BASED ON OAHU + SERVING HAWAII + CHICAGOLAND AREA
jenna lee pictures
Where love meets adventure.
808.339.6659
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Oahu Proposal Photographer
Gorgeous, Fun, Stress-Free Proposal Photos in Paradise
Oahu Proposal Photography & Videography
Wild-hearted love. Epic island backdrops. Emotional photo + video storytelling for your once-in-a-lifetime YES.
So—you’re ready to pop the question in paradise?! 😍 First off, I’m already excited for you. A proposal in Oahu is one of the most magical experiences you can give your person, and capturing it the right way means you’ll relive those happy tears, the jaw-drop moment, and that YES forever.
Here’s the thing: you only get one shot at this. And trust me, it deserves to be documented in a way that feels alive—not stiff, not cookie-cutter, but full of the energy, nerves, and joy that make this day uniquely yours. That’s exactly what we do. My team and I are not just Oahu proposal photographers—we’re expert storytellers, adventure-lovers, and sneaky paparazzi (in the best way). We know how to blend into the background until the exact second you drop to one knee—and then capture it all in photos and film so cinematic it’ll feel like your own highlight reel.
🌴 Beach sunrise with nobody around? We got you.
⛰️ Cliffside overlooking the ocean? Been there, know the trails, know the light.
🌺 Secret garden proposal? Say no more—we’ll make it magic.
With 15+ years of photographing surprise proposals, engagements, and weddings on Oahu, we know the best spots, the best light, and the timing tricks to keep it stress-free. From helping plan the logistics to capturing every laugh, kiss, and teary-eyed “yes,” we’re there to make sure nothing gets missed.
Why couples trust us with their proposals:
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We know Oahu inside and out. Beaches, mountains, hikes, waterfalls—you name it, we know how to shoot it.
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Photo + video packages. So you don’t just remember it—you see it, feel it, live it again and again.
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Adventure is our thing. We’ve pioneered epic proposal + adventure photography in Hawaii for well over a decade.
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We make it fun. No stiff posing, no awkward vibes—just real emotions and killer backdrops.
If you’re dreaming up the perfect Oahu proposal, let’s make it unforgettable. You focus on the love, we’ll handle the magic.
✨We’ve captured proposals for couples of all walks of life and all around the world — from destination travelers and local families to LGBT couples and beyond — and we’d love to capture your unique love story!
A Signature Jenna Lee Pictures Experience at a More Accessible Level
theTRIBEphoto is the heart of our mid-tier offerings within Jenna Lee Pictures — a handpicked team of photographers and filmmakers who bring the same fearless creativity, cinematic style, and love-driven approach that built our reputation worldwide.
We designed theTRIBEphoto to make our signature visual storytelling more accessible, giving families and couples the chance to experience that adventurous, wild-hearted JLP energy at a friendlier investment.
Every TRIBE artist works closely under Jenna’s creative direction and mentorship, ensuring the same dedication to connection, artistry, and unforgettable storytelling that defines our top-tier Jenna Lee Crew.
Two tiers, one vision: capturing your love story with passion, artistry, and soul.
All starting pricing is through our TRIBE squad.
Choose Your
PROPOSAL PHOTO Experience
Two Ways to Capture Your “Yes” 💍✨
We offer two incredible photography + videography teams under Jenna Lee Pictures, so you can choose the vibe and investment that feels right for your proposal:
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theTRIBEphoto
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Every shoot is led by one of our TRIBE photographers — bold, talented, and rooted in our signature wild-hearted style. They bring the energy, connection, and storytelling Jenna Lee Pictures is known for, at an accessible price point.
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JENNA LEE PICTURES
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Our world-class photographers, including Jenna herself, deliver boutique-level coverage with premium artistry and personalized attention. Every detail, every emotion, every fleeting moment is captured with intention — creating imagery that feels elevated, soulful, and unforgettable.
Select your session type below to see pricing for both tiers.
PROPOSAL COVERAGE
1 HOUR
One of our talented TRIBE photographers will stealthily capture your proposal moment and all the emotions that follow. With a full hour together, there’s time for genuine candids and beautiful portraits afterward — giving you a complete collection of memories from your “YES!” in paradise.
Starts at $550
1 Hour photo / video
Stealth mode: activated. Your TRIBE photographer + videographer team will capture the moment you pop the question from every angle — in both stunning photos and emotional video. With a full hour, we’ll document the “YES!”, the reactions, and a mix of portraits afterward. You’ll receive a full photo gallery plus a cinematic highlight film so you can relive (and share!) the magic forever.
$1,495
PROPOSAL COVERAGE
1 HOUR
Our world-class Crew delivers boutique-level artistry and intentional coverage for your proposal. From the anticipation leading up to the big moment to elevated portraits after, every detail is captured with premium storytelling. Perfect for couples who want their once-in-a-lifetime “YES!” documented in a way that feels timeless and unforgettable.
Starts at $750
2 HOURS • PHOTO •Multiple locations
Experience boutique-level storytelling with one of our world-class Crew photographers. With two full hours, you’ll enjoy coverage of your proposal, portraits across multiple breathtaking locations, and premium drone footage to elevate your gallery. Every detail, every emotion, every sweeping backdrop is captured with intention — creating a collection as unforgettable as your proposal itself.
DRONE INCLUDED • 2 HOURS
$1,495
Make it Unforgettable
Favorite
PROPOSAL Spots
on Oahu
Waikiki Beach - ICONIC VIEWS • WALKABLE ACCESS • BEAUTIFUL BEACH • DIAMOND HEAD • LOTS OF VARIETY • EPIC SUNSETS (BUT BUSY!) • NO DRONE
Lanikai Beach - WHITE SANDS • AQUA WATERS • ISLAND-VIEWS •BEAUTIFUL SUNRISE •ISLAND- VIEWS •EPIC DRONE SPOT •NO RESTROOMS
Kualoa Regional Beach Park - TOWERING GREEN MOUNTAINS •PEACEFUL BEACH •ISLAND VIEWS •AMPLE PARKING •RESTROOMS •NO DRONE
KoOlina Beach - CALM WATERS • RESORT VIBES • GORGEOUS SUNSETS •ONLY RECOMMENDED IF YOU'RE STAYING OUT IN THAT AREA.
Hoomaluhia Botanical Gardens - EPIC MOUNTAINS • JUNGLE VIBES •AMPLE PARKING •RESTROOMS •EPIC SPOTS •SPECIAL •NO DRONE
Kawela Bay - CALM WATERS • FOREST ON THE BEACH •JUNGLE VIBES • TURTLE HAVEN • TURTLE BAY ADJACENT • NO RESTROOMS • CAN DRONE
Sunset Beach - BIG BEACH • EPIC SUNSETS • CONVENIENT NORTH SHORE LOCATION • PARKING CAN BE TRICKY • CAN BE BUSY • CAN DRONE
Sandy's Beach - BIG BEACH • EPIC WAVES • LOTS OF PARKING • GORGEOUS SUNRISE • LAVA ROCK • RESTROOMS NEARBY • CAN DRONE
*Once you become our client, you get access to our FULL Locations' Guide!
Real Couples,
Real Moments.
Every image is a piece of your story — captured with heart, edited with intention.
What to Wear
For your proposal
on Oahu
🌅 What to Wear for Your Hawaii Proposal
Keep it light, breathable, and beachy — you want to feel good in what you’re wearing, because it always translates in your photos. The golden rule? Keep it timeless. Years from now, you’ll want to look back and think “Wow, we look amazing!” — not “What were we wearing?” 🥴
Timeless Tips:
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Stick with soft neutrals, earth tones, or flowy classics (linen, cotton, light layers).
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Avoid bold logos or super-trendy patterns that might date the photos.
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If one person wears a pattern, keep the other solid so the outfits complement.
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No neon. Trust me.
Colors that pop in Hawaii: I personally love a little boldness! A red dress floating in the ocean, or florals inspired by the plumeria + hibiscus around Oahu look incredible against the ocean, cliffs, jungle, or Ko‘olau Mountains.
🌸 Getting Your Partner to Dress Up Without Spoiling the Surprise
This is the tricky (but fun!) part:
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Sunrise is super easy in Hawaii thanks to the time difference. You’ll be up early anyway, so convincing them to get ready isn’t as tough as you’d think.
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Tell them you’re going to a really nice breakfast reservation (which also makes sense for sunrise timing).
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If you want them in something timeless, suggest “cute island outfits” — think sundresses, button-ups, linen, etc.
