Jenna Lee Shares Hawaii Proposal Photo Advice

Men's Dating

Photographer Jenna Lee Shares Advice for Stunning Proposal and Engagement Photos in Hawaii

Sheena Holt

Written by: Sheena Holt

Sheena Holt

Sheena Holt comes to DatingAdvice with a BA in English and creative writing. Sheena's work has appeared in numerous literary and culture publications, including Lithium Magazine. Her work as an editor and writer has taught her a lot about the ins and outs of dating in the 21st century. As Managing Editor for, she has interviewed hundreds of dating professionals and relationship experts. Sheena also enjoys writing long-form fiction in her spare time to keep her storytelling skills sharp.

See full bio »

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

Discuss This! Discuss This!

The Short Version: Planning your wedding is exciting, and it comes with many important components. Starting with your engagement photos. We spoke with award-winning photographer Jenna Lee about her recommendations for couples looking to take proposal or engagement photos in Hawaii. She shared her insights, from the benefits of working with a professional photographer to what you can expect from the culture and terrain of each major Hawaiian island.

The months leading up to your wedding are filled with beautiful moments you’ll cherish throughout your relationship. Executing the proposal, planning the wedding, and preparing for your life with your partner as a married couple offers you plenty of opportunities to share wonderful memories. It’s a time for celebration and looking forward to many years to come.

Commemorating this important time in your life can be easy to forget or shrug off in the excitement of your engagement. Many soon-to-be fiancés make the mistake of focusing so intently on planning the perfect proposal that they forget to document it (or sneakily arrange for their girlfriends to get their nails done for ever-important ring photos). Couples assume they’ll take good photos at the wedding, and thus don’t need decent engagement photos. 

But proposals and engagements offer couples an excellent chance to document their relationships even before the big day.

Photo of a proposal taken by Jenna Lee
Jenna Lee is a photographer whose specialty is romantic photo sessions in Hawaii

Professional engagement photos can help to drum up excitement prior to the wedding and give you ample material to look back on afterward. And when a proposal takes place in a beautiful destination — say, Hawaii — you have all the more reason to make sure your experience is properly photographed. 

After years as a destination wedding photographer in Hawaii, Jenna Lee has some incredibly helpful and informative tips for couples considering taking their proposal and engagement photos in Hawaii and elsewhere. 

Jenna enjoys adventure wedding photography — working with couples who want to take their wedding photos in unique, remote, and difficult-to-find destinations. She has a strong understanding of how to create the best professional photography experience in Hawaii, specifically, as well as how to truly serve the personalities, desires, and unique relationships of all the couples she works with. Jenna’s advice helps couples get gorgeous Hawaiian photos that truly match who they are and what they want.

Hire a Pro: It’s Absolutely Worth It

If you only take away one thing from Jenna’s advice, let it be this: Hire a professional photographer for your photos. This is especially important in Hawaii, where permits, laws, and local regulations are stricter than in many other areas. Planning a wedding is stressful (and costly enough); you don’t need the added burden of paying a fine for accidentally taking photos in the wrong place.

“A legit professional will not only provide guidance on which locations this can legally take place but will pull a permit for the shoot as well,” Jenna said. “This is incredibly important to ensure that no one ends up with a ticket, gets in trouble for trespassing, or unknowingly traipses through a significant or sensitive cultural space. A nice Instagram doesn’t always mean the photographer is a legitimate business. However you’ll know those who pull permits are.”

couple on rocks, turtle below
Couples who work with a professional photographer enjoy higher quality pictures.

Working with a professional photographer also comes with the benefit of, well, professional-quality photos. Your friends and family may be better-than-average at using their smartphone cameras, but that doesn’t compare to professional-grade photography equipment or a keen understanding of light and color composition or posing. 

Many couples who haven’t worked with a professional photographer and are unaware of the price of the service will immediately balk at the cost. But trust us: Having good photos is worth the price. You don’t want to end up kicking yourself years down the line for unflattering but cheap photos. When you love your proposal, engagement, and wedding photos, it’s worth every penny. 

Choose the Right Island for Your Personality

If couples decide to have a photo shoot in Hawaii, they should narrow their location down to the island, depending on what they want. Hawaii struggles with overcrowding on beaches, so many photographers keep individual locations secret, instead focusing generally on a given island. “Most of us just post the island rather than the location,” Jenna said. “Once couples book, we go over location options.” 

Jenna loves working on each island in Hawaii, but she finds that some traits stand out for each island. While she works on every island, it’s a good idea to have a sense of which island you want to be on before you talk about specific locations with a photographer.

Oahu is the busiest island, but it has tons of diversity of location. Jenna noted its gorgeous waters and majestic mountains.

Maui is home to a lot of resorts. It’s a bit drier, with the exception of Road to Hana, Iao Valley, and Kapahulu. Couples can enjoy wine tasting, goat farms, and beautiful sunsets on the island.

couple kissing in the rain
Each of Hawaii’s islands has a different terrain and culture that will appeal to different couples.

Jenna described Kaui as having more of an “Old Hawaii vibe.” The island has gorgeous green mountains and lush green terrain.

The Big Island is the largest island in the Hawaiian chain, and its massive size provides diversity in landscapes, including lava rock terrain. The island is more sprawling, requiring more driving to get around. But for some people, that’s totally worth it. “Those who love the Big Island LOVE the Big Island,” Jenna told us.

Lanai, called “the Billionaire’s Island,” is the most expensive place to stay. It’s the driest island and definitely on the quieter side.

“Google some photos of each, do a little reading, and determine which island is for you!” Jenna suggested. “Some photographers will travel between islands. We do!”

Couples should be aware of the difference between taking photos on public or private land. Jenna often recommends going legally on private land, as this often comes with more freedom, especially if you want to use signs or props in your photos. 

“Legally, you can’t set anything up like this on the beach (as harmless as it may seem); it’s been happening a ton the past few years with IG, so they have really been cracking down on this, and because we want to ensure your proposal is INCREDIBLE, best to avoid any potential conflict,” she said.

Plan for the Perfect Photo With Jenna Lee

Planning for a wedding necessitates logistical perfectionism, and that starts long before you say, “I do.” Your proposal and engagement photos are one area that you definitely want to get right. But in a setting like Hawaii, making sure that you do everything right on your own is more stress than you and your partner should take on. Working with a professional makes the whole experience more relaxed, and the photos you get will be better than you could dream of.

When we asked Jenna for her advice, she got right into the details of permitting, location, and even timing — Jenna suggested sunrise on weekdays. She understands the intricacies of taking fantastic photos, particularly in Hawaii, and how to get the images that are perfect for couples. That kind of service is immensely useful, especially for couples visiting Hawaii on vacation and trying to plan a wedding at the same time. 

couple on beach
Jenna has delivered gorgeous photos for countless couples all over Hawaii.

Jenna has photographed couples all over Hawaii and delivered truly gorgeous photos that they love. Most importantly, she works closely with her clients to deliver the perfect photos set in the location they want and doing whatever they want to do in their pictures. 

“I’d be lying if I said being an Adventure Wedding Photographer wasn’t one of my favorite things to do,” Jenna said on her website. “I know I’m biased, but my couples really are the best.”