Shanna Dickerson on Taking Risks & Embracing the ‘First Class’ Beach Life on 30A – 30A

Shanna Dickerson on Taking Risks & Embracing the ‘First Class’ Beach Life on 30A

In this edition of 30A Q&A, we caught up with Shanna Dickerson, Chief Experience Officer at Blue Sky Luxury Travels, who recently made 30A her new home.

1. You live in the Caribbean? What’s that like?

I live about half the year in the Caribbean and the other half at my home in the States, which as of a month ago is 30A! Before Coronavirus, I was expanding the company to much farther destinations such as Fiji, Hawaii, and The Mediterranean, but now that there are so many travel restrictions, I have been sticking to St. John in the US Virgin Islands (our top destination at Blue Sky).  The Virgin Islands first came into my life about 30 years ago. I’m from Charlotte, North Carolina, and there is a direct flight to St. Thomas USVI so we vacationed on St. John often. I loved our island trips so much that I would always get depressed when we would leave. So finally in 2010, at 30 years old, after 10 years in the music business in Nashville, Tennessee, I decided to sell everything, downsize into a few suitcases, grabbed my yellow lab Dakota and we took a one-way flight to St. John USVI. I started a company from scratch, on an island of 19 square miles with 4,000 people, in the middle of nowhere, knowing hardly anyone there, with barely any money in the bank because I spent it on this big relocation. Very few people in my life supported my decision, but it’s a good thing I listen to my intuition over other people’s opinions.

To say this was challenging would be an understatement. But fast forward to now, knowing all of the major hurdles I’ve had to endure, I would say it was the BEST decision I have ever made. This way, I’m living out my dream life at 40 years old versus 65 years old. Being able to bounce around the Caribbean half of the year is as good as it gets! It’s where I feel the most at home. The beauty of St. John USVI is unmatched. And with 800 rental villas, excellent restaurants, fun activities, and the fact that it’s very safe, this tiny island in the Caribbean will always be my #1 go-to and the top destination of my company.

2. When did you first visit 30A?

I lived in Nashville for 10 years so 30A was the closest beach to us. Over the years, I had been down a handful of times and really considered moving here in 2010, but I choose St. John USVI instead. Then when we filmed my TV pilot World Class, we chose 30A to be the destination we spotlighted.



That pilot made me fall in love with this area all over again. It has a St. John feel to me.

We are still looking for a network to call home.



3. What made you decide to move here?

Since I’m a Caribbean lover, 30A is the closest thing to that lifestyle while still being in the continental U.S.  As much as enjoy my life in the Caribbean, it comes with its own set of challenges so I like mixing it up. The clear, beautiful, emerald waters next to the white quartz sand are so stunning! Plus I like the 18 miles of bike path along 30A. Jumping on a 30A electric bike by YOLO and stopping beach town to beach town is one of the most fun activities. The restaurants are excellent, and so is the shopping. And the community here is full of genuine, kind-hearted people. 30A is a very special place. I’m excited to be expanding my travel business here. I think it’s going to be a successful destination for us.

4. So far, what are some of your favorite places and activities here?

My favorite hobby is tennis. I’ve been playing for 30 years and have a 5.0 rating. That being said, I’ve been beating up on the local tennis pros at Alys and Rosemary! But seriously, these courts and pros are excellent so that’s a big plus in my book.

Riding the bike paths on an electric bike is one of my favorite things to do.

I’m not a big shopper, but I have to say I’ve been shopping like crazy here! The local artists are so talented. Plus, paddleboarding the coastal dune lakes is about as magical as it gets.

5. Your business takes you to many exotic destinations around the world. What differentiates 30A from the many other beach destinations you’ve visited?

30A is a tropical paradise and offers a Caribbean-like lifestyle, but it has the uniqueness of being in the United States. Not everyone feels comfortable flying or going to islands in the middle of nowhere so this area in Florida in the Gulf of Mexico is a great option for those. But let’s be real, 30A has its own unique barefoot luxury vibe and I’m just so grateful to call it home!

Are you a 30A local? We’d love to hear from you! Email us a little bit about yourself and we might just feature you in our next 30A Q&A!