"When I walk out onstage every night, that's how it feels: like a big get-together where I come from!" the country star tells PEOPLE exclusively

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As No Shoes Nation knows, there’s something extra special about a summer night spent at a Kenny Chesney concert.

The clearest illustration of that island vibe may be perfectly captured on the above live video of the country star’s hit “Pirate Flag,” premiering exclusively on PEOPLE. This particular rendition of the track will be featured on the Chesney’s upcoming album, Live in No Shoes Nation. It’s one of 30 songs on the double disc set of Chesney’s personal favorite live performances, out Friday.

When picking which live performances to include on the album, Chesney had some “simple” criteria: “magic.”

“Some of these tracks — you just hear it,” the star, 49, tells PEOPLE. “For me, when I started listening to the tapes, what struck me — and stayed with me — was how much passion [my fanbase] No Shoes Nation really has. These people come year after year. They live these songs every single day, and you can tell when you hear them sing — or look in their eyes — that they know what these songs are about, where they came from.”

Kenny ChesneyLive in No Shoes Nation album

His fans’ passion for and embrace of the music fuels him, Chesney says, calling it “unbelievable.”

“That’s what makes these performances — even the quiet ones like ‘One Step Up’ from the Stone Pony, ‘You and Tequila’ or ‘Happy on the Hey Now,’ from a very special Gillette Stadium show — stand out.”

The album features a number of special guests — from Taylor Swift to Eric Church to Grace Potter to Dave Matthews.

“She’s such a special artist — she’s my go-to secret weapon,” Chesney tells PEOPLE of Potter while reminiscing about a 2011 performance of their duet “You and Tequila” at the famed Red Rocks Amphitheatre.

Credit: Jason Kempin/WireImage

“The song is a special song,” Chesney says. “Grace is a special singer, who really understands how to find that innocence in the wreckage. She’s powerful, but she’s strong in the soft parts — and that dreamy tone is the way you feel when you’re losing the battle with something you know isn’t good for you, but it’s got a hold on you.”

And onstage, that specialness really shines. Says Chesney, “Grace brings more than her talent to the stage; she brings this beautiful energy that’s so contagious to everybody that’s around her.”

Kenny ChesneyCredit: Allister Ann
Credit: Allister Ann

While Chesney still can’t believe that he’s had the chance to play major stadiums and arenas to crowds of thousands, he’s happy to have established a fanbase of “people who lived life with a lot of passion, who worked hard and had fun hard, loved where they were.”

And that’s why the star feels a kinship to them: “When I walk out onstage every night, that’s how it feels: like a big get-together where I come from! It’s a party, but it’s so much more. It’s celebrating how we all live and love and just come together. It’s why NSN is the best group of people I’ve ever met – and I’m so glad they love my music.”

Kenny ChesneyCredit: Allister Ann
Credit: Allister Ann

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Chesney’s Live in No Shoes Nation is out Friday.