The video for Kenny Chesney’s latest single “Pirate Flag” made its debut this morning on The Boot.

Directed by Shaun Silva, the “Pirate Flag” video shows Kenny pulling what he humorously likens to a “Ferris Bueller” move. Leaving work behind, he’s having a blast in the Caribbean — swimming, sail-boarding, and rocking out on the beach. The singer’s beloved old blue chair even makes a cameo appearance … in a bit of an unexpected place!

The multi-platinum-selling musician’s co-stars in the clip are some of the most beautiful video vixens in country music — and aren’t just pretty faces hired by casting agents. These “long-legged models” are actually the singer’s friends. “Those are girls I know from the island who did the very thing this song is about,” Kenny explains, “and that freedom from what’s expected just makes them shine.”

Watch it below: