Flyaway Charters

WELCOME TO THE TEAM CAPTAIN IVAN! We are THRILLED to have this stellar captain as a part of our team! Check out more about Captain Ivan and his love for the water and experience:

Originally from Vermont, Capt. Ivan grew up sailing on Lake Champlain and making annual trips to the coast of Maine where he developed an early love for classic sailing yachts and watercraft.

Ivan arrived on St. John in 2012 for what was supposed to be a 6-month working vacation from his life in Portland, Oregon, he immediately fell in love with the natural beauty of the island and the sea both above and below surface. Having never seen tropical water before Ivan quickly becoming an avid SCUBA and Free Diver. Shortly thereafter and particularly in the wake of Hurricane Irma he became more involved with the wider community of St. John and developed a keen interest in the History of the Virgin Islands.

Throughout his time on St. John Ivan has worked on and near the sea as Jet Ski Tour guide, Sailing Instructor and Watersports Concierge before cutting his teeth as a professional crew aboard larger “cattle boat” charters where he developed his passion for top notch service with an emphasis on safety.

As a Captain Ivan has operated vessels large and small before settling in as a Freelance Captain for some of the premier Private Charter operators in the VI. Ivan might hold a record for most different boats operated in a single season. Captain Ivan is excited to join the team at FlyAway Charters with a shared commitment to delivering the absolute best day of your vacation.

As your Captain Ivan will work hard to cater the day exactly to your interests. Whether you’re hoping to snorkel the best spots, sightsee and hear the told and untold stories of the VI, enjoy drinks, get way off the beaten path, or “do it all” while cruising in safety and comfort Ivan looks forward to welcoming you aboard.

In off time Ivan can be found trying to keep up with his 4 year old son Joah who is lately an avid cyclist and jigsaw puzzle and LEGO enthusiast.

Booked your St. John trip? Don’t leave without doing this 🇻🇮➡️🇻🇬

One boat ride and you’re island-hopping between two countries — clear blue water, no crowds, and views you can’t get from land.
Half-day, full-day, and sunset charters departing St. John, straight to the BVI.

📍 Departing from St. John | USVI → BVI
Save this for your next trip 📌

caribbeanvacation

Thank you, Ivan, for all the joy and memories. Rest easy. 🌴

Ivan’s passing has me thinking about how much joy he brought to these islands. 🤍

I remember a trip to Ivan’s twenty years ago, aboard my dad’s charter boat — the music, the sun, the easy laughter. He’d belt out that Kenny Chesney tune like it was written just for us. Walking into Ivan’s always felt like walking into home.

That warmth he had, the way he made everyone feel welcome, is what we try to carry at FlyAway charters aboard Picaroon’s Parlay, making room for your stories and smiles.

We hold that with joy and gratitude. So come on down this year and let’s make some memories that you can’t get enough of. 🌅🧡 - Leah

Underneath it all.🤿 St. John’s reefs are alive in ways you have to see to believe — and we’ll take you straight to the spots only accessible by boat.

— one of our favorite spots in the BVI to dock and stay for a while.📍We’ve got a few dates open this month if you want to see it for yourself. Book direct with us at the link in bio.

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This is what a day with FlyAway feels like. ☀️

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From first jumps to lifelong memories—there’s nothing like a day on the water with FlyAway 💙

Book your charter at the link in bio.

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From first jumps to lifelong memories, there’s nothing like a day on the water. 💙

Book your charter at the link in bio.

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Golden hour has a way of finding you out here. Some afternoons are just better on the water.