ABOUT US
We are a small Hawaiian ohana-owned and operated business.
A family of five, Kaleo, Leila, and there 3 sons, Kaeo, Hau’oli & Makana, share their love for the ocean to visitors and locals alike through their family-style charter boat company, Ohana Ocean Connections on the Kona Coast of the Big Island of Hawaii, founded in 2025. Ohana Ocean Connections is the sister company of Ohana Surf Lessons, founded in 2020.
Charter Captain / Hawaiian Surf Instructor:
Lifetime Native Hawaiian surfer Kaleo Waiwaiole was born and raised in Hawaii and grew up in Kailua Kona. Having been raised around the ocean his entire life, Kaleo started surfing at the age of 5 and has worked in the surf school and commercial boating industry since age 13, where he acquired his skills to become a snorkel tour boat captain at age 21.
As an overall waterman who has always enjoyed surfing, diving, paddling an outrigger canoe and many other ocean activities. It was always a dream and a goal to own and operate his own surf school out of his hometown of Kailua Kona. By using his acquired skills in the water after years of teaching lessons and his knowledge of the surf school industry, Kaleo made his dream a reality by founding "Ohana Surf Lessons" in 2020 at age 25 and has now taken out thousands of people surfing since his youth.
Over the years, Ohana Surf Lessons has grown into a successful, well-known and recognizable surf school on the Big Island, known for its family surf lessons, offered at several locations in the Kona area, local style surf instructors and a high reputation for safety and delivering quality.
As someone who refuses to stop chasing his dreams and now with a family of 5, Kaleo and his Ohana have expanded their operations, forming a partnering, sister company offering snorkel charter tours out of Honokohau Harbor on the Kona Coast.
The same harbor in which Kaleo grew up, working, remembering, enjoying, and visiting often as a young child.
The kid who would ride his skateboard to the harbor, down the steep hill from Kealakehe High School, up above, would clock in wheels blazing hot from asphalt, for his after-school job at the local surf and dive shop for the evening Manta Ray snorkel tours five nights a week. He would eventually invest in his own boat, forming his own charter tour company
Ohana Ocean Connections in 2025 at age 29.
Kaleo continues to enjoy sharing his love for the ocean and marine life through a variety of different excursions and activities offered by his family-run, charter company and surf school, over 15 years later, after his first job at the small mom and pop surf and dive shop where it all began.