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A Simple Twist of Fate- Behind the Scenes of Kenny Chesney’s “Knowing You” Video (Part 2/3)

A Simple Twist of Fate- Behind the Scenes of Kenny Chesney’s “Knowing You” Video (Part 2/3)

When we left off in Part One of this story, Sailing Vessel Kai and her crew were about to head south from North Carolina in order to sail home to the USVI and meet up with Kenny Chesney and Monica Knaggs for the filming of the famed musician’s “Knowing You” music video.  In this second chapter, Monica and her boyfriend Connor leave St. John for St. Croix with some traveling woes while Kai struggles to make it in one piece to Puerto Rico and then St. Croix in time for production day.

On St. John, Monica juggled a full time work schedule with calls from producers, travel arrangements and mental preparation for what would be her first ever on camera experience.  Kenny’s team arranged for Monica and Connor, to fly to St. Croix via sea plane and stay at the Buccaneer in Christainsted the night before the November 14th shoot.  She recalls the voyage as being a bit chaotic.  If you have ever traveled from St. John, you may understand the “island time” hurdles they had to jump on that particular travel day.

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Monica and Kenny on the deck of Kai, taking a break during Monica’s first video shoot,.

On November 13, Connor and Monica arrived at the people ferry dock in Cruz Bay to catch the 5pm ferry to St. Thomas for their evening flight to St.Croix.  The 5 o clock boat was 35 minutes late to arrive at the dock which pushed them for time in order to make their flight.  At the dock in Red Hook, the couple quickly arranged a private taxi that moved with the speed of a turtle.

“It was SO SLOW,” Monica recalled during our interview in the salon of Kai.  She remembers thinking…”We are going to miss this flight!”

They frantically “booked it” through security, only to find that the flight hadn’t even arrived at St. Thomas by the time they finally arrived at their gate.

“It was a nightmare,” she said.

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Justin, Sarah and Monica talk about their journeys to St. Croix in Kai’s salon

Seated nearby as Monica recalled her travels to St. Croix, Justin, Captain and Owner of Kai, and Sarah, first mate for the journey from North Carolina to St. Croix, slightly smiled with a glance that said “Hold my beer.”

After their departure from Cape Lookout on the morning of November 3, Sailing Vessel Kai and her crew of five experienced a spectacular parting gift.

“It was absolutely beautiful the morning we left,” Sarah remembered out loud.  “Remember that sunrise…?” she trailed off.

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Sunrise at Cape Lookout on departure day. – Photo Credit: Alex Dooley

The first few days of sailing were smooth with 35 knots carrying them at a downwind angle before the winds died out completely, subconsciously predicting a calm before the storm.  After 30 hours of motoring, Justin looked at the satellite and charts.  They were 300 miles to the West of Bermuda and 900 miles from their immediate destination of Fajardo, Puerto Rico.

Justin recalled taking into account all of the weather patterns, distances and advisement from his crew.  He then messaged Monica and Kenny’s producer to see if the timeline had changed at all for the video shoot…Or if it was actually happening at all.

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Taking a photo break during the interview in Christmas Cove aboard Kai

“I didn’t really totally believe that Kenny Chesney was going to be in St. Croix when we got there,” Justin laughed.

“I did!” exclaimed Sarah.  “He IS a professional.”

Justin texted Monica at this nautical crossroads with weather looking not-so-great no matter which way they went.  Should they continue East to Bermuda or turn south to head towards Puerto Rico?

“At one point you and I were talking via satellite tracker,” Justin recalled to Monica.  She nodded.  “I texted you and I was like, ’Is this still on?  Is it still happening?”

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November 7 text from the satellite phone aboard Kai between Justin and Monica

Monica responded that the filming of the “Knowing You” video was indeed set to proceed as scheduled.

“Oh, this is going to be terrible,” the young captain thought to himself as he saw intense storm systems churning on either side of their path south.  Hurricane Eta was smashing the gulf coast at the time and the outer bands were nearing the narrowing path south. Another storm was moving up from the USVI that threatened danger on the trek south.

“I talked to Teddy and I talked to Dooley and I talked to Sarah….And we decided,” Justin recalled.

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Kai’s crew at anchor in chilly North Carolina just before their departure for the USVI- Left to right: Captian Justin Smith, Alex Dooley, Tyler Nance, Ted Jennings, Jr. (Teddy). Photo Courtesy of First Mate, Sarah Ford

Kai was just about to turn south, just as the weather satellite stopped working.

“The crazy thing is, “ Justin told us, “We have satellite weather but it kicks on and off at certain points.  We had it leaving North Carolina until we made our turn.  And that’s when we were sailing blind.”

He knew from viewing the imagery throughout the course of the sail that Hurricane Eta was to the west.  He knew there was a storm coming from the USVI.  In knowing what he did about the previously projected tracks, he believed they would go away from them.  Without satellite weather, he could only navigate based on his previous predictions.

“But it didn’t.  It turned towards us,” he shook his head.

