Set sail on your dreams!

Couple shares once-in-a-lifetime island adventure

Tyson Hayward has always dreamt of sailing. Raised in land-locked Calgary, Canada by a father who had competed in the Olympic trials as a Star-Class yacht racer, the call of a watery horizon always beckoned him. So, at his first chance, in his early twenties, he set off for the Virgin Islands. Working as a waiter, he earned his fins as a scuba dive master and spent a year exploring the underwater paradise of the islands. 

When his time was up, he returned to the States by catamaran from St. Thomas and eventually ended up moving to Paso Robles, where he started Spinnaker Financial. Content with his life here and successful in his mortgage brokering firm, he nevertheless still day-dreamed about the islands, a fact hinted at by his company’s name (inspired by the spinnaker sail used in yacht racing). 

Several years later, Tyson visited the islands again, chartering a boat for a niece’s wedding. “All we did all day was take people out on day charters, cook them hot dogs and entertain them,” recalls Tyson, “and I thought this would be a fun thing to do for a job.”

The seed was planted. Back home in SLO County, Tyson started dating his soon-to-be-wife, Katie, while also working on earning his 100-Ton Captain’s license. All the while, his hopes of returning to the Caribbean lifestyle grew into plans. 

Making their dream a reality 

Katie, who was already SCUBA certified, created a chartered boat business plan and developed a delicious guest menu of fish tacos, ahi nachos, bruschetta, crab cakes, a captain’s burrito and a variety of other tasty treats. In 2011, the Haywards embarked on their dream, moving to the Caribbean indefinitely to become Captain and First-Mate of a 50-foot catamaran. 

When they arrived, the skies were still as ultra-blue as Tyson recalled them being. The water was still as balmy and clear as his first dive, years before. The ocean extended out as far as the eye could see, and the islands they navigated were the absolute postcard picture of tropical living and luxury. 

“It’s some of the best sailing and SCUBA diving in the world,” Tyson describes, telling of the secluded coves and keys which can be reached only by boat.

But the lifestyle, it turns out, was not quite as idyllic as the view.

“That first trip was a little overwhelming,” Tyson reports with candor about the first tour they gave, for a B-list reality TV star from the show Wife Swap. “The guy was a plastic surgeon and his wife was a—“

“—Botox queen!” Katie chimes in with a laugh. “They were a little high-maintenance.” 

Steep learning curve

She explains that with that first trip they encountered a steep learning curve: Not only were they captaining their first boat, but they were also getting a crash course in hospitality and the challenges of being confined in a small space with often demanding guests. Cooking, cleaning, serving, repairing and chauffeuring piled atop the already taxing task of navigating relatively uncharted waters. 

Of course the work was not without its rewards. Tyson pulls out a picture of the two of them—with bronzed skin and blonde, sun-highlighted hair—smiling in front of an incredible island backdrop. 

“We got to spend Christmas in St. Barts, and New Year’s in Jost Van Dyke—which was one of the most memorable New Year’s Eves we’ve ever had. That was a lot of fun,” Tyson reminisces happily. 

“It was beautiful,” Katie adds, describing the yachts and cool dive sites they had the chance to explore, like the famous Wreck of the Rhône, a ship that sank in the 1800s. “We were surrounded by the 1 %. It was awesome.”

But after four months immersed in the Caribbean, the Haywards realized they had fulfilled their dream. Returning to the Central Coast, Tyson went back to the work he was really born for at Spinnaker Financial. Katie slapped on her signature Captain’s hat at her wine country tour company, Uncorked Wine Tours (she had worn the hat on a whim one day back when Tyson was earning his Captain’s license and has been known as “Captain Katie” ever since). 

Looking back and moving forward

Looking back, Tyson says, “The experience made us realize that where we live on the Central Coast is one of the most beautiful places in the world, and we’re very fortunate to live here.” 

They now think of their island adventure as a priceless, once-in-a-lifetime experience that they can proudly cross off their bucket list. 

“I think that by living out your dreams and going and actually doing something that you thought about doing, you learn a lot about yourself and about life,” Katie summarizes. “This has been a life-long dream for Tyson, and I tagged along for fun, and it was a good adventure. Not many people can say they lived in the Virgin Islands!”  

Contact the Haywards for advice about smooth sailing—whether in the Caribbean, Paso Robles wine country, or the world of homeowning—at or

Jamie Relth - local writer and photographer