I have been selling real estate in Puerto Rico for 32 years. For most of that time, when people on the mainland asked what I did, they pictured beaches and vacation homes. That's not the call I get anymore.

The people reaching out to me now aren't shopping for somewhere to spend two weeks in February. They're relocating their families, their teams, and their companies. Fund managers. Founders. Software people. And over the last few years, a growing share of them work in or around artificial intelligence.

I sell homes in Dorado Beach, which gives me a particular view of who's moving to the island and why. The tax incentives get most of the headlines, and yes, Act 60 is a real driver — I've written about it at length elsewhere. But the part that never makes the brochures is the community that's quietly formed here. The dinners where half the table is running a startup. Neighbors comparing notes on where to find good engineers. At some point Puerto Rico stopped being a place people escape to and became a place people build from. This October, that shift gets a moment of its own.

What's actually happening

On October 9 and 10, the Caribbean AI Summit comes to the Puerto Rico Convention Center in San Juan. It's the first large-scale AI conference the region has ever hosted, organized by PRAIC, the local AI community, which now counts more than 1,000 members. I'm on the committee helping bring it together, so I'll be upfront about having a stake in it. I'd be telling you to come either way.

Here's the shape of it. Up to 1,000 attendees. Five keynotes. More than 20 sessions across three tracks: one for business and strategy, one for the people actually building production systems, and one for anyone earlier in the journey who wants to get up to speed. There's a hackathon with $11,000 in prizes, built around solving real problems here in Puerto Rico and the Caribbean. Every session runs with live English and Spanish subtitles, which matters more than it sounds, because this island sits right where the U.S. and Latin America meet.

Why I think it's worth the trip:

I've watched enough rooms come together over three decades to know the valuable part is rarely the agenda. It's who you end up standing next to.

A first-year event has a quality the big conferences lose. You can actually get to the keynote speaker. You remember the people you meet. And because Puerto Rico pulls talent and capital from both the mainland and Latin America, the person next to you at the coffee break might be the exact partner, hire, or investor you've spent a year trying to reach from behind a screen. Connections made in a room of the right thousand people have a way of outlasting anything you write down.

If you run a company, this is a short flight to a concentrated pool of the people you're competing to hire. If you build things, it's two days to get genuinely current on where the field is heading. And if you've ever wondered whether you should be paying closer attention to Puerto Rico — as a place to visit, to expand, or to live — this is the easiest way I know to see it for yourself, with a real reason to be on the ground.

The practical part

For anyone coming from the States, this is simpler than most domestic trips. No passport. No international roaming on your phone. There are more than 400 flights a week from cities across the mainland, and San Juan in October sits at a comfortable 85 degrees. The Convention Center is the largest in the Caribbean, about ten minutes from the airport and minutes from Condado and Old San Juan, so the evenings take care of themselves. You'll even find the summit listed on Discover Puerto Rico, the island's official tourism site, which is a small sign of how seriously the island is taking this.

Early-bird tickets are $299, capped at the first 150 registrations. If you've been on the fence, my honest advice is to sort your flights and your room sooner than later. Good rooms in San Juan during a strong week go fast, and I'd rather you hear that from someone who lives here than learn it the hard way.

If you're thinking about coming and want the real-world details — where to stay, how to get the most out of two days here, or what a longer look at the island might actually involve, send me a message. I'm glad to point you in the right direction, summit or not. Putting Puerto Rico on the map for this kind of work is something I care about, and I'd like you to be part of it.

FAQS:

1. When and where is the Caribbean AI Summit?

The Caribbean AI Summit takes place October 9–10, 2026 at the Puerto Rico Convention Center in San Juan — the largest convention center in the Caribbean and roughly ten minutes from Luis Muñoz Marín International Airport, with Condado and Old San Juan just minutes away.

2. Who is organizing the Caribbean AI Summit?

The event is organized by PRAIC, Puerto Rico's artificial intelligence community, which now counts more than 1,000 members. It is the first large-scale AI conference the region has hosted. Christian Kleiner serves on the organizing committee.

3. What can attendees expect from the program?

The summit hosts up to 1,000 attendees across five keynotes and more than 20 sessions organized into three tracks: business and strategy, hands-on technical work for those building production systems, and a foundational track for people earlier in the AI journey. A hackathon with $11,000 in prizes focuses on solving real problems in Puerto Rico and the Caribbean. Every session is delivered with live English and Spanish subtitles.

4. Who should attend the Caribbean AI Summit?

The summit is designed for founders, operators, engineers, investors, and anyone evaluating Puerto Rico as a place to build, hire, or relocate. Because the island draws talent and capital from both the U.S. mainland and Latin America, the attendee mix is well-suited to founders sourcing hires, investors meeting operators, and builders looking to get current on the field.

5. How much are tickets and how do I register?

Early-bird tickets are $299, capped at the first 150 registrations. Given the limited early inventory and strong demand for San Juan hotel rooms during peak weeks, arranging registration and accommodations early is recommended.

6. Do attendees traveling from the U.S. mainland need a passport?

No. Puerto Rico is a U.S. territory, so travelers from the mainland do not need a passport, and mobile phones do not incur international roaming charges. More than 400 direct flights per week connect San Juan with cities across the mainland, and daytime temperatures in October average around 85°F.

7. Why has Puerto Rico become a hub for founders and technical operators?

The island has drawn a growing community of founders, fund managers, and software builders — including a rising share working in or around AI — pulling talent and capital from both the U.S. mainland and Latin America. The Caribbean AI Summit reflects that momentum and is the first regional event of its scale.