The Inside Scoop on Kenny Chesney’s “Knowing You” Video

The Inside Scoop on Kenny Chesney’s “Knowing You” Video

Good Morning!  Kenny Chesney released his “Knowing You” music video today and I wanted to share a bit about the people, and the boat, involved in this video….The following is a sneak peek into a more in depth, upcoming interview with the video cast and sailing crew aboard the featured vessel, Kai.

Last summer, my boyfriend Teddy and I were invited to sail north from Puerto Rico to Connecticut on the amazingly beautiful sailing vessel, Kai.  Captain Justin Smith and First Mate Sarah Ford are long time friends of Teddy’s and had extended to him their need for company, and experienced sailors, to assist on this 1500 nautical mile voyage in July.

The Inside Scoop on Kenny Chesney's "Knowing You" Video 1
The crew of Charter Kai prepares to sail north from Puerto Rico with the boat, prior to the new paint job, in the background.

In the early months of the pandemic and with a desperation to see my family, we discussed it and I agreed to also come along (Although I AM NOT an experienced sailor. Ha!).  So, we sailed Teddy’s boat Asante to Puerto Rico in early July to meet up with Kai and her crew and make ready for the 8-12 day off-shore voyage.  It was one of the most nerve wracking, and best, decisions I have ever made.  The sail north was fair winds and beautiful seas filled with dolphins and whales, sunrises and sunsets, and millions of memories.

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Sunrise from the cockpit of Kai, somewhere in the middle of the Atlantic.

After four months in a marina in Connecticut and a boatyard in Gloucester, the beautiful sailboat with a brand new paint job made its way back to the territory on a grueling, into the wind journey through the outer bands of Hurricane Eta.  But they pushed on, knowing they had a schedule to keep.  Just before the crew left the states, they received a call that Kenny would be shooting his next music video on St. Croix mid-November.  And he was looking for a sailboat.

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Kenny and co-star, Monica Knaggs, aboard Charter Kai in St. Croix- Photo Courtesy of Allister Ann

The video was partially shot in Gloucester.  Coincidental, because Kai had been in the boatyard getting an incredible facelift in that same little quaint New England fishing town during the month of September.

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Kai leaving the boatyard in Gloucester late September with new paint that was ready to shine!

The other half of the video was shot in St. Croix, much of it aboard Kai with a co-star that is a long time resident of St. John.  And, a beautiful face that you may recognize if you have frequented some dining establishments in Love City.

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Kenny and Monica, during the shoot on the bow of Kai- Photo Courtesy of Allister Ann

For now, I’ll leave you to viewing this latest release from a guy who sings tales about this little rock that we call home and donated millions of dollars and man hours to the response and recovery of St. John after Irma.  But, next week, I’ll be doing a sit down with the cast and crew from the video on Sailing Vessel Kai.  So, enjoy the video and check back in about a week for some insider sneak peeks about the boat and working with Kenny!


21 thoughts on “The Inside Scoop on Kenny Chesney’s “Knowing You” Video”

  1. To sail the seas with friends and family. Nothing like it. I have so many Knowing you ocean moments, I would trade.

  2. This is awesome!! Thank you so much for posting this on NewsofStJohn! Looking forward to upcoming news!

  3. Beautiful… I took time at work today to watch the MV; & parts of the MV reminded me of our marriage – 27th wedding anniversary (plus an additional 13) today… it moved me in a special way… thank you, Kenny and avid fans alike… ❤️

  4. What a wonderful story! Thanks for sharing! My love for Kenny, his music, and St John runs deep! This video is definitely one of my favorites from him!

  5. My close friend and neighbor just died from cancer and this song just struck a chord with me (so to speak), made me sob like a baby!

  6. I listen to NSR frequently. Ok, most ever day. And I have been trying to get to St. John since April, 2020. My two friends and I had a 12 day trip planned which included 5 days on a Moorings catamaran and 5 days based at a villa on St. John. We moved the trip to April of 2021 and then again to April of 2022. I watched the video when it came out last week. Wonderful imagery to match the mood and poetry of the song. And now I see this article. I won’t wish time away. So, I choose to savor every day that I am able to anticipate our trip in April 2022 and will continue to listen to NSR and check in with “News of St. John”. Thank you. See you soon!

  7. Love this video. I have watched it at least a dozen times and not just because my sweet, beautiful niece, Monica is in it. The scenary is amazing.

  8. This video captures the beauty of Gloucester..My husband grew up in the Eastern Point Lighthouse and his love for that place runs so so deep. His parents actually lived on Thatcher’s Island for some time too…My huband’s father was in the Coast Guard and was the lighthouse keeper to both…How cool is that??? To see this video reminds just how much I love HOME and want to keep her from becoming like every other place…She is perfect the way she is….. Kenny Chesney must see something really special in her too! Thank you Kenny Chesney for capturing a glimpse of Gloucester’s natural beauty to share with “no shoes nation”….:)

  9. Love me some Kenny… I’m just an old (66) East TN boy from Chuckey,TN. Kenny used to play at the Chuckey Trading Co. while he was in College (ETSU). I’m an ETSU alumni as well; 1985. My best friend and I were fortunate to have spent 31 days on St John in 1983. We stayed in Cinnamon Bay Campground for two weeks and then stayed on a sailboat moored up in Cruz Bay. This was all prior to Kenny’s upcoming fame. I’m now a NSR Radio fanatic and every single day I relate several songs to my stay in St John. One of these days I hope to get back and re-live some of those great days… maybe look up Kenny! Love to all and cherish every day!

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