Every year there’s one trip on my calendar that I don’t move for anything, and that’s the Rockwell Trading Mastermind on Grand Cayman. On Friday, October 2, I packed a bag, left the van build behind for a while, and headed south for about ten days of island time. Part business, part beach, and all the way worth it. I’ve been to Cayman several times now, and it never gets old.
If you’re new here, hi! I’m Jay. Camy and I run CJ Travels (you might also know us as CJ VanVentures), where we share our travels and the slow, sawdust-covered process of turning a Ford Transit into our home on wheels. This trip was a little different from our usual road stories, so let me walk you through it.
Why a Trading Conference Is on a Travel Blog
Here’s the short version of how this whole thing works. I’m a retired Army veteran, and these days I live off options income. I mostly trade the wheel strategy and earnings trades, and I’ve learned a lot of it through Rockwell Trading and their PowerX Optimizer software. (If you’re curious about the tool I use, I wrote about it here: PowerX Optimizer.)
That trading is what funds the travel side of our life, including this blog and the van. So when the Rockwell crew gets together for a Mastermind, it’s not a vacation I’m sneaking in. It’s a tune-up for the engine that makes all the other adventures possible.
Quick note: I’m sharing my own experience, not giving financial advice. Trading options carries real risk, so do your homework.
Home Base: Seven Mile Beach
I stayed near the Westin on Seven Mile Beach, and I can’t think of a better place to land. The water is that ridiculous shade of blue you assume is photoshopped until you’re standing in it. Mornings were calm, evenings were made for walking the sand, and it was easy to get anywhere I needed to go.
My advice on where to stay? Anything on Seven Mile Beach is good. And the sunsets there are always amazing.
The Mastermind: Strategy by Morning, Beach by Evening
The working part of the trip ran Monday, October 5, through Thursday, October 8. The rhythm was just about perfect. Mornings were for trading and strategy sessions with fellow Rockwell Trading members, and evenings were for the beach.
I love this format. You spend the morning with sharp people who trade for a living, comparing notes, picking apart setups and talking through what’s working and what isn’t. Then, just when your brain is full, you trade the conference room for salt water and a sunset. Some of the best conversations of the week happened with toes in the sand rather than around a table.
If I had to boil this year’s sessions down to one line, it’s this: AI is here, so you’d better start using it.
So what am I changing in my wheel and earnings trades? First, I’m following my rules more closely. I’m also using AI to format my rules and make them more formal, and AI agents are now helping me pick trades.
My biggest takeaway, though, is that I’m building out my brain file now. We’ve been talking about it for a few years, and now I’m on board. That one probably deserves its own article, so stay tuned.
What I value most is the people. Trading can be a pretty solitary thing, just you and a screen. Getting together once a year with folks who speak the same language keeps me honest, keeps me learning and reminds me why I enjoy this.
Glowing in the Dark: Night Kayaking From Rum Point
If you know me, you know I’m always chasing unique experiences, and Friday, October 9, delivered one. With the conference wrapped, we headed to Rum Point for the Cayman Kayaks bioluminescence night tour.
It had been raining earlier in the day, and I’ll admit I wondered if we’d get rained out. Good news: light rain doesn’t spoil the glow. Once we were out on the water in the dark, every paddle stroke lit up. It’s one of those things that’s hard to describe and even harder to photograph. You just have to be there.
Friends had also suggested a Pampered Ponies horseback excursion as a backup plan in case the weather didn’t cooperate. We didn’t need it this time, but horseback riding in the water is at the top of my list for the next trip.
Of everything we do on Grand Cayman, the bioluminescent kayak tour is my favorite. Hands down.
My favorite part is just being on the water at night and listening to the guide. They point out the constellations, and you can see all the houses lit up around the bay.
More Island Favorites: Stingrays, Starfish and Caves
Kayaking isn’t the only thing on my must-do list. Here are a few more we come back to.
Stingray City. We always do the stingrays. Every time. It’s just so cool.
Starfish Point. Over by Rum Point, you can see starfish in the wild, right there in the shallow water, and even hold one.
The caves. We didn’t make it to the caves this trip, but I’ve done them on earlier visits, and if you haven’t been, you have to do the caves. They’re very cool, with bats, especially if you haven’t been in caves before. I’ve been in some big caves around the world, so they weren’t life-changing for me, but they were still very cool.
Exploring George Town: Shopping and Good Eats
I also spent time wandering downtown George Town for some shopping and dining. Anyone who’s followed us for a while knows food is a big part of how I travel. I’m happy at a five-star table or a hole-in-the-wall spot where the locals eat, as long as the food is good. Bonus points if there’s a nice Malbec on the wine list, or a solid stout or a local brewery nearby.
We’ve been to a ton of restaurants on the island over the years, but two stood out this trip.
Casa 34 was my favorite. It’s very lively and sooo friendly. We got a jug of margaritas, lobster tacos and some excellent guacamole, and the menu has all kinds of tacos and other dishes to work through.
Ms Piper’s came in a close second. It’s more of a dinner spot: quiet, romantic, with live music. I had the snapper, butterflied and grilled, about a two-pound fish. Honestly, the best fish I have had.
For something fancier, our friend Danny recommended Kojima Izakaya, a Japanese spot right on the water on the edge of George Town. The food was amazing, and the surprise was a beef rib someone at our table ordered. It was so tender it fell off the bone, and you could eat it with chopsticks. That’s not something I expected at a sushi place.
As for drinks, I always start with a Mudslide. That’s been my tradition.
What’s Next: Mastermind 2027
The Mastermind travels, which works out great for a guy who likes seeing new places. For 2027, the stops are tentatively planned for Cancun in February, Ireland in the summer and back to Cayman in September. Nothing’s set in stone yet, but I’ll keep you posted. Ireland and its stouts are already calling my name.
Wrapping Up
This trip is a big reason the rest of our travels happen. I come home with sharper trading habits, a few new friends and a couple of stories I’ll be telling for a while. Now it’s back to the Transit build, so Camy and I can start taking these adventures on the road together.
Have you been to Grand Cayman, or tried a bioluminescent kayak tour somewhere else? Drop a comment and tell me about it. I’m always collecting ideas for the next adventure.
Thanks for reading, and for following along with Camy and me. See you on the road!
