Our Story

About Us

St. Augustine Sailing Enterprises has been described as a luxury adventure experience that accommodates different budgets. Its private charters are a popular choice for family outings and special occasions. Specialty themed charters are offered on a daily, weekly, and monthly basis, pairing world class culinary with the sights of the sea and city.

St. Augustine Sailing also offers sailing lessons and membership in SailTime, a sailing club that allows members to rent a boat anywhere there is a franchise. Rose Ann Points said what she likes best about her business is helping people to fulfill a dream they’ve had for a long time.

“For me, it’s all about the experiences,” she said. “It’s about the adventure. So, getting to know (the customers), finding out what it is that they want and then helping them find a path to fulfill that dream and make it a reality for them.” For Chuck Points, it’s all about getting out on the water. “You’re out sailing quite a bit,” he said. “It’s quite enjoyable, and the people are great.”

Aside from the excursions and other services offered by St. Augustine Sailing, All Points Yacht Sales handles the sales of these watercraft.

What Makes Us Unique


We have the newest and cleanest yachts on the water. Our Yachts are only one to three years old.


We are fanatical about customer service and are here to exceed your expectations


LUXURY at an affordable price. We truly have the most premium on-water adventures available in St Augustine.


We are proud to customize all of our sailing experiences to ensure that every guest “sails” away with magical memories

Meet the Owners

It’s no surprise that some of today’s sailing enthusiasts have decided to drop anchor in St. Augustine’s waters, as the city has been part of a sailing tradition dating back to the 16th century. Among those who have anchored here are Rose Ann and Chuck Points, owners of St. Augustine Sailing and All Points Yacht Sales.

Rose Ann Points began her boating life cruising Oregon’s Columbia River with her family. In 1996, she moved to Florida and lived aboard a ketch with her children for 13 years. Later, she came to St. Augustine to get certification and met the man who would become her husband.

Chuck Points got his start sailing when he was 15. He lived near a yacht club, the members of which were always looking for crews. Signing on, he began an adventure that would chart his course through life. He went on to sail in Asia, Europe and other places. He came to St. Augustine in 2004 to rent a boat and, when it was discovered that he had a captain’s license, was offered a job. And that’s where he was when the future Rose Ann Points walked through the door. The couple married in 2012 and, in 2017, they purchased St. Augustine Sailing.

Rose Ann began her boating life in the Northwest cruising on the Columbia River aboard a 27-foot powerboat during weekends and vacations on the water with her family. In 1996, she moved to Florida to live aboard a Morgan Out-Island Ketch with her three children for 13 years. She has sailed along the East coast from Maryland to the Tortugas and up the west side of Florida, spent about nine months traveling throughout the Bahamas, and time in the Caribbean such as Puerto Rico’s Spanish Virgin Island and British Virgin Island as well as other Caribbean locations. She holds a 50 GT United States Coast Guard masters license with Aux Sail Endorsement. She manages St. Augustine Sailing and the company’s various member clubs, the local SailTime franchise, and the new and used boat sales brokerage  All Points Yacht Sales. Rose Ann founded a variety of team building programs and established a myriad of sailing activities. She established Women on the Water (WOW) to enhance the lives of women through education, practical application and access to sailing vessels, and to develop skills to sail with confidence.

Chuck, a lifetime sailor, has traveled and sailed all over the world.  He has had the opportunity to experience sailing areas such as Australia, Asia, Europe, Portugal and a variety of different sailing areas / environments from Lake Superior to South China Sea.  Sailing has been his lifelong passion and even today he enjoys sharing this exciting experience with all that visit us here at St Augustine Sailing.

He oversees all sailing operations and is the primary delivery captain. In addition to holding a USCG Masters 100 GT Captain License with an Aux Sailing Endorsement, he is a certified American Sailing Instructor.  He has been awarded the ASA Outstanding Instructor of the year.  Under the direction of Chuck, numerous instructors here at St Augustine Sailing have also been award the same honor of being the Instructor of the year.

His passion  for being on the water extends to being under the water as well. He was a dive instructor up until a few years ago.  He loves all thing nature and enjoys talking about all his beautiful experiences around the world.  His lifelong goal is to circumnavigate the world… the last thing on his budget list you might say.

As a Vietnam War Veteran and serving in the U.S. Marines, St Augustine Sailing offers military discounts for all of our sailing courses and even an annual scholarship for a female veteran to participate in our “Women On the Water” (WOW!) program.