Island Roots Set to Sail Again

Island Roots Logo

Nearly three months have passed since Captain John Stewart lost his battle with cancer, but soon his beloved catamaran will sail once again, and it will be captained by a man with true “island roots.”

Jason Wilder Siska first met Captain John Stewart two years ago over at Miss Lucy’s in Coral Bay. After that initial introduction, the two found themselves bumping into one another around town – both lived in Coral Bay – and also out on the water – Captain John was frequently out chartering Island Roots while Jason worked at Ocean Runner. Together they’d chat about their love of St. John, what they pictured for the future of Coral Bay and, of course, their shared interest of being out on the water.

“He once said, ‘Jason, a Virgin Islands charter boat captain is the best job in the world,'” Jason recalled earlier this week.

Captain John quickly took a liking to Jason, so when he was diagnosed with pancreatic cancer earlier this year and had to leave the island for treatment, he asked Jason to step in and help.

“John contacted me about running a few charters for him and to get a feel of the boat to see if I’d be interested in purchasing the boat and company,” Jason said. “I’d been in the process of starting my own business from the ground up and when this opportunity came along, it seemed the right choice. John took really good care of the boat and the engines, and I knew I wouldn’t be getting a ‘lemon.’ The business also had a great name – Island Roots – a small coincidence since I was born on St. John and my ‘roots’ are actually here.”

After a bit of discussion, the men finalized the sale just days before Captain John’s passing on June 30. It was a decision that Erica Stewart said her father was at peace with.

“I can say that he felt very comfortable entrusting Jason with the boat and the reputation of Island Roots, which he worked so hard to build,” Erica Stewart said. “My dad described him as the kind of guy that lights up a room when he enters. And that he had the expertise and enthusiasm to run the business the right way.”

Captain John even boasted about Jason in an email sent to fellow boat captain John Brandi, of Palm Tree Charters, just before his passing.

Island Roots Set to Sail Again 1
Captain John Stewart

“I really like what I know about him, even though he is not old like me and some other captains,” John wrote in an email according to Erica Stewart. “He did promise to change his name to Captain John so that is definitely a plus. Why, I feel better already!

Jason, who may or may not be changing his name to John, is eager to continue Captain John’s legacy when he sets out on the first charter of Island Roots’ next chapter on October 14.

“I’m very excited to be taking the wonderful small business that John worked very hard to create,” Jason said. “Going through his journals and financial records of Island Roots, I saw firsthand how difficult it was to start at the ground up. I felt honored that John contacted me in regards to the business and can only hope that I make him proud in continuing to offer a unique and memorable experience for Island Roots guests.”

Jason Wilder Siska
Jason Wilder Siska

Jason is no stranger to the waters around St. John, so we’re pretty certain he’ll do a great job. Jason was born at the Myrah Keating Smith Community Health Center in 1985 and spent his childhood living in Johns Folly. He attended Guy Benjamin School until his parents relocated to the states when he was 10 years old. Jason lived in Chicago until 2008 when he graduated college with a teaching degree and soon found himself back on the island where he began teaching History and Spanish at Gifft Hill School.

He taught for three years before deciding a career change was in order. He left to work as a dive instructor and boat captain, something he describes at the “best life change ever.”

Oh and there was a little something else that occurred around 2008 – Jason appeared as a contestant on Survivor Micronesia: Fans vs. Favorites. He did pretty well on the season, lasting 30 out of 39 days; however his luck ran out when he chose not to play an idol at Tribal Council. “I was voted out because of my youthful naivety in trusting some people I shouldn’t have,” Jason said.

“During the auditioning process, I always joked that Survivor was going to be ‘just another day at the beach,’ kinda like a Sunday afternoon at Cinnamon Bay. Boy, was I wrong. (It) was one of the toughest mental, physical and spiritual experiences of my life,” Jason said. “I know everybody says that, but that’s because it is.”

Jason said he’d go back on the show in a heartbeat, but in the meantime, his focus is on Island Roots. His plan is to show guests the beauty of St. John and the surrounding islands, more so than traveling the typical charter route over to the British Virgin Islands.

“In the 2011-2012 season, only 18 percent of Island Roots charters stayed in local U.S. waters.  The other 82 percent traveled into the BVI. Mind you, I love the BVIs and all the cool places to go, and for some visitors to the island, it is the best day of their vacation. But I also think that because there’s all this hype about the BVI, some families and groups who might be more interested in further exploring the beauty of St. Johns shorelines are sometimes misguided by that hype.

“Additionally, the more budget-minded traveler might also like to know they can save a significant amount of money by staying in local waters.  Save on fuel as you don’t have to travel so far … Save on the $35 per person customs fees … You’re also saving on time as you don’t have to deal with checking in and out of BVI and US customs. I guess what I’d like to do is let people know that if they want to snorkel, St. John has the best!  If they want lunch and cocktails at a beautiful shoreline restaurant, St. John has it – Miss Lucy’s, Vie’s, Shipwreck, The Beach Bar, Hull Bay Hideaway. If they want a floating bar, St. John has it,” Jason said referring to Angel’s Rest.

If you’re interested in learning more about Jason and Island Roots Charters, you can visit their Facebook page by clicking here.

Lastly, the Stewart Family is planning an island celebration of Captain John’s life later this year. Please click this link for more information.

4 thoughts on “Island Roots Set to Sail Again”

  1. Cool story. From the sounds of it I think this will all work out just fine for Jason. But I like how he slipped a little STT in there with Hull Bay Hideaway. Does Island Roots “headquarter” out of STT or STJ?

  2. What a beautiful story and I know that Jason, Captain John (RIP) has made a terrific choice!! Good Luck and we will see you soon!!
    No better Captain in US waters
    All the best

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