Captain RJ
Originally from Alaska, Captain RJ began sailing many years ago in Puget Sound, surrounded by the mountains and skyline of Seattle. Eventually, the call of warmer wind and water inspired him to sell his businesses, downsize his life, and move to St. Thomas to become a sailboat captain.

Soon after arriving in the USVI, RJ became co-captain of Rumbaba, a lively 39-foot Hunter monohull day charter boat. With beautiful scenery, snorkeling with turtles, grilled lunches, fresh cocktails, and plenty of island charm, each outing became something special for guests, helping Rumbaba earn recognition as one of the top activities on St. Thomas.

RJ’s sailing journey later led him back to Puget Sound, where he joined slick racing sailboats and began teaching at Seattle Sailing Club after earning the proper certifications through the U.S. Coast Guard and American Sailing Association. Teaching quickly became a calling, and it was during this chapter that he met Jenna, who shared his curiosity and excitement for a Caribbean sailing life.

About six months after an invitation from his original sailing instructor, RJ moved to Grenada to teach term charter sailing. Sight unseen, he immediately fell in love with Grenada and the Grenadines, enjoying the warmth of the people, the beauty of the islands, and the joy of helping students learn to captain boats of their own.

Over the years, RJ and Jenna have sailed more than 20,000 nautical miles together, helped graduate over 300 ASA students, earned two Outstanding ASA Instructor of the Year awards, and created hundreds of new friendships along the way. RJ also enjoys scuba diving, kiteboarding, hiking, traveling, and, when stateside, lacing up his skates whenever he can find an ice rink.

Chef Jenna
Chef/First Mate Jenna grew up on Newman Lake, Washington, a beautiful lakeside community outside of Spokane. Her love for boating began at a young age, sitting on her dad’s lap while racing the speedboat from shore to shore. Later, her move to Seattle gave her even more access to life on the water, where she enjoyed sailing Puget Sound, boat camping around the islands and bays, and crewing for the beloved Duck Dodge races on South Lake Union.

Jenna first met RJ while he was teaching sailing in Seattle. At the time, she was a lighthearted beer can racing sailor, fascinated by his plans to build a Caribbean sailing life. RJ moved to Grenada, and Jenna soon began joining the adventure, first as an ASA student herself and then for more sailing, exploring, and time on the water.

As their shared passion for sailing grew, so did their life together. What began as visits and adventures became a full partnership both personally and professionally. Teaching became a calling for them both, and they began offering private couples’ cruising instruction, helping others with similar dreams learn how to make a sailing life a reality.

Together, Jenna and RJ have sailed more than 20,000 nautical miles, helped graduate over 300 ASA students, earned two Outstanding ASA Instructor of the Year awards, and built a life full of new friends, adventure, and unforgettable memories.

When she is not sailing, Jenna enjoys scuba diving, kiteboarding, hiking, traveling, and spending time with family and friends. Stateside, she gets especially excited when she can strap on crampons and climb toward the tallest mountain.