For ten years, Scott DiBiaso has been the captain of Juno, a sixty-five-foot schooner owned by Robert and Melissa Soros and built by Gannon & Benjamin Marine Railway in Vineyard Haven. Scott lives in West Tisbury with his wife, Lila, and their children, eight-year-old Owen and five-year-old Ethan, when they aren’t with the boat in St. Barth’s during the off-season.

How did you become a career sailor?

I really just stumbled upon it. It was more luck than judgment. I didn’t realize you could make a career of it. I started doing deliveries each fall and spring to and from the Caribbean. At the end of a trip you’d get a check for $2,000, and I thought, “This is alright!” I would spend the winter skiing in Crested Butte, and I’d be flat broke at the end of the season. I just kept postponing looking for an actual job, and the next thing you know you wake up at forty and you’re still messing around on boats.

How does your schedule vary from summer to winter?

In summer, you’re on call. The owners are great. Juno is very special to them. They have children and it provides a platform for the family to enjoy the experience together. The end of July and all of August is very busy. We’re always in a ready-to-go situation, ready to receive guests. After mid-September we’re in maintenance mode for five or six weeks. Then everything gets taped up and stowed for the passage down to St. Barth’s.

By mid-December we’re back in ready-to-go mode, but the maintenance is never really complete. Every day you see something that needs doing. You say, “Didn’t we just do that?” but it was two-and-a-half months ago.

What’s the passage down to the Caribbean like?

It’s my favorite part of the job – no phone calls, just get from A to B safely and comfortably. You get into the rhythm of the earth. You see sunrise and sunset every day. You see that moonrise is fifty minutes later every night. You get in tune with the natural elements.

I’ve done thirty-plus passages and no two have ever been alike. You get huge, twenty-foot waves that are organized. Massive trenches and house-sized waves. You’re going up to the crests where you can see for ten or fifteen miles, and then slowly down, surrounded by walls of water where you can’t see a hundred feet. After a couple days you get used to the rhythm of the waves.

It’s absolutely the most beautiful thing, riding like a cork. It’s also the only time of the year I can read a book.