Rose Ann Points had never so much as stepped a Sperry onto a sailboat when she and her then husband made the bold decision in 1996 to uproot their comfortable family life in Oregon and travel the Caribbean aboard their own vessel. But as wild as the idea may seem, Points needed little convincing when her husband spontaneously suggested the adventure: She had grown up in a small town in Oregon with a dream to see the world, and aspired to a career as a flight attendant.

“When I started sailing, I was 30 years old, and I didn’t know how to do anything,” she said. “I didn’t have any resources or anything. Now that I’m in the position I’m in, I really want to help other women who either want to be a skipper themselves or be a reliable first mate, or an individual that, if they’re asked to do something, they’re not intimidated by whatever that task may be.” 

Kim Walther is a sailing instructor at St Augustine Sailing located in Northeast Florida... She has a self proclaimed obsession with the outdoors and has sailed the east coast from Maine to the Caribbean.

St Augustine has a long and distinguished sailing tradition going all the way back to the 16th century. So it's no surprise that some of today's most dedicated sailing enthusiast have decided to drop anchor here.

St Augustine Sailing, which offers private luxury sailing charters and sailing lessons, has not just one, two, or three family members involved in the business. There are seven of them working together. Co-owners/spouses Rose Ann and Chuck have had a longtime connection to sailing.