C A P T A I N | RJ Portman
C H E F | Jenna Taylor

This fun sailing duo has been on the Caribbean blue together for nearly 5 years! As adventurers, delivery crew, private charter crew and as sailing instructors; RJ and Jenna have always found a way to sail together.

Captain RJ, originally from Alaska, began sailing many years ago in the Puget Sound, surrounded by mountains and the beautiful city of Seattle. Longing for warmer wind and water (as many of us do), RJ decided to sell his businesses, officially downsize his life and move to St. Thomas to become a sailboat captain. And that is exactly what he did. Not long after moving to the USVI, RJ found himself the cocaptain of a fun little day charter boat named, Rumbaba. Though she was a simple little 39ft Hunter monohull; Rumbaba was a blast to take guests out on. Incredible scenery, snorkeling with turtles, delicious grilled lunch entrees and all the fresh cocktails you could handle made each outing something special for every guest. Making the top 10 of all activities to do on St. Thomas and Trip Advisor verified that!

First Mate Jenna grew up on Newman Lake, Washington; a beautiful little lakeside community outside of Spokane. Her love for boating began from a very young age; sitting on her Dad’s lap and racing the speed boat from shore to shore. Jenna’s eventual move to Seattle only gave her more access to playing on sailboats on the Puget Sound. Loving the city, but needing escape, boat camping, or as Jenna would say, “Bamping”, around the many islands and bays of the sound became a frequent weekend event. She
could also always be found as steady and faithful crew for the infamous Duck Dodge races of South Lake Union!

The wind and the sea continued to call on RJ too, and he found himself as crew on some pretty slick racing sailboats. Again however, the warmer wind and waters of the Caribbean continued to call; this time, literally…

RJ’s original sailing instructor, from many years earlier in Seattle, was on the other end of that phone call. He had established a sailing school in Grenada and, through social media, had seen that RJ was back in the Puget Sound sailing.

“Have you ever thought about teaching sailing?” he said through the phone. “I think you’d be great at it.” He added.

RJ laughed at first, “Man, I’m still out here learning to sail!”

His response was all RJ needed to hear: “RJ, there is no better way to learn than to teach.”
And with that, the next chapter of sailing began. RJ diligently acquired all the proper certifications through the US Coast Guard and the American Sailing Association and began to teach sailing at Seattle Sailing Club. What a blast! RJ absolutely found a calling. This is also when he met his beautiful wife, Jenna. She was a lighthearted beer can racing sailor when they met and she was fascinated with his plans to live a Caribbean sailing life. He was going and he hoped she would visit, often.

After about 6 months from that first important phone call, RJ moved himself to Grenada. Sight unseen prior to arrival, he immediately fell in love with Grenada and The Grenadines. How can you not? They are the friendliest people in the Caribbean; hands down. And beauty was everywhere! What a place. “Work” was teaching term charter sailing and exploring all the amazing little spots along the way. Oh
what fun this job is! Teaching people who are so excited and switched on to learn how to captain a boat for themselves. Many students planned to charter boats with their family and friends, some just wanted to see what it was all about by testing their will (and stomachs) and still others came to learn how to sail off into retirement, literally.

Jenna continued to join the Grenada adventure. At first as an ASA student herself. She kept coming back to join RJ on more adventures and for more sailing. Their combined passion for sailing has only been surpassed by their love for each other. The more they sailed, the more obvious it became that this was to be their wonderful and adventure filled life together. Teaching became a calling for them both and they began to charter private couple’s cruising instruction. Does it get any better than that?! Working with your love and teaching other couples with similar dreams to yours how to make it into a reality! It has been truly amazing. Just ask them and you will get the fully animated version… they don’t tell short stories… Haha, what fun would that be?!

5 years later; RJ married the beautiful Jenna. They’ve sailed over 20,000 nautical miles together. Over 300 ASA students graduated. 2 Outstanding ASA Instructor of the Year awards. 100’s of new friends and lifetimes of memories. Life has been good to say the least.

It’s not always sailing for these two… whenever possible, Jenna and RJ enjoy scuba diving, kiteboarding, hiking and traveling together. Stateside, RJ laces up the skates whenever he can smell an ice rink and Jenna gets all giddy when she can strap on the crampons and climb to the tallest mountain. Family and friends are always in the mix everywhere they go.

So now it is time to make some more new friends and show you all the beauty that the Virgin Islands have to offer.