October 4, 2023
ATS NE May 2023
Rose Ann and Chuck Points bought St. Augustine Sailing in 2018.

Photo: St. Augustine Sailing

ATS NE May 2023
St. Augustine Sailing offers private luxury charters and sailing lessons.

Photo: St. Augustine Sailing

ATS NE May 2023
Fort Mose Historic State Park in St. Augustine, which was the site of the first legally sanctioned free African settlement in this country established in 1738, will undergo reconstruction to transform its appearance into what Fort Mose looked like in the 1730s.

Photo: Florida State Parks Foundation

Northeast Florida Roundup

Smooth Sailing

Vanessa Caceres | 5/31/2023


Smooth Sailing

St. Augustine Sailing, which offers private luxury 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 Points have had a longtime connection to sailing. Rose Ann began spending time on boats in Washington state in her mid-20s and then purchased a double-masted sailboat and lived on it with her children for 13 years. She later met Chuck when he was working with St. Augustine Sailing.

St. Augustine Sailing was founded in 1985, but the couple bought it five years ago. Three adult children have jobs that include booking reservations, serving as a photographer/videographer and managing a fleet of sailing yachts. In addition, there are some spouses involved in the business and grandchildren who come to visit regularly.

In addition to five full-time employees, the company also has 21 contract workers.

“We have had a 25% growth since we purchased the business,” Rose Ann says, “Since COVID — depending on the quarters — we have dropped 16% to 37% from the previous years.” However, she says, it’s still greater than their pre-purchase revenue. “We are hoping this year we will be back to pre-COVID numbers.”


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  • Mayo Clinic in Jacksonville is adding a 210-acre north campus, growing its footprint to 602 acres. The Davis family, which founded Winn-Dixie Stores, conveyed the land to Mayo Clinic late last year. Plans for the additional area include technology hubs and experimental learning spaces.
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