Shanna Dickerson began her professional career promoting concerts in Nashville. After nine years of working with some of the music industry’s top acts, a higher calling prompted her to move south to the U.S. Virgin Islands. Today, Shanna has built a luxury travel empire that continues to flourish.
Shanna grew up in Charlotte, North Carolina, and fell in love with the Virgin Islands during family vacations. As a teenage star athlete, Shanna played competitive tennis, learning to combine finesse and power simultaneously. She also learned how to translate these same skills into her business life. Shanna decided not to pursue tennis in college. However, after attending a concert with her boyfriend and getting a close look at the backstage music business, pursuing a career promoting musical artists came next.
Blue Sky Luxury Travels CEO Shanna Dickerson poses on her sofa before managing her growing travel empire. (Blue Sky Luxury Travels/2021)
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After obtaining her degree from UNC Wilmington in 2001, the feisty and fit young graduate moved to Nashville. Shanna worked with some of the most prominent music acts for the next several years, such as Jay Z, Pearl Jam, Jimmy Buffett, Kayne West, and Tim McGraw. It wasn’t long before she managed three Steve Winwood tours. Despite her early success in the music industry, Shanna wanted and needed more.
In 2010, Shanna realized she needed a significant change. She sold most of her belongings, canceled her apartment lease, and moved to St. John with her loyal pup. Knowing that Kenny Chesney owned a home and spent time in the Virgin Islands, she inquired about managing luxury properties. Shanna’s pursuit produced dividends after securing management responsibilities for a multimillion-dollar beachfront villa renting for $20,000 per week.
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Today Shanna is the CEO and owner of Blue Sky Luxury Travels and Blue Sky Global Logistics, offering luxury accommodations and private jet service to high net worth clients. The forever youthful entrepreneur now splits her time between St. John and Florida’s Emerald Coast. Regardless of where Shanna wakes up, she begins with meditation and yoga each day before wearing out local tennis pros by pounding a few hundred tennis balls.
“I love the 30a area and plan to live here for many years, especially now that I’m managing luxury properties here too,” Shanna said during her I-65 to 30a podcast episode at SOWAL House in Rosemary Beach.
Listen as she discusses her career and what elite travelers look for in coastal destinations. If you’re looking for luxury sky services, including private luxury air charters, contact Shanna through her website and follow her on Instagram.