Sean already knew the answer. He just hadn’t asked the question yet.
He and Irene were already married — a civil ceremony in the Bay Area, practical and intentional, the kind of thing you do when school and timing and life don’t bend to romance. The wedding was real. The commitment was real. What was missing was the moment she deserved: the ring she had always wanted, the question asked the right way, the memory she would keep.
The Catalina trip was the plan. A honeymoon-style getaway, framed as an anniversary celebration. She thought they were going on a backcountry tour, and little did she know, Sean had planned all along, making sure the crew was in on this whole surprise.
The Ring
Months before the trip, Sean had gone to the mall with his cousin. He told Irene they were browsing. He slipped away to a Bulgari store, put down a deposit, and spent the next several weeks texting a Bvlgari representative about a ring being shipped from Europe. Since the ring had to be custom made into her size, it had to be made, shipped, tracked, and collected just days before they leave for their honeymoon trip to Southern California.
He picked it up without her knowing. He hid and packed it carefully, and carried it to the island as if it is just another carry-on item.
The Backcountry Tour
The tour began at 5pm, pick-up spot at previously discussed parking lot in Avalon, with driver Orlando in a black Jeep Wrangler. Orlando, originally from Panama, has lived on Catalina Island for 29 years, who knows every road, every animal, every story the island holds. He is a natural storyteller, no convincing needed.
The team of 3 had coordinated before this day. The cover story was set – Orlando would play his role as a tour guide, Stephanie as the photographer that’s part of the tour.
What followed was one of the most memorable drives I have been on.
Orlando took us up Stagecoach Road — the same single dirt road that once connected Avalon to the island’s interior by six-horse carriage, a trip that took two hours going up and eighteen minutes coming down, which tells you something about the horses and something about the cowboys. He talked about William Wrigley, who bought the island in 1918 and planted 500 eucalyptus trees along the road at his wife’s insistence after she nearly died of fright on her first descent. He explained island dwarfism and island gigantism — the phenomenon that makes the Catalina fox smaller than any mainland fox, and the bison subtly different from those in Yellowstone, and everything on the island fascinatingly shaped by its isolation.
He talked about the bison. All fourteen originally brought to the island in 1924 by novelist Zane Gray, who needed them for a Western film and then — somewhat irresponsibly — simply left them when filming wrapped. Fourteen became four hundred.
On our tour, we saw nearly a dozen of them that afternoon, including one enormous male ten feet from the Jeep who seemed entirely unbothered by the cars and laughters.
Planning your own proposal on Catalina? We’ve put everything we’ve learned from photographing on the island into one place: Guide to Catalina Island proposal and wedding locations.
The Proposal
At this scenic harbor overlook, Orlando stopped the Jeep and told them to sit at the bench while we left and went to set up a little picnic 50 yards away. Nothing over the top. Just something nice, sweet, and minimal, exactly what Irene appreciates.
When they came back down and saw what had been prepared, Irene paused.
Sean turned toward her.
“The past couple of years that we’ve been together, you have made me realize what it feels like to be a kid again. You have given me the safe space and the opportunity to feel love, to feel seen, to feel supported, understood and vulnerable. And I thank God every day for blessing me with your presence. For all the memories, adventures, laughter, moments that we share. And I can’t wait to do it with you for the rest of my life.”
He paused.
“I know we’re already married. But I wanted to give you the proposal of your dreams.”
He went down on one knee.
“Oh my God,” she said. “I’m gonna marry you for 100 times. Yes.”
After the yes, she found out the ring was shipped from Europe. She found out about the deposit, the sizing missions disguised as casual browsing, the weeks of coordination.
“You’re full of surprises,” she said.
She is right, he had been planning this since before they got married at City Hall.
A Different Kind of Proposal Story
Most proposals I photograph are a first — the first big question, the first yes. This one was something else – Sean and Irene had already chosen each other in the most practical, legally binding way. This proposal was not about the question, it was about the moment she deserved — the one that got skipped not from lack of intention, but from the life constraints.
Orlando said something on the drive back to Avalon that I wrote down: “Now you have a different story. This is a lifetime memory for both of you.”
We got back to town right when sun had gone down the horizon.
Planning a Proposal on Catalina Island?
The Catalina backcountry is only accessible through permitted vehicles and guided tours — the interior is protected Conservancy land, and you cannot simply drive in.
For couples considering a proposal in the backcountry:
Coordinate with the tour company in advance. The driver can be looped in on the proposal plan, which makes timing and positioning significantly smoother. The tour guide was essential to making the setup work without raising suspicion.
There is no cell service in the backcountry. All coordination needs to happen before you leave Avalon, or through the driver directly. Confirm logistics before the pickup.
Flowers must come from the mainland. There are no florists on Catalina Island. If you want fresh flowers at the proposal, plan for them to travel with your photographer or be sourced on the mainland ahead of time.
The tour itself is part of the experience. A backcountry proposal doesn’t feel like a location backdrop — it feels like an adventure that happens to culminate in a moment. Orlando’s narration and the island’s wildlife made the entire afternoon feel alive in a way a static venue cannot replicate.
100% Private. The backcountry is not accessible to casual foot traffic. A scenic harbor overlook has none of the public crowd like the popular spots in Avalon.
Catalina is one of the few places near LA where a proposal can be genuinely private, but the logistics take planning — here’s a blog about what to know before booking a Catalina proposal, including ferry timing and setup limits.
Ready to Plan Your Own Surprise Proposal?
Whether you’re local or traveling in — we’d love to help you plan a seamless experience
and document every honest, beautiful moment. 💍✨
