A Perfect Match: Jenna & Joseph’s Sundial Wedding Story
We had the honor of catching up with Jenna, a recent bride who celebrated her wedding at Sundial, to hear all about her special day and glean some insights for future couples. Her enthusiasm for her experience was infectious, and we’re thrilled to share her story!
How did you meet?
Joseph and I met like many modern couples do these days—we matched on Tinder back in 2018. Our first date was to a pizza place in Lexington, Kentucky, and it ended up lasting about six hours! Not exactly by choice, as our waitress disappeared, but luckily, we found it incredibly easy to talk to each other. What could have been an awkward situation turned into a really memorable first date.
Describe the proposal.
When a work opportunity brought me to Hawaii, Joseph knew it was the perfect place to celebrate our five-year anniversary and, as it turned out, to propose. He bought the ring without anyone knowing, while I, on the other hand, was convinced he wouldn’t propose in such a “cliché” setting. He carried that ring from island to island, finally finding the perfect spot: 9,200 feet up on the dormant volcano Mauna Kea, during the most incredible sunset we had ever seen.
When we stopped to take pictures, I wanted a couple’s photo and started setting up a countdown timer. Meanwhile, Joseph was getting ready for his big moment. Seeing me get frustrated with the temperature dropping to 40 degrees, Joseph suggested we take a video instead and pull stills later—a comment that completely went over my head! I just ran back to the car, unknowingly messing up my own perfect proposal.
Not wanting me to get too cold, or himself to get cold feet, Joseph decided to try again the next day at Volcanoes National Park. So, on October 26, 2023, on a rocky outcrop at Punalu’u Black Sands Beach, Joseph asked me to be his wife… Crocs and all!
What were some of your favorite details from your wedding?
It’s really tough to narrow them down because we truly loved every single detail about our day. But if I had to pick our top three, they would be:
Incorporating our pets: We have two amazing pets, and we found subtle ways to include them. Joseph’s cufflinks and socks featured them, and we even named our signature drinks after them—the “Sanibel Skye” and “Captiva Chase.” How perfect is it that their names are alliterative with the islands?!
Our song/sound choices: We had some fun with our music! Our parents walked in to “The Price is Right” theme song. My dad watches the show religiously and even attended a taping once but didn’t make it on stage, so I saw this as a chance to finally give my parents their “Come on Down!” moment! We also ended the night with “Hot to Go”—it was so fitting given how warm it was that day, even though we’d picked the song weeks earlier.
Girlhood/Boyhood moments: We deeply value our support systems and wanted to honor them. Joseph had a “boys” picture taken with all the male family members from both sides, and I did the same with all the female members. I also had a special “princess moment” where I invited all the girls (and girls at heart!) in the room to dance to “Miracles Happen” from The Princess Diaries.
Why did you choose Sundial as your venue?
Initially, I was set on a spring wedding in Kentucky, but as I started planning, none of the venues there felt quite right. My family has a really special connection to Sanibel Island; my grandfather bought a timeshare there in the 1980s, and Joseph and I spent many vacations there. Unfortunately, like much of the island, our timeshare was devastated by Hurricane Ian.
Then, in December 2023, I randomly stumbled upon a Facebook post from Sundial advertising weddings. I immediately scheduled a tour and was on a plane within days to check it out. It was my first chance to visit the island post-hurricane, and even though it was still badly storm-damaged and full of debris, I completely fell in love with the charm and potential of the venue. The scenery pretty much sells itself, but our venue contact really sealed the deal. They patiently answered my endless list of questions and even spent an hour shelling with me at sunset. Plus, getting the chance to bring some much-needed revenue to an island we love so much felt like a gift that kept on giving from our guests.
Would you recommend Sundial to other couples?
Absolutely—I cannot say enough great things about Sundial! The accommodations are stunning, the food is amazing, and the convenient amenities, combined with their partially inclusive wedding packages, made planning so much easier. But what truly set them apart was the incredible hospitality. The team was always quick to respond, handled every challenge with such care, and made the whole process feel incredibly easy and enjoyable. One staff member even connected with us so deeply that he gifted us a hand-drawn piece of art, which is now our most treasured wedding gift.
What advice would you give to future couples?
My biggest piece of advice is to trust your gut. If the vibes feel off during initial conversations, they will likely be off on your special day too. You’re going to be overwhelmed by choices—it’s just part of the process! When that happens, focus on value, not just cost. The cheapest option isn’t always the best, and a high price certainly doesn’t guarantee quality. Also, don’t feel the need to keep up with every trend. Your wedding is a time to perfectly portray the nuances of your relationship, not to go viral on TikTok for the next best wedding idea.
Thank you, Jenna, for sharing the story of your relationship and your beautiful wedding! Are you ready to start planning your dream day? Contact Sundial’s team of Wedding Experts today and let’s begin!
Photography provided by Taylor Shea Photo
