*Note: Since this interview, Roberta has left Pirate Girl Charters and started Captain Happiness Charters. You can reach her at 340-244-8910
Wednesday Night Sail Boat Races, Coral Bay, St.John
Jen: What are you doing right now?
Roberta: The sun is setting and I’m actually relaxing on my sailboat watching a sailing regatta come in. They’re doing a Wednesday night sailing regatta. So…
“if I stop and blow my horn for you, you’ll be happy.”
Jen: Please go ahead and blow it! Wait, do you mean like blow the conch?
Roberta: Yeah, yeah. You’ll love it.
Jen: Well I brought my conch with me here (to Asheville)! It’s literally right here in front of me on the coffee table. In fact, I’ll blow it at the same time as you.
Roberta: Ok, I’ll let you know when I’m going to blow mine! Probably in about 15 minutes. I’ll give you a warning.
Jen: So tell me what brought you to St.John.
Roberta: Well I had a dear girlfriend that would come to Nevada where I was living for 3 months every year and she came to do massage therapy and pilates with me at my studio and every year for about 5 years she would invite me to come to St.John and visit. I finally did it. When I realized that St. John wasn’t a flat desert and that there were mountains and it was surrounded by water warmer and more beautiful than anything I had ever dreamed of I decided to try it out. I fell in love with the island and the people, I volunteered at Beach to Beach Swim and then came back and house sat before I made my big move. I just fell in love with the island and its people.
Jen: Easy to do.
Roberta: Change of life. I was turning 49 and then I moved here.
Jen: So how long ago was that?
Roberta: It will be 4 years in January that I moved to St.John. And a year ago this month (November 2015) I started Pirate Girl Charters.
Jen: You are the Captain and co-Owner of Pirate Girl Charters. Looking back, can you see a clear path that led you here or was it just a series of random chance encounters?
Roberta: You know when I moved to this island the 2nd time and really decided I was going to live here long term, all I knew was that I wanted to be on the water. I’ve owned boats for years it was a part of my life. I never really thought that I would be doing it for a living, but I started crewing on boats and I did that pretty solidly for about 2 years and then during a really slow October I decided to take the Captains license test.
Ok wait! Here comes Doug and Clare and Audie. They are sailing in right now. (Roberta blows her conch and Jen blows hers, laughing, yelling, ensue.)
Jen: Please tell them I say hi next time you see them!
Roberta: They’re so beautiful. We are just getting ready for the Thanksgiving Regatta. I am now Vice Commodore of the Coral Bay Yacht Club. Which means that I need to go out and get donations.
Jen: So does that mean you get to wear a cute Vice Commodore hat?
Roberta: Ha ha, I should. I need to talk to Sara O’Neil about that as she is the Commodore. Now Laurie is coming (sailing) in. She just dropped her jib and she’s got her main. It’s a little boat, I think it’s a Choi Lee. So these are the Wednesday night races.
Jen: When I lived in Coral Bay, I loved watching them come in. Do you know that my dear friend Pete Zimmerman started those races with Julian, can’t remember his last name, about 17 years ago. He’s actually my oldest daughter’s Godfather, so they are fondly rooted in my heart.
Roberta: That’s so cool.
Choosing “Captain” Happiness
Jen: Your nickname is Captain Happiness. So what’s your secret to being happy and are you happy every day?
Roberta: Yes! (Laughs) Oh man! You choose it. Even when you have your low moments , you choose it. I have my quiet time that regenerates me and my yoga practice. But the people close to me get to see my grumpy moments too, but really my thing is that you can choose it. It’s my choice to be happy or to be frustrated and sad. In that instant you can choose it. You just dig deep and smile when you’re not feeling it. Because people don’t want to hear it. They want to hear that you are happy or that you’re finding a positive way to work with what life has offered. As we do that guess what happens…it starts to works.
Jen: It does works and also people like to be around you when you’re happy. When you are exuding such good positive vibes it’s very very attractive and what a great name to be called – “Captain Happiness”! If you’re gonna go out for a day on the water, who would you want to go with??
Roberta: You’ll love this. The person who gave me that name told me that she had given many people nicknames but I was the first person she could actually tell.
Secret Spots, and the Perfect Day on the Water
Jen: Is there a secret spot that you really like to take people to?
Roberta: There is a lot. We have a lot of them. One our favorite sayings is “Let us show you the sweetest spots the Virgin Islands has to offer”. And they are secret!
Jen: So does that mean you aren’t going to tell me them in this interview?
Roberta: No, and they’re all over. There are cannons underwater we can show you.
Jen: Like pirate cannons!
Jen: So what’s your idea of the perfect day on the water?
Roberta: I would say when I see people on the bow of my boat totally relaxed chatting amongst each other like they are in their living room. Everybody getting to see something they have never seen before.
“That is one of my goals…to show you something you’ve never seen before.”
To clear the cobwebs and to feel light and relaxed. My biggest thing with my guests is that every boat trip is different. I work the trip with the weather and what my guests want to see, I don’t do the typical boat trip. I help my guests create their idea of a dream day on the water. That’s part of being on the water, creating your dream.
Jen: So what’s the biggest compliment you have ever received.
Roberta: (Laughs) Oh, there’s a lot of them.
Jen: So give me more than one!
Roberta: (more laughing) Uh, when my guests tell me that they’ve had their best day ever. Oh and the other day I had some guests who went out with me one day and then they were swimming at Honeymoon beach, found a Pirate Girl flag and booked another trip to go out with me. So, I guess that was a pretty big compliment.
Jen: Well, think about it. Most visitors have 7 days. 2 days are travel so that leaves 5 days to play. That really is a big compliment to spend 2 days out on the water with the same charter company.
Jen: So have you met anyone famous since you’ve lived here?
Roberta: No, not unless you count the people who live here.
Jen: Yes, there are some pretty famous or infamous characters who live here aren’t there.
Roberta: Yes, like David Wegman, Crab Mon, Sloop Jones. Sloop is probably my most favorite.
Jen: Actually they are on my list of people to interview! I mean it’s endless really. As I was adding this interview segment to the website, I made a list of about 30 people. I looked at this list of fascinating and inspiring people who I’ve had the privilege of knowing and hanging out with over the past 20 years and I was like, I can’t wait to interview these people! It really is the people who make the place. I guess the beautiful scenery doesn’t hurt either. And it started with Captain Happiness! How awesome is that!
Captain Happiness Bar Crawl
Jen: So what’s your favorite cocktail and where can I get one?
Roberta: Mmmmm there are many. Right now it would be my Margaritas. First with Sara at “Indigo Grill” right here in Coral Bay. Then, the Margarita from Carlen at “Joe’s Rum Hut” in Wharfside. And then, to the Casino for a fabulous glass of chardonnay.
Jen: The Casino? In Wharfside?
Roberta: Yes, you get a nice chilled glass of wine for $6 and it’s air conditioned. You can sit in there with your friends and eat peanuts. Plus I’m from Nevada and even though I don’t gamble, I love the whole Casino feel. I also love my Painkillers. I’m a Painkiller girl.
Jen: And who has the best Painkillers?
Roberta: Its still the Soggy Dollar Bar (on Jost Van Dyke) they have the tastiest ones.
Jen: I like the Vanilla-Killa from Soggy Dollar.
Roberta: Yup, they have a mix of a perfect balance of everything in their Painkillers.
Jen: OK, what’s the number one question you get asked by visitors?
Roberta: You know what it is? It’s always, “How’d you get here?” or “Do you live here?” or, wait “Are there sharks?”
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