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Hurricane Eta churning in the Gulf with other storm systems moving North to the East of Kai’s path to Puerto Rico

When Kai turned south, Justin believed that he could make the journey in one straight shot.  And they did.  But with unwanted stowaways challenging the crew every step of the way.  Huge seas and whipping winds accompanied Kai and her crew for the next seven days.  Sleeping was nearly impossible.  Cooking a hot meal was an unattainable goal so the crew snacked on sandwiches and MRE’s to sustain their energy levels.  All the while the five sailors were nauseous, exhausted and unknowing of when it would end.

“I was crying,” Sarah remembered.  “It was just SO MUCH for so many days!  It was a hard thing.”

“We’ve put 30,000 miles on this boat over the past four years,” Justin said.  “And this was the most challenging.”

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Looking out from the cockpit of Kai into the Atlantic

And Kai herself was struggling to make the journey…

About half way through this chaotic storm surged venture, Dooley looked at Justin and said “There’s no way that you can push it fast enough to get there in three and a half days.”

Justin recalled, “I’ve got Sarah, I’ve got Teddy, I’ve got Dooley and I’ve got Tyler…Yeah, sure, let’s do this.”

He pulled the whole jib out, got the staysail up and reefed the mains and they started doing 11-12 knots.

“I mean, we were just screaming,” Justin said.

Two hours later, the auto pilot broke.  Intermittently, Justin, Tyler and Teddy were able to rig it up to give them a reprieve from manually steering the ship through the intense conditions.  Because Kai was heeled over so much on one side for so many days, salt water was coming in through the air vents.  It seemed the whole boat was leaking and, eventually, salt water started to seep into their drinking water supply.  The electrical systems flooded, leaving them without AC power.  And everything was wet.

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Justin and Tyler struggling to repair the autopilot while underway.

Charter Kai arrived in Puerto Rican waters late on the evening of November 10 with an exhausted crew, a soaked interior and many, many mechanical and aesthetic issues to fix before the filming of the video.  From the time they dropped anchor in PR, the crew had approximately 60 hours before they would need to move the 6o nautical miles south to St. Croix.  And there was a lot of work to be done.

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The morning of November 11, Kai moved into a slip at Puerto del Rey Marina in Fajardo, Puerto Rico.  Here, Teddy would be retrieving his boat, Asante, that had been strapped down “on the hard” and out of harm’s way for the hurricane season.  Dooley would be flying back to St. Thomas in order to return home to St. John.

I flew into Puerto Rico that afternoon to meet Teddy in order to help bring Asante home later in the week.  When I met my boyfriend and dear friends at the dock in Fajardo, their energy was low and they all wore the signs of exhaustion.  The boat was musty and damp inside. The now crew of three, Justin, Sarah and Tyler, had their work cut out for them over the next day and a half.

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Sailing Vessel Kai in calmer seas

Sarah scrambled to find a shore power cord in order to expedite the drying out of Kai’s interior spaces.  With the electrical systems fried, they couldn’t turn on the air conditioner and fans without one.  She managed to locate someone at the marina with an extra, plugged in and turned on the power to begin the process.  She then headed to the marina’s laundry facilities to wash all of the towels and linens that had soaked up the sea water underway.

Justin and Tyler remained on Kai, working to repair sails, electrical power and the auto pilot.  And to clean the exterior of the boat…At that point, she was in no shape to be a star.  When the three of them set sail on the morning of November 13, they hadn’t had a decent night’s sleep in well over a week.

“That morning was like a wake up and stowaway everything, say goodbyes and head off after being in Puerto Rico going non-stop for a day with no sleep,” Justin recalled.

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The remaining crew on Kai pose with Kenny Chesney on November 14 after finally arriving safely on St. Croix

Due to their exhaustion, when Sarah and Tyler headed to the ship’s deck to “reef the main sail” the job didn’t necessarily get done and the Captain wasn’t paying attention fully.  Tyler raised the sail to the the second reef, which is where you can generally get it by hand and where the winch takes over the job.  Justin tried taking over with the winch multiple times to no avail.  They raised and dropped the sail three times unsuccessfully.

Tired and ready to sleep, the Captain said to drop the sail.  And Kai’s motor carried them the 60 nautical miles to St. Croix while slamming into 20-25 knots the whole time. Once the sail was put away, Tyler and Sarah were both finally able to take a long overdue rest while Justin remained at the helm.  Kai and her worn out crew finally arrived on St. Croix on the evening of November 13, with less than 24 hours to figure out what they thought was a broken sail.

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Kai motoring away from Puerto Rico.

Monica and Connor arrived in Christiansted that evening as well.  The next morning, they got on a power boat that would deliver them to Kai to meet up with the vessel Monica had found via Instagram, the crew who had worked tirelessly to deliver her, an expansive film crew with massive amounts of equipment…And Kenny Chesney.

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5 thoughts on “A Simple Twist of Fate- Behind the Scenes of Kenny Chesney’s “Knowing You” Video (Part 2/3)”

  1. Talk about bravery and wherewithal! Wow. What an adventure. So happy everyone arrived safe albeit exhausted and worn. Makes watching the video even that more special knowing the back story.

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