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Keep it casual but elevated: like they’re dressing up for vacation, not a wedding.
🌴 Other Outfit Tips
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Bring a change of clothes! Many couples switch into something more casual (just be ready to change “Hawaii style” — under a towel).
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Think of your wall art. If you want to hang your photos at home, wear colors that complement your space.
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Above all else — let’s capture you. Your style, your love, your story.
Santiago D.
"I hired Jenna for a surprise engagement shoot on Maui and her and Sean were absolutely amazing! Jenna was very helpful recommending locations and the best time to do it based off of the lighting, the side of the island we were on, etc. My fiancé and I walked out on the beach and she had no idea what was going down. Jenna and Sean were camouflaged as a regular beach people until I made my move then they sprung up without missing a beat. Afterwards they drove us to another perfect location and we got hundreds of amazing pictures. They did so much more for us than I could’ve imagined. They are both so awesome and talented and I’m very grateful that we had them there on our special day."
Cory A.
"Choosing Jenna to capture our proposal and engagement photos was one of the best decisions we could have made. From start to finish, she delivered not only stunning, high-quality images but also an unforgettable experience. Her expertise, attention to detail, and thoughtful guidance turned our vision into a beautiful reality. Thanks to Jenna’s creativity and foresight, the entire shoot was seamless and genuinely magical, an experience we’ll treasure forever. We wouldn’t hesitate to work with her again for any future photography needs, and we’ll be recommending her to everyone we know. A heartfelt thank you to Jenna and the entire JLP team for making our special moment truly picture perfect."
Jessica F.
“Have customers review you and share what they had to say. Click to edit and add their testimonial.”
"I booked engagement photos through Jenna Lee while in Hawaii and it was the best decision we made! Cody was our photographer and he absolutely killed it. he made us feel so comfortable and the process so enjoyable. and our photos are incredible. Setting up the pictures with her team was seamless and they were very easy to communicate with. 1000% recommend!"
💍 Oahu Proposal FAQ
Q: How does proposal photography work on Oahu?
We usually recommend one of two approaches, depending on your style and comfort level:
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The Ninja Approach 🥷
We stay hidden or blend in with beachgoers, waiting for the big moment. As soon as you drop to one knee, we stealthily capture the surprise, the reactions, and all the emotions that follow. This is perfect if you want your partner to have no idea it’s coming. -
The “Photoshoot” Approach 📸
We set up a regular couples session — your partner thinks it’s just a fun photoshoot on the beach. Then, partway through, you pop the question! This option makes it easy to ensure both of you are dressed and camera-ready, and it flows seamlessly into stunning portraits afterward.
Both approaches work beautifully, and we’ll help you choose the one that fits your vision and personality best.
Q: What’s the best time of day to propose in Oahu?
🌅 Sunrise is our favorite! The beaches are quiet, the light is dreamy, and thanks to the mainland time difference, 6am in Hawaii feels like 11am to your body clock — so it’s surprisingly easy to wake up for. Plus, you’ll beat the traffic and the crowds, and have plenty of time to capture gorgeous shots afterward.
🌇 Sunset can be beautiful too, but the beaches are usually packed, traffic can be stressful, and once the sun drops, we lose light quickly (unless you want a true night session). That’s why sunrise almost always wins for proposals!
Q: How do I get my partner to dress nicely without giving away the surprise?
This is the #1 challenge — but don’t worry, we’ve got hacks! 😉
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For sunrise, say you’ve planned a special breakfast reservation at a resort — perfect excuse for a sundress or button-up.
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For sunset, frame it as a date night dinner so dressing up feels natural.
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Keep the vibe: “vacation nice” — not overly formal, just elevated and timeless.
That way, they look amazing and never suspect the big moment is coming.
Q: What should we wear for our Hawaii proposal photos?
Keep it light, breathable, and timeless:
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Neutrals, earth tones, or island classics (linen, cotton, flowy dresses).
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Avoid logos, neon, and clashing patterns.
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If one of you wears a print, keep the other in solids to complement.
🌸 Want to stand out? A bold pop of color (like a red dress or tropical floral) photographs beautifully against the ocean, cliffs, jungle, or Ko‘olau Mountains.
Q: What if it rains on the day of our proposal?
Don’t stress — Hawaii weather can look dramatic on the forecast, but most showers are quick and pass within minutes. 🌦️ Often, rain brings the most epic light and rainbows right after!
