About
Twenty-five years here. Ten of them on a boat.
I am Cyrus Perry. I started photographing my friends around Maui, took my first paid session because someone messaged me on Instagram, and have not really stopped since.
How it started
One message, in 2014.
I had been shooting photo and video with my friends around the island for a couple of years — portraits of each other, mostly, and a lot of landscapes. I was self-conscious about the work. Then somebody found it on Instagram and asked whether I would photograph them.
She loved the photographs. I got paid well. And the thought that followed was the one that starts most of these businesses: this was fun, it was not hard, and people will pay for it.
For the next eight years it stayed a side thing while I worked three or four days a week on a boat. I crewed for Trilogy for a decade — part of that job was teaching people to snorkel, which is a higher-stakes version of getting a nervous person to trust you than photography will ever be.
2022
The boat stopped making sense.
My first daughter was born. I get motion sickness without enough sleep, and a new baby is not compatible with being useful on a boat at six in the morning. So I went full-time on photography and video, and have shot around two hundred sessions since.
The trade was a better schedule, more time with my family, and not coming home completely wrung out by ten hours in the sun. The cost was everything that comes with running a business. I would take the same deal again.
What I actually want
To be one of the good parts of your trip.
Most activities on Maui get two hours or more of your time. I usually get forty-five minutes, and I would like them to count.
- 01
It should not feel like a photo shoot
Stiff and robotic is the failure state. The goal is that afterwards you say it was fun, and then you say the photos are good.
- 02
The work should speak first
Warm, vibrant colour that looks like the island you actually visited — not muted and moody until it could be anywhere.
- 03
And the reviews should back it up
254 of them at a 5.0 average, from people who had no obligation to write anything.
The local knowledge
I know what the wind is doing at two in the afternoon.
Twenty-five years living here and ten working on the water means I can tell you what an average day will do — where the trades will pick up, which beach will be blown out by the afternoon, which side of the island stays dry when the other one is getting rained on.
I am also an admin of one of the Hawaii photographer Facebook groups, which is close to ten thousand people. That is where I send anyone I cannot fit in — because a visitor who cannot book me should still end up with good photographs.
Community
Free sessions for families who lost their homes.
If you lost your house in the Lahaina or Upcountry wildfires, you most likely lost every photograph in it. I photograph those families for free — no package, no charge, and I will turn down the tip if you offer one.
Frequently asked
The questions I get most
I pick the location. I ask where you are staying, then choose from a short list of permitted beaches on that side of the island — the ones away from the hotels, with room to move and better backdrops. I will send you photos of the options and tell you why I am recommending each one.
If your family already has a colour you always wear, wear it — this is your session, not mine. If you want a recommendation: white and light earth tones photograph beautifully here, and they are what most people end up choosing.
I am going to tell you sunrise, and I mean it. The beach is empty, the trade winds have not picked up yet so nobody is fighting their hair or their dress, and the light 30 to 45 minutes after sunrise is soft enough that everyone can keep their eyes open. Sunset is beautiful when the colour pops — but that is closer to a one-in-three night, and you are working against the wind.
Your gallery lands 2–3 weeks after the session. Every photo in it is fully edited — you are never picking from raw files and hoping. I text you and email you when it is ready, because some people never check one or the other.
Your package number is the number you choose — but I edit two to three times that many, so a 45-minute session means 100 to 200 finished images to pick 50 from. Extra images are $35 each, or $200 unlocks the whole gallery. Leave me a couple of honest reviews and I unlock it for free. About nine in ten people take that option.
Next step
Tell me where you are staying.
I will come back with a beach, a time and the reason for both — usually inside the hour.