Menu Close

Island Roots Boat Charters: New Offerings & Discounted Rates

Boat days are the best days. We know there are a lot of options out there when booking a day on the sea, so today I’d like to introduce you to a family-owned company that’s truly rooted in the sea – Island Roots Boat Charters.

Island Roots is owned by Jason and Jill Siska, and their adorable four-year-old son Finn. Captain Jason knows the Virgin Islands and its waters well, as he was born and raised on St. John through his early childhood. He returned to the island after college and soon met Jill, a 20+ year island resident.

Jill, Finn & Jason Siska

Jason and Jill purchased Island Roots from the late Captain John Stewart in 2012. Together they built Island Roots into one of the island’s top charter companies. Island Roots is consistently ranked one of the top ten outdoor activities in the US Virgin Islands.

“We are truly a family-owned business,” Jill told me recently. “It’s just me and Jason doing this. Island Roots was built over years and years of hard work. Over that time, we’ve been educators, firefighters, first responders, and involved community members. We are choosing to raise our family here, and we care about St. John.”

The Island Roots fleet consists of three 32′ World Cat power catamarans. Each is built for maximum comfort, and a smooth, stable ride. Island Roots offers full-day trips in both the US Virgin Islands and the British Virgin Islands, as well as local sunset trips. Extended trips are offered to those who want a little extra time over in the BVI.

Island Roots’ New Offerings

As you all likely know, numerous restaurants close for the off-season, including many of our water-based spots like Lime Out and Pizza Pi. As a result, Island Roots will focus exclusively on snorkeling and exploring the island’s outlying cays, bays, and beaches that are only accessible by boat. In doing so, they are now offering two four-hour, USVI boat charters. Whether you opt for the morning (8:30 a.m. – 12:30 p.m.) or the afternoon (1 p.m. to 5 p.m.) session, you’ll have time to make three to five distinct stops during your trip. Despite the shorter trip, you will still have plenty of time to swim, snorkel, sightsee, cocktail, cruise, and explore!

Explore lesser-known spots with Island Roots Boat Charters.
Island Roots’ fleet is spacious & comfortable.
Island Roots can accommodate up to 24 guests on tandem trips.

Discounted Rates through October 15th

Island Roots will continue offering its full-day USVI and BVI trips, as well as its extended BVI trips and USVI sunset sails throughout the off-season. All trips will be discounted 10 percent from August 27th through October 15th.

All of Island Roots’ private boat charters are unique and customized to the interests of their guests – from birdwatchers to sunbathers, snorkelers, photographers, free-divers, cocktail connoisseurs, food enthusiasts, and folks seeking the ‘best of’ the islands to casual-fun-boaters looking to just enjoy the breeze and some time on the water.

Snorkel St. John’s beautiful mangroves on a US trip.
Explore the Baths on Virgin Gorda on a BVI trip.
Grab some friends & jump off the Willy T in Norman Island.
Visit the Caribbean’s only floating taco bar in Coral Bay.

Island Roots provides its guests with professional-grade snorkeling equipment, as well as snorkel belts, pool noodles, mask defogger, fish identification books, and other water toys. Each boat has a freshwater rinse and comes with a cooler stocked with ice and water.

Ready to get out on the water? Ready to save some money? Ready to see something new? You can learn more about Island Roots Charters at or by calling/texting 340-643-5000. You can also check them out on Facebook at and on Instagram at I hope to SEA you all out there!

Related Posts

1 Comment

  1. Tammy

    I like that Island Roots is a family business. Looks awesome. We are coming to St John June 1st 2024. We have been looking into a visit to the BVI. I may contact you for information and rates.

Leave a Reply

Your email address will not be published. Required fields are marked *