Your Crew
Leading the company, Captain Jack is a certified sailing instructor for the American Sailing Association, and was named the 2022 ASA Instructor of the Year. With around 100,000 nautical miles under his belt, 5 ocean crossings, international racing and his RYA Yachtmaster, he brings extensive experience from working as a captain and instructor around the world.
Jack's sailing career began when he crossed the Atlantic aboard the original La Vagabonde monohull with his cousin Riley and Elayna, who had just launched the now ultra-popular YouTube channel 'Sailing La Vagabonde'. Jack pursued professional certifications, completing his Yachtmaster qualifications in England and working as a skipper for a major flotilla company before transitioning to instruction, where he found his calling.
After gaining experience in the charter industry across multiple continents, Jack founded Vagabonde Adventures. His teaching philosophy centers on maximizing hands-on experience for his students and guests. Jack is passionate about coaching sailors of all levels and consistently works to extract the best performance from both crew and vessel.
Whether sailing across Atlantic passage or leading snorkeling excursions, Jack combines technical expertise with an enthusiasm for sharing his knowledge. His background, from first getting on the helm in his 20s to now becoming an award-winning sailing instructor, gives him a unique perspective on helping others discover their own sailing journey.
Along with Jack we have an amazing group of professional captains you may be lucky enough to sail with.
Jansen Charter
We had the most incredible week sailing with Vagabonde Adventures! From start to finish, the experience was smooth, educational, fun, and so welcoming. Jack and Daryl made everything feel easy and relaxed, while also making sure we were learning and fully immersed in the experience.
Jack was amazing with our whole family—patient, kind, and a fantastic teacher. He not only made sailing fun, but also made sure to share as much knowledge as we could absorb throughout the week. He encouraged the kids to snorkel, dive, and enjoy every part of the adventure—not just the sailing—which made the trip even more memorable. He met everyone at their own level, included the kids in everything, and helped build their confidence with such ease.
Daryl not only made the most delicious meals all week, but she also went out of her way to accommodate my food intolerances with such kindness and care. She always found great options that worked for everyone, and even came up with fun cooking activities to keep the kids entertained during the longer stretches on the water.
By the end of the week, our kids were asking if we could move to the ocean and live on a boat—and honestly, we understood the feeling! They made the days fly by, and we made memories we’ll hold onto forever.
We would 100% recommend Vagabonde Adventures to anyone looking to learn to sail, connect as a family, and enjoy an unforgettable experience on the water. Truly a 10/10 trip!
PN Charter
Spent a week with Jack and Eta on a charter for a week of fun sailing in Greece and getting ASA certified at the same time. To say it was fantastic fails to capture all the hundreds of small moments that made the week so great. From chilled out evenings hanging out on deck, walking in small villages onshore, learning so much each day, and being in the company of such wonderful people.