Originally from Ohio, Devin first came to Oʻahu while traveling and instantly felt at home. More than ten years later, the warm climate, ocean, and outdoor lifestyle continue to keep her here. When she’s not at work, Devin enjoys mountain biking and spending time at the beach. Her favorite part of the job is meeting people from all over the world and helping make their time on the water memorable.
Captain Ken, Founder
Originally from the Pacific Northwest, Ken began his career as a forester before sailing from Seattle to Hawaiʻi in 1985 aboard his 29-foot sloop to start Tradewind Charters. Nearly 40 years later, he remains deeply passionate about life on the ocean and enjoys sharing decades of sea stories and experience with guests while out on the water.
Captain Ashley, Operations Manager
Born and raised on Oʻahu, Ashley grew up on and around the ocean and was drawn to water sports from an early age, whether it was surfing, paddling, or sailing. She got her commercial captain’s license at 19 and has been operating boats ever since. When she’s not on the water or in the office, Ashley enjoys paddling, surfing, and spending time with her pets. Her favorite part of her job is meeting new people and being part of their experience on the ocean. If you’re lucky, you might even spot Captain Pepper (her dog) joining her on board for the day.
Devin, Office Manager
Captain Wes
Born in Lake Tahoe, California, Wes grew up around the water and is a former collegiate swimmer. He moved to Hawaiʻi over a decade ago and quickly found his home on the ocean. With years of experience sailing a wide range of vessels and navigating varied Pacific conditions, Wes is known for his skill, confidence, and smooth boat handling.
Guests often remember him just as much for his connection to the ocean as for his technical expertise. He has a sharp eye for marine wildlife and never misses the chance to point out dolphins, whales, or other ocean life along the way. Wes loves that no two days on the water are ever the same and takes pride in creating memorable, relaxed, and fun experiences for every charter.
When the sails come down, you’ll likely find Wes unwinding with a well-earned Mai Tai and he’s always happy to share his pick for the best one on the island.
Captain Mikey
Born and raised in coastal North Carolina, Mikey developed a strong connection to the ocean from an early age. He has worked internationally as both crew and captain in the yacht delivery industry, completing dozens of ocean crossings on a wide range of vessels. That work brought him to Hawaiʻi in 2019, where he met his wife and began building a family. Mikey enjoys sharing his love of life on the water with his son, Sonny, and carrying on a family tradition rooted in the sea.