meet the Team

Owner // Operator
USCG Licensed Captain

Jason’s Island Favorites

Snorkel: When sea conditions are right, one of my personal favorites is a long drift snorkel along the Southern shore of Congo Cay towards the Western point.

Hike: Sunrise walks to Drunk Bay and exploring the tide pools at Nanny Point with our son.

Eat: We typically eat at home as a family but when I want to “wine and dine,” The Terrace is where you’ll likely find me.

Drink: I much prefer a cold one on the boat at the end of the day to any bar.

Beach: Our “backyard beach” at Salt Pond! It’s only a 8 minute walk from my front porch, is consistently calm, and gets full sun all year round.

Island Fun: My idea of fun probably differs from most. To me, nothing beats a day spent in the yard landscaping, mixing dirt, spreading mulch, stacking boulders and working on my backhoe.

View: The almost surreal view from “Picture Point” on top of Bordeaux Mountain is my favorite. Don’t forget your sweatshirt though…the windchill and elevation make it cold up there!

Beginnings: Being a contestant on Survivor: Micronesia — Fans vs. Favorites (16th season, 2008) inspires Island Roots Charters in many ways today. Jason Siska now continues the game as a guide for others who want to step out of the world of reality TV and embark on their own real life adventures here in the Virgin Islands.

Owner // Office Manager

Jill’s Island Favorites

Snorkel: I find snorkeling the mangroves in Hurricane Hole pretty fascinating. They act as the ocean’s nursery! If you look closely you’ll find all types of juvenile fish, lobsters, sponges, anemones and baby barracudas hidden among the elaborate root system.

Hike: Hiking through Reef Bay after rainy season is pretty special! I love how dense and green the foliage is then. Plus, if you’re lucky there will be a waterfall over the petroglyphs.

Eat: La Tapa! La Tapa! La Tapa! Hands down my favorite for a girl’s night or a date night.

Beach: Hmmm. . . all of them!

Drink: My favorite bar has evolved over the years. Back in the day it used to be The Beach Bar or Quiet Mon but now I much more enjoy a freshly made margarita on my porch with friends.

Island Fun: When I have a day off from work and mom duties my kind of fun would be reading good book at the beach…alone.

View: Those blue and green vistas are gorgeous but there’s something to be said for a crystal clear Caribbean night sky during a new moon.

USCG Licensed Captain

Ryan’s Island Favorites

Snorkel: Reef Bay! Although I’m usually stuck behind the helm, I get the most consistent positive feedback from guests when conditions allow us to visit.

Hike: We like to do family hikes with our 5 year old, and the Francis Bay boardwalk is our favorite. It’s not too long, and there is nice variety between plant life, migratory birds in the salt pond, and fiddler crabs in the marsh.

Eat: 1864 is my favorite, but I am biased ;)

Drink: I love the outdoor atmosphere at Windmill Bar.

Beach: We usually pick a beach based on the sea conditions of the day, but Maho is wonderful in the early morning and late afternoon.

Island Fun: I love beach days with other families, where the kiddos get to run and play together.

View: My favorite is the view from atop Caneel Hill. It’s a grueling 1 mile hike with about 800ft elevation gain, but a stunning vista awaits at the top.

USCG Licensed Captain

Max’s Island Favorites

Snorkel: Eagle Shoal is by far my favorite. It has the most beautiful reef around but can only be accessed by boat on a super calm day.

Hike: Rams Head has some amazing views for sunrise, sunset, and the full moon!

Eat: My Aunt Jill’s kitchen! She is one of the best cooks. But outside of the home, Morgan’s Mango is one of the better spots to get fresh seafood.

Drink: I have a couple fun bar favorites you might find me at. I like to hit up Beach Bar for some live music and Drink! has some great vibes and cocktails.

Beach: Cinnamon Bay all the way! I spend most of my free time at Cinnamon surfing, foiling, cracking a cold one or just enjoying the beach.

Island Fun: Even when I am not working on Roots, I still tend to find myself on the water every day. I spend most of my free time fishing, spear fishing, free diving, scuba diving, surfing, or foiling.

View: Bordeaux mountain! Looking out you can see the south side of St. John, East End, and almost all of the BVI’s.