If the weather is truly uncooperative, we always have a backup plan:
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Shift the time or location (sunrise often helps dodge afternoon showers).
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Find a nearby sheltered spot for the proposal.
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Reschedule if absolutely necessary (rare, but we’ve got you covered).
Either way, your proposal will still be unforgettable — sometimes those moody skies make for the most magical photos. 🌈✨
Q: Can we bring a change of clothes for our Hawaii proposal shoot?
Absolutely! Many couples switch into something more casual or beachy after the “YES!” We don’t mind outfit changes at all — just keep in mind:
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You’ll likely change Hawaii style (under a towel or behind palm trees 🌴).
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Changes need to fit within your session time.
It’s a great way to get variety in your photos!
Q: What are the best locations for proposals in Oahu?
Some of our favorite Oahu proposal spots include:
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Waikiki Beach – classic Hawaii vibes with ocean + palm trees
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Eternity Beach – Epic beach cliffs and gorgeous beach cove.
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Kualoa Ranch – Jurassic Park cliffs and epic backdrops
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Crouching Lion / Kahana Bay – adventurous mountain scenery
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Lanikai Beach – sunrise magic with soft sand and turquoise waters
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Hoomaluhia – Impressive mountains and gorgeous scenery.
We’ll help you choose the perfect setting that matches your love story.
Q: What should we bring for our Oahu proposal?
Not much — keep it simple! Just a few key things:
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💍 The ring (hide it somewhere safe but easy to grab!)
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🌅 A light blanket — perfect for cuddling up on the beach if you want to enjoy the sunrise together before you pop the question
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🧥 Optional: a change of clothes if you want a second look (just keep in mind outfit changes need to fit within your session time)
That’s it! No need to overpack — the focus is on the moment and the magic.
Q: Can we add videography to our Oahu proposal?
Yes! 🎥 Videography is one of the best ways to relive your proposal. Our videographers work in stealth mode to capture the moment in real time, along with beautiful cinematic footage before and after. You’ll receive a highlight film you can share with family and friends — plus a high-quality download to keep forever.
Q: Should I get insurance for my engagement ring before proposing in Oahu?
We highly recommend it! ✨ Between sandy beaches, ocean views, hikes, and travel, it’s always better to have peace of mind. Many jewelers offer insurance or you can add it to your homeowner’s/renter’s policy. Having your ring insured means you can focus on the big “YES!” instead of worrying about “what ifs.”
Q: Can we make our Oahu proposal more epic with signage, candles, or décor?
YES, absolutely! We partner with Designed With Aloha, a talented local team who can custom-create literally anythingfor your proposal. From gorgeous “Marry Me” signs and floral arches to candles, picnic setups, and totally unique custom designs — they’ll help bring your vision to life. Together, we’ll make sure your proposal is not just beautiful, but unforgettable. ✨
Serving All of Oahu —
Wherever Your Gorgeous Proposal Takes You
We capture proposals across the island — from the golden sands of Waikiki to the dramatic cliffs of Kualoa Ranch, the sunrise magic of Lanikai, and the wild beauty of the North Shore. Whether you’re dreaming of a hidden adventure, a beachfront “YES!”, or an intimate cliffside moment, we’ll meet you in the most breathtaking spot to tell your story. Planning something personal? We’d love to help create a proposal that feels true to you — from a sunrise beach cuddle to a jungle overlook surprise. 💍✨
WAIKIKI
225 LILIUOKALANI AVE
HONOLULU, HI 96815
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808.339.6659
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About Jenna Lee Pictures
Jenna Lee Pictures is an award-winning photography and videography team based in Honolulu, Hawaii. For over 16 years, we’ve been capturing love stories across Oahu — from surprise proposals and intimate elopements to full wedding celebrations. While Oahu is our home, we also photograph proposals and weddings on Maui, Kauai, and the Big Island.
Known for our bold, emotional, and story-driven style, we specialize in Oahu proposal photography, Hawaii engagement photography, and cinematic videography that preserves real moments and genuine connection. Whether it’s a sunrise beach proposal in Waikiki, a cliffside “YES” at Kualoa Ranch, or a family-filled celebration on the North Shore, Jenna Lee Pictures is here to capture your love story in a way that feels unforgettable.