Two Decades of Cruising

The Robertsons look back on the last twenty years at sea, and what the future holds.

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Playing in Columbia in the early days of cruising Del Viento.Michael Robertson

It was twenty years ago today. St. Pepper may have been busy somewhere teaching musicians, but Windy and I were nowhere near that scene. Earlier that December we’d cast off the dock lines in Ventura, California, and turned left. It was just the two of us—both in our 20s—aboard my little Newport 27, that was also named Del Viento. We barely knew each other, but before our 8-month voyage from Southern California to Southern Florida was over, I knew I wanted to marry her.

Last week, as we prepared for bed in this little house in Ajo—the one we’re camping in because, as of now, it has no appliances, no heat, no hot water, few doors, non-functional windows that are spray-painted over, and a broken cement swan fountain in the front yard—I thought to ask Windy what she’d have done on that crisp Friday morning 20 years ago if she could have seen the future.

“Not how the future played out from then to now, just a snapshot of this moment. You'd get to see the mattress on the floor we sleep on, this truck we’re driving that was already 8 years old way back then, and the gaping holes in the ceilings and walls.”

“I’d have run like hell.”

“Yeah, me too.”

More Photos:

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Me carrying the dinghy along a Cuban beach. Our old Avon Redcrest rowed so poorly that it was easier to carry it along the shore to the closest point of approach.Michael Robertson
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With our dear friend Tim, still in the Canal. There were five of us living aboard little Del Viento for our 2-day transit.Michael Robertson
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Windy pointing out a howler monkey to my dad somewhere in the Panama Canal.Michael Robertson
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Sailing into Acapulco.Michael Robertson
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Windy rowing away from some curious sperm whales in the middle of Mexico's Sea of Cortez.Michael Robertson

In our twenties, we traded our boat for a house and our freedom for careers. In our thirties, we lived the American dream. In our forties, we woke and traded our house for a boat and our careers for freedom. And here we are. Follow along with the Roberston's onboard Del Viento on their blog at