Our Team


It’s not by coincidence that our team of knowledgeable and experienced local captains spend as much time on the sea as most people do in their “nine-to-five” office. We do it because it’s what we love, what we know, and what we do best!

We’re happy to offer advice on what to look for while snorkeling underwater, point out different aspects of the surrounding natural wonders, spin a story or two about the history and local folklore of the islands, top off the ice in your cold cocktail or just turn up the tunes, kick back, relax and let you enjoy the ride.

Jason Siska

Owner and Operator

Born and raised on the island of St. John, he has spent the better half of his life exploring the surrounding waters. As a 50 Ton USCG licensed captain and a PADI certified dive instructor, Jason has logged countless hours ON and IN the water. His experiences include sailing, cruising, free diving, SCUBA diving, fishing, spear fishing, lobstering and snorkeling. A true renaissance man of the sea, his skills were even put to the test in 2008 as a competitor on the hit reality TV show, SURVIVOR, in Palau, Micronesia. Capt. Jason also serves as a VI Fire Fighter/First Responder and spends his “free time” rebuilding his families home after a total loss during Hurricane IRMA. Not to mention, spending as much time with his new baby, Finn!

Scotty McQuaide

Captain Extraordinaire

A native to the Boston area, he relocated to St. John nearly a decade ago to pursue his love of the ocean and its’ waves. After working under some of the most well respected multi-passenger vessels, he now prefers the customization, flexibility and fun that private day charters offer. Certainly no stranger to our local waters, as Captain Scotty has surfed on or dove beneath more of the Virgin Islands reef system than most might think possible! A licensed 50 ton USCG captain, he is eager to show you the best of the US and British Virgin Islands. His love of the ocean and contagious youthful energy will be sure to guarantee a day worth remembering with Island Roots Charters.

Jill Siska

Crew Chief

School teacher turned Island Roots office manager, Jill prefers to stay behind the scenes. She spends her time handling the business side of things and making sure the “Captain in Training” is thriving.

Finn Siska

Captain in Training

The newest member to join the team, baby Finn arrived last October and can often be found getting his feet wet and cruising the surf at Salt Pond.

We Can’t Wait To Hear From You

To better serve our guests and to help in the booking process, complete this form and we can get back to you within 24 hours regarding your charter inquiry and boat rental. Call for immediate inquiries or questions.

2 + 2 =