Hawaii Destination Wedding in Maui, HI

When I asked Jonathan and Ashley what they wanted their Maui Olowalu Plantation House wedding to look and feel like, they said, “natural, simple, and intimate”. What they did not mention was that all of their friends are fashion icons, talented dancers, and some of the warmest people I’ve ever met. Most destination weddings are smaller in size, but of course, Ashley and Jonathan’s family and close friends, who essentially are their adopted families, couldn’t miss out on their fun. Planning a destination wedding is no easy task, and the two were organized with their impressive spreadsheets, shuttle services for their guests, and delegated tasks. 

I’ve known Jonathan since our early days in our Deloitte management consulting internships. I remember him to be ambitious and curious.  I distinctly remember our conversations while hanging out with my college friends on a North Shore Boston beach. He was always so fun to be around! When I met Ashley, it was as if I couldn’t pick a better partner for him. She’s thoughtful in ways that I can only wish I be. She wanted to make sure all of her guests felt welcome as they walked into their Olowalu Plantation House wedding. She encouraged her bridesmaids to keep an eye out to make sure no one was alone, and if they were, to introduce them to someone with something in common so that they could strike up conversation. Prior to the wedding, I learned that Ashley had moved from SF to the suburbs to take care of her brother’s elderly dog when he moved to Hawaii because the dog was too old to travel. These are just two of the many things that stuck out to me about Ashley’s compassion.

Ashley and Jonathan are amazing at the little things. Ashley wanted her 3 year old and 1.5 year old nephews to be part of the celebration because they were important to her. She wanted her sister-in-law/wedding planner to have an amazing time and to not work. Jonathan wanted a dance floor because dancing was something he enjoyed so much, and he knew his friends would value good music and an awesome party, too! Jonathan would always be the first one to run up ahead to take care of things. Though all of his friends enjoyed roasting him and making fun of him during the wedding toasts, I think they would all agree that Jonathan is incredibly caring and very sweet. 

The two challenge once another in the best of ways, but you could see the warmth and support they had for each other… especially when I had them rock climb all over cliffs for their pre-wedding portrait session! 🙂 

Their wedding had so many little touches that they personalized. One of my favorites was their wine. For a 1 year anniversary present, Jonathan and Ashley made a barrel of wine in Napa and called it Three Pups Winery. It was meant to be served at their wedding 2 years later.

Ashley and Jonathan, you two are amazing people. There’s no doubt in my mind that you two are a perfect fit for one another and I can’t wait to hear of your future adventures together.  Thank you for taking care of so much for us… like dinner. We are so touched that you two reserved us seats at your table, and you’re right – we should’ve looked at your seating chart. 😉 Thank you for being two of the kindest bride and groom that Jason and I have had the pleasure of photographing. Please come visit us in Boston soon. <3 

Wedding planner: Kendall of White Orchid Wedding
Groom’s suit: Charlie Chang 
Florist: Teresa Sena
Band: Maui DJ Services 
Caterer: Cafe Olei 
Transportation service: Maui Tours and Transportation
Cake: Maui Wedding Cakes <mauiweddingcake@icloud.com>
Makeup and hair:  Christina Chen (maQeup@gmail.com) and Maui Makeup Artistry (mauimakeupartistry@icloud.com)

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