When guests book a Virgin Islands charter trip with Island Roots Charters, the heart and soul of the excursion is in the person steering. Nowhere is that more true than with Captain Max. He is known for his warmth, skill, and love for these islands. Captain Max possesses a rare ability to transform an otherwise ordinary day on the Caribbean sea into memories our guests cherish for a lifetime.

Image: Captain Max / Credit: Island Roots Charters

A Captain’s Origin Story

Captain Max's story with Island Roots began with a tent, of all things. If you think about it, the best captains would be the ones who would rather camp than stay in a hotel.

Being Island Roots’ owner Jason Siska’s cousin, an 18 year old Max came to visit Jason in St. John the summer between high school and college. On that visit he pitched a tent in the yard and spent all summer living the island life of fishing and boating nearly everyday. This was a life he had only dreamed about back home in the Chicagoland area.

Max kept coming back every summer after that, even during college at Ole Miss.

Summers started becoming more than sunshine, fish, and salt water when Max began working diligently toward his USCG License. He learned about the sea, the boats, and the business of being a great captain from the ground up.

He officially joined the Island Roots team in 2021 and began living full-time on St. John. It wasn’t long before Max met the love of his life who he married a year ago, with the ceremony taking place here, on-island.

A Day on the Water with Captain Max

We get a lot of wonderful feedback and reviews about our captains, but every so often one comes along that captures exactly why guests fall in love with their Island Roots charter experiences, and the captain that made it possible. Here are the quotes from a letter below from June 27, 2026 that demonstrates the experience and passion Captain Max brings to every one of his charter trips:

“I want to thank Island Roots, you, and Capt. Max for such a terrific day with him from which we will have fond family memories forever! He is a superb captain and was so kind to us. We went all over the place, being introduced to new sights along the way to which we hadn't previously gone and caring for us through going beyond my comfort zone with regard to speed, choppy seas, making sure we got as close as possible at The Baths drop off point in Devil's Bay, patiently waiting for us to return from visiting there, from breakfast on Jost at his recommended Tipsy Shark and meeting Foxy, and lunch and snorkeling at Pirate's Bight [one of our favorite lunch stops], and helping my daughter and I while onboard through an unexpected rough wake, making sure she was safe because she wasn't awake and aware.
He taught us about the islands, both above and under the water and we, by far, experienced the clearest and most beautiful snorkeling there that we'd had in that spot. He even managed to fulfill our older daughter's hope of seeing an octopus before we left, after explaining what to look for and she found one!
I can't always get comfortable on the water in a powerboat but he somehow managed to calm my fears after a while. It was really evident that he is an excellent navigator through the waters and just loves the islands and boating. He talked fondly of his family and you all run a great business with regard to experience, great equipment, really listening to your customers to customize a trip for the experience desired, and communicating well beforehand.

When you’re ready for your own charter boat trip with one of the best captains in the Virgin Islands, be sure to request Captain Max.

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