Flyaway Charters

💙⚓️ We love Captain Holly!

After being with us part time for over FIVE years, Holly is joining us even more this season—and we couldn’t be happier! 🌊

Originally from Athens, Georgia, Holly traded real estate for life at sea aboard the 160-foot schooner Arabella. Her journey took her through Newport and Martha’s Vineyard before sailing south to host charters throughout the USVI and BVI.

Now an island resident of 18 years and a captain for 12, Holly brings experience on sailing and power vessels, incredible local knowledge, and warm hospitality to every boat day. She cares about safety and the little details, tailoring each trip to her guests—from snorkeling adventures and beach bars to quiet coves and the perfect island lunch. ☀️

A few of Holly’s favorites:

🤿 Snorkeling: The Indians or Horseshoe Reef, Anegada
🍽️ Lunch: Sydney’s Peace and Love, Jost Van D**e, or CocoMaya, Virgin Gorda
⚓️ Anchor & chill: Fallen Jerusalem
🏝️ First-time visitor stop: Sandy Spit
💙 Beach: Spring Bay, Virgin Gorda

Her goal is ours: give you the best possible day on the water and an island experience you’ll remember long after you leave.

Holly, we’re grateful for all these years together and excited for more adventures this season!

👇 Have a favorite Captain Holly experience? Leave her some love and share your story in the comments!

September 2017.
Two weeks before, we were the most optimistic we’d ever been. Just engaged, just put our down payment on Flyaway. So many people here were like that — everyone had the beginnings of something.

Then Irma.
We walked down to the dock the next morning. We only passed a couple of people. One had tossed down a message in a bottle, asking whoever found it to call their family and say they were alive. Another was pale as a sheet, but alive. We were just so relieved to see our friends.

The devastation was unnatural. Nothing prepares you for it. It felt like nuclear war. I called my dad on the sat phone that day, taking my hat off and smoothing my hair over and over, saying “you have no idea what we just went through.” He said, “you have no idea what you just went through.”

Most of our community hadn’t made it down to the dock that first day. By day two, they had. Colin had a massive infection in his knee from diving on our boats, and I was treating it with antibiotics left over from dental surgery. We just kept going.

Day two, a boat came over from St. Croix with supplies. They were looking for their son, who was on the island. We helped them find him, and they gave us what they had. Then more boats started showing up, and we formed chains on the dock, hand to hand.

We lost Buxom completely. She was our boat, our heart, our home. The quilt my mom made me was on board. We still use it every day.

We left three days before Maria on a friend’s boat. St. Croix, then San Juan, and somewhere in there we decided to just get married in my mom’s backyard. I found my dress at a second hand shop while Colin was out buying tools and generators. We still use one of them.

Indigo Grill became the place. They cooked whatever they had, we all ate one meal a day there, and we stayed to talk and drink and be together. Ali’s at Calabash too — music and rest at a time when there wasn’t much of either.

The community carried us through something that lasted years and honestly still isn’t finished. It’s the reason we’re still here. 💙

Captain Thatch is a FIRST GRADER! 💙📚🌴

Our littlest crew member is officially off to first grade at Gifft Hill! If you’ve been adventuring with FlyAway for a while, there’s a pretty good chance you’ve watched Thatch grow up right alongside us — from boat baby to first grader somehow in the blink of an eye.

One of our favorite parts of being a small, family-run St. John business is that our family and FlyAway have always grown together. Here’s to a great year for our favorite little deckhand! ⚓️💙

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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