Beyond the Finish Line with Roy Disney

Roy P. Disney and Pyewacket are no strangers to us.

We’ve long admired the seasoned competitive sailor and his racing yacht, following their wind-powered adventures across open seas over the years with admiration and excitement.

Having recently completed the 2025 Transpacific Yacht Race—a legendary biennial event that stretches from San Pedro, Los Angeles to Diamond Head, Hawaii—we caught up with Roy about what he deems the “best offshore race in existence.”

Hi Roy! Congrats on another successful Transpac race! Any highlights or standout moments from this year?

The race this year was atypical, and by that, I mean unusually long and slow. Our normal weather pattern stretched out and disappeared, making us sail well south, adding about 500 extra miles to the course.

But there are two memorable moments. First, the last 150 miles were windy and quite fast. Second, our finish—at sunset and off Diamond Head at speed, with our friends, families, and mai tais waiting. There is just not much that beats that kind of magic!

We love that you and your crew usually celebrate at the Tommy Bahama Waikiki Restaurant post-race. What are your absolute must-haves from the menu?

My all-time favorite TB meal is the Macadamia Nut Crusted Snapper paired with my favorite drink, the Mai Tai. It’s the ultimate tropical combo—tasty, very filling, yet still leaves you wanting more.

We’re so inspired by your connection to the deep blue. What’s one lesson from sailing that you’ve carried into everyday life?

Patience and management. The ocean is just bigger than you and more unpredictable. You can’t control what you can’t control! No matter how frustrated you become, it won’t change a thing.

So true! As we transition into the cooler months, what does Living the Island Life mean to you now?

It means relaxing, being in the moment, feeling the warmth of the sun, and savoring everything around you. What I love about Tommy Bahama clothes—and OluKai® shoes—is that they remind me of that great summer feeling and comfort, even in the fall.

Hot, cold, or in between, this state of mind is always where I would rather be.

Always. We’ve talked before about how you find magic in the everyday, but if you could sail anywhere tomorrow, what would your version of paradise be?

If I had the choice (odd phrase, really!), the first is Hawaii and the second is Tahiti. I guess I am an island boy after all!