Shanna Dickerson

Shanna Dickerson is the founder of Blue Sky Luxury Travels, offering high end rental villas, yacht charters, private islands and private jet service.

From grocery deliveries to a global luxury travel company, Shanna Dickerson has certainly come a long way with her company Blue Skies Luxury Travels. Booking private villas, private islands and yacht charters, Dickerson now takes to the skies to offer luxury air travel through a new partnership with Magellan Jets.

Originally from Charlotte, N.C., Dickerson graduated from UNC Wilmington in 2001 with a degree in communication. Working for Clear Channel Entertainment in concert, festival and corporate event promotion and production, she helped produce concerts by names such as Rolling Stones, Fleetwood Mac, Kenny Chesney, Jay Z, The Police, Pearl Jam, Jimmy Buffett, Snoop Dogg, Stevie Wonder, Kayne West, Foo Fighters, Metallica and Tim McGraw. In 2004, at the age of 25, she became the tour manager for the legendary Steve Winwood.

Dickerson had always dreamed of moving to the Virgin Islands, where her family often vacationed as she was growing up. After 10 years in the music business, Dickerson had a decision to make. She could go after her dream now and figure out her work situation, or she could stay in the music business and corporate America and move down to the islands in 40 years to retire.

In 2010, realizing Kenny Chesney had a house on St. John, she reached out to contacts in his management team to see if he had any referrals she could use to move down and start a business.

The first contact she was given was Jack Andrews, a developer in Peter Bay. Andrews offered her a live-in property management position at the Peter Bay Beach House, so she downsized to two suitcases, sold everything and moved to St. John.

At Peter Bay Beach House, which was renting for $20,000 for the week, Dickerson was dealing with extremely affluent travelers, getting their groceries, planning itineraries, hiring chefs and planning activities. She decided to start her own company delivering groceries to villas on St. John for arriving clients.

The business boomed because of a forgotten lime. One day, she forgot the lime on a shopping list for a client and went all the way back to the store to get one and deliver it.

The extra effort was noticed by a large luxury vacation villa company, who offered her the provisioning business for 400 villas. She made a deal with Starfish Market and got her liquor license to buy wholesale and sell retail out of her car.

“I was in all of these villas and I was seeing them firsthand, and I realized that getting a percentage for booking a villa for $20,000 a week and the concierge business is really the way to go,” Dickerson said. “So that’s how I got started. I started to balloon out with the charters and private islands and now private jets. Now Blue Sky is a global multimillion dollar business.” It wasn’t all smooth sailing for Dickerson. Business came to an abrupt halt after hurricanes Irma and Maria in 2017. The major share of her business was on St. John and in the BVI, which were badly damaged from the storms. She had no income for three months, and spent that time making contacts on other islands. She decided to go all in and withdraw her entire 401K to try and grow the business.

“I swear it got down to the very last cent before things started to take off again for me,” she said. “I used that money to go to every island that was still standing. It made sense for all my high-end clientele. Turks and Caicos, Belize, Antigua St. Lucia, Anguilla, St. Kitts, Nevis, you name it, I was on a flight trying to expand the business as quick as possible.”

With more islands in her portfolio, Blue Sky was now able to offer other options in the Caribbean for her clients while the Virgin Islands rebuilt.

At the same time, the USVI and Puerto Rico were awarded $6 million from FEMA in emergency funds, and thousands of construction workers and supervisors were coming to the islands looking for temporary housing since most major hotels were destroyed. Dickerson formed another company, Blue Sky Global Logistics, working with FEMA, the Coast Guard and 11 different construction companies to find housing for their employees.

Almost three years later, the COVID-19 pandemic hit, again limiting travel, but in the end, that eventually turned to Dickerson’s advantage. Booking private villas, private yacht charters and private islands that are safer and more isolated from the pandemic Blue Sky was already set up for that type of traveler. As many companies decided to cut back on marketing, Dickerson did the opposite. She doubled her marketing budget, making sure Blue Sky was a constant presence on Facebook, Instagram, YouTube and LinkedIn. When travel resumed, the gamble paid off, Dickerson said, and the travel business has actually grown by 1,100 percent.

“I think it’s important for businesses and entrepreneurs to be able to pivot,” she said. “One of the most important things I learned is just to really trust my intuition. I didn’t see this vision in 2010. You have to keep your eyes open and pay attention, because what you think is your business could do a total 180 in a couple of years.”

New for Blue Sky in 2021 is the addition of a partnership with Magellan Jets to offer private air travel to and from the luxury accommodations Blue Sky offers.

“I love their safety ratings. That’s hugely important to me,” said Dickerson. “Their staff is incredible and their three owners are great. Everything fell into place with this company, and it came at the perfect time because with COVID-19, more of my clients are interested in private air travel. So again, COVID-19 has been another pivot that has expanded my business.”

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