I’m a few hours out. In the morning I’m headed to Key West to meet a group of startup founders, adventurers and even an Olympic Gold medalist.

On Saturday we’re planning to sail for Havana where we’re slated to meet members of the island’s burgeoning tech and startup scene. And I have no idea what to expect when I get there…

The island’s oppressive Communist regime is anything but forward in their thinking. Freedom of speech, technology, the Internet, all of it’s highly policed. But strangely enough, it’s very possible (I hope) that even under these conditions, innovation is incubating. Crisis precipitates change, and this is a nation forced to fend for themselves, forced to create.

I wonder: can an entrepreneur class exist in a country where most of its GDP comes from U.S. remittances? Is this nation truly in a time warp, or are locals more advanced than we think? Is there an infrastructure in place to support technology?

Right now, to me, it’s all a question mark. But it’s an exciting one, because I’m going to be part of a group training, advising, and working with local entrepreneurs at meetups in Havana, at the Bay of Pigs, and at former coffee plantations throughout the country. All spectacular historical locals, all in a state of flux as the island is just now opening up to the U.S. after years of a crushing embargo.

If that’s not enough, the group I’m traveling with — led by the founders of Cotopaxi, an outdoor gear startup that donates to charities based on purchases — is planning to kayak from Havana to Key West, 103 miles, over a period of 24 hours. Each mile is being donated to to Cuban startups. And I’m going to be part of that, too.

I know, it’s crazy to kayak in open-water, especially during hurricane season, and only a week after one hit the area. And what real training do I have?

But — I’m going to be doing it in a relay format, which means I’m likely not paddling the whole thing. And there’s a great team to support us. That group includes the Olympian Joe Jacobi (gold winner in paddling in ‘92), and a support boat escort (the same one that chaperoned Diana Nyad’s historic swim in 2013). I’m not trying to prove anything, and I know how dangerous — and crazy — this sounds. So if I’m not feeling comfortable at any time, back to the support boat I will go.

The idea of being in the water, in the dark, is extremely scary. So is high tide, and sharks, which team leader Davis Smith told me “we will see.” However, Davis described them to me as the small guys: reef sharks and blue tips, maybe a hammerhead. But that doesn’t really make me feel any better. They’re all terrifying up close, no matter what their size.

A lot of people advised against going. At least for the kayak part. It sounds dangerous, it sounds nuts. And I agreed. But I think the relay format will mitigate those concerns, and I’m going into it looking to participate, not show off.

No matter what, this is going to be an adventure, a chance to see Cuba as it is now, before the influx of dollars reverts the island back to the Carribbean Las Vegas of the ‘40s and ‘50s. A Club Med will be here in five to 10 years. Spring Breakers will come too, it’s only a matter of time.

I want to see the country before all that.

I want to see what the Cuban startup ecosystem is right now, especially given Cuba’s extremely limited resources, minimal Internet access, and extreme poverty. The question remains as to what I’ll find. If you’re interested, follow along on Twitter and Instagram, and look forward to my piece coming in TechCrunch when I get back. The kayak portion of the trip should be around September 9 or 10, weather permitting. Wish me luck.