Sailing to Cuba with my son: an unforgettable adventure

I’m no sailor. I’m not even a boat person. But when a good friend invited me to sail to Cuba on a 42-foot Endeavour, I thought: hell yeah!

And what a ride!

Sailing to Cuba with my son: an unforgettable adventure

It’s been awhile since I had an adventure

And this time I had the honor and privilege to bring my 13-year-old son along for the ride.

First off, I have to say that prepping for the trip, going to Sports Authority and Walmart and some other shops to get prepped up for the journey was an adventure in itself.

I felt like Joe Banks in “Joe Versus The Volcano” before he takes off to the island of Waponi Woo.

We had to buy knives, snorkel gear, flashlights, shirts, food, and all kinds of other gizmos we didn’t have because we’re not people who camp or sail or do that kind of survival stuff everyone else might do.

When we were finally off, we met some serious cross currents and waves coming out of the Intracoastal waterway at Venice, Florida.

The boat was bobbing in all directions when then the anchor dropped. The only reason I didn’t freak was because I was holding on to dear life in the middle of that mess.

When we got out of that, we sailed nice and easy—as far as sailing goes— to the Dry Tortugas. From there we took of to Cuba on an overnight sail across the Gulf Stream in what I considered pretty rough seas.

We hit a couple of squalls, which is sailor speak for a damn storm.

I’m not going to lie. It was scary as hell. It was a full moon and the waves were big and the boat was crashing against them and bobbing and swaying like a buoy. I didn’t get seasick, but we were in the middle of nowhere.

Also read: Cuba´s vintage cars are cool, but not their exhaust

Sailing to Cuba with my son: an unforgettable adventure

But that’s sailing. And as I got used to it, I felt way better. It was, after all, an adventure.

Father and son sailing adventure

The best part of the trip was sharing it with with my son Finn. He´d just turned 13 and this was exactly what we needed.

We talked about all kinds of things, from school to the future, going through Cuba, sailing, making Youtube videos… We even talked about videogames.

Being in a boat for 10 days (we lived on the boat as we overnighted in the Dry Tortugas and lived aboard while in Havana), brings you closer. And sharing in the adventure makes you realize you need to do this more often.

Finn’s not usually a big talker and I will never forget lying in the V-berth with him at my side, our arms touching, as we talked about his experiences in sixth grade.

I was petrified, hoping nothing would happen to him on the trip. He asked questions about how digital cameras worked, and what Cuba was going to be like, whether they had WiFi, or phones.

One thing that hit me deep in my heart was his willingness to be a part of the adventure; to crew, and help and participate in all that made the sailing trip a success.

He was curious and willing to try anything. He did sleep a lot because of the Dramamine and the bobbing boat, but he was congenial, happy. And he never, ever, complained.

In the end, I think the trip made me realize he was not a little kid anymore. I came out of that short journey with a newfound respect for him. And I think both of us learned a lot about each other.

Although neither of us are quite ready to take off on another long sailing trip, the experience we had is something I wish for every parent and child.

The years go by fast. They grow up, we get old.

Sitting in a boat in the middle of the ocean wondering whether everything is going to be okay, whether you are going to come out of this adventure alive, makes you realize how important all the little moments in your life are.

What I learned from all this is that I want to share as many of those moments with him as possible, before he becomes a man.

Phillippe Diederich

Phillippe Diederich is a bilingual author and photographer born in the Dominican Republic and raised in Mexico City and Miami. His photography has appeared in The New York Times, Time magazine, U.S. News and World Report and other national publications. Phillippe's novels Sofrito and Playing for the Devil's Fire are both published by Cinco Puntos Press. He is the recipient of a PEN/Phyllis Naylor Working Writer Fellowship and the Editor-in-Chief of Viva Fifty!

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