea and told me he was going to set it up. In fact, he had already closed all the visits for that day so that he could make a surprise proposal!

Our Guide guided us around the magnificent property until we arrived at the ruins of the historic mill. Ryan held my hand as we walked out the door until we stopped under a crystal chandelier surrounded by beautiful flowers. I looked around with admiration when he took both my hands and said: “I have to tell you a little secret. We are not here for a tour.”I knew right away what was happening, but I couldn’t believe it. The next thing I knew was that Ryan was lying on one knee and asked me to marry him. It was the happiest moment of our life!

The Dress And The Clothes

I found my wedding dress in New York at the Lovely Bride. I had tried a handful of dresses, but I only felt this way when I tried the Sierra dress by Limor Rosen! I worked with the Designer to make some minor changes to the dress, and it really was my dream dress! It is a delicately fitted dress made of beautiful beaded lace, a deep V-neck top and a unique lace train.

I allowed my bridesmaids to each choose their own unique Azazie dress. I wanted you to feel comfortable and love each other! MeiLi Autumn Beauty did our hair and makeup. I allowed the girls to choose any hairstyle they wanted and let us wear all the flowers in our hair.

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


When we got engaged, all our friends and family assumed that our wedding would take place in Hawaii. We’ve been there at least once a year since we started dating over 10 years ago. We have often considered the Hawaiian Islands as our second home and we have the feeling that we have really fallen in love there. We chose Maui because we got engaged there, its obvious beauty, its varied landscapes, its ease of navigation and the abundance of wonderful wedding vendors.


We chose Olowalu Plantation House for its private beachfront location, history, lush tropical landscapes and flexible design space. The plantation house itself served as a bridal suite and a nice space to get ready. The land served as a blank sheet and allowed us to create designated areas for the ceremony, cocktail hour, lawn games, lounge and reception with the sea as a backdrop.


Since we had a wedding in a destination, it was important to choose an excellent photographer and videographer so that we could share the day with everyone who could not make it to our wedding in Hawaii.

Our photographer was the first seller we chose. We searched Pinterest for Maui weddings and came across one of Rebecca Arthur’s favorites and fell in love immediately. We went to her wallet and that’s it, we knew she was the one! We loved his gentle, romantic and authentic filming 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 a Vintage Film! Looking through our photos, we are brought back to every moment and cannot believe that such stunning photos belong to us!

The Videography

For our videographer, we saw so many videos and the ones from Ohana Films were by far the best! Their videos looked like quality movies, from the selection of music and editing to the use of drone equipment. They could capture every moment of the day and the associated emotions. They stayed in the background and didn’t let us “recreate” moments and filmed them instead as they happened naturally. The final product is breathtaking and we will enjoy it for the rest of our lives!

Drinks & Dinner

We hired a local Maui specialty bar vendor to top Cocktails. The topping was incredibly unique, as they work with all the local farms and suppliers to get the ingredients for our Cocktails. We choose our own Signature drinks with unique island twists like a sea salt infusion and local fruits!

For our reception, we opted for food stations that stay open all night rather than for a plated dinner. We wanted it to look like an elegant backyard wedding. People could dance, play lawn games, lounge or eat at will. For dinner, we wanted to satisfy all food preferences and desires, and so we opted for different “small plates”, a Poke station, a Slider station and a Raw bar.


On one of our first trips to Hawaii, we had spent time at a beach bar on Oahu. We had heard a great musician play and we always remembered his talent. When we planned our wedding, Ryan had called the beach bar and, after talking with several people, had discovered the name and contact details of the artist Jeremy Cheng. We met Jeremy throughout the planning process and we were so happy that he flew to Maui to play during our ceremony, cocktail lesson and reception.

Tips for other couples

If you have a wedding in your destination, hire a local wedding planner! They know all the local sellers and can help you choose the best one for your budget and style. Our wedding planner Ali was an absolute dream. She took so much stress out of planning a destination wedding and did the whole process for fun. She really put together the wedding of our dreams and planned every detail perfectly.

Our biggest tip on the big day would be to take a Moment alone with your partner to take a step back and pick everything up. After dinner, we held hands and walked around the place to admire all the beautiful details and watch our guests have a great time. It was one of our favorite and unforgettable moments of the night!


For our honeymoon, we were already in Maui, so we decided to take Island Hope to some of the other Hawaiian islands. Our favorite stop on our honeymoon was on the small island of Lanai, where we stayed at the beautiful Four Seasons Resort. In addition to having one of the most beautiful resorts In Hawaii, we loved renting a Jeep and exploring the island, where we found secluded beaches and ancient Hawaiian ruins.

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