One of Us

Rose Ann Points


With husband Chuck Points at her side, Rose Ann Points manages St. Augustine Sailing, the local SailTime franchise and the new-and-used boat sales brokerage, Yacht Sales by Rose Ann. She began her boating life cruising the Columbia River in Oregon with her family. In 1996, she moved to Florida and lived aboard a ketch with her children for 13 years.

Tell me about your background growing up on the water and living aboard a ketch for several years.

I grew up in the country, a small town in Oregon. We had a river within a mile or so and as a family we would go and relax on the bank. Although my mother gave me swimming lessons, I really never learned to swim, but I loved the water anyway. I got married and moved to Washington state at 26. This is really the beginning of my boating life.

We had a cabin cruiser that we would go on during the weekends and vacation on during the summer. After selling everything we owned, at 30, my family traveled from Washington state to Florida in search of our new home, which happened to be a 41-foot Morgan OutIsland Ketch purchased in West Palm Beach.

Since none of us knew how to sail, with the exception of reading how it was done, our family moved aboard. We took short trips around the Keys, Everglades and Tortugas before we began our grand adventure across the Gulf Stream. We had to get out of Dodge, you might say, before 90 days of purchasing our sailing vessel so this made our learning and getting used to living on the vessel really urgent.

I think it took me at least two months to become accustomed to living aboard, my boys — I think maybe one day.

Life aboard Tranquility was fun but not without challenges, too. We did not have refrigeration, so it took some time to learn how to live without it. We lived off the ocean; my boys fished every day. In the whole 13 years we lived aboard I never had to clean a fish; our rule was they caught whatever they wanted to eat, bring it back to the boat ready to be cooked and my daughter and I would cook it.

We ate a lot of conch, lobster and grouper (since that was my favorite fish).

We generally traveled off the beaten path. We loved going to locations that were not touristy so we could experience real life. By doing this we often made lifelong friends, learned how to cook like the locals and enjoyed a very simple life. Our days often consisted of breakfast together, school for the kids (9 a.m. to noon), lunch, siesta (most of the time it was just hanging out in the cockpit talking or playing games) until around 2 pm. Then swimming and exploring the areas around us. Then the boys would get something for dinner, and we would go back to the boat.

After dinner we would sit in the cockpit or lay on deck and play a game, or talk about the day, talk about creation and how through creation we could know and learn about our Creator. We regularly read and studied the Bible together.

Sometimes, we would stay at one location for just a day and others maybe a few months. It all depended on how much we enjoyed the area. One of our favorite places to anchor was a cove that had three small deserted islands around it. It was comfortable, with a nice small beach that was protected, beautiful clear warm water, great snorkeling, lots of fish, lobster and conch. Only a few days’ sail to a reasonably sized grocery store, which we only went to every few months.

Tell me about the charters offered by St. Augustine Sailing. Where do they travel and what kinds of experiences do they offer?

St. Augustine Sailing offers a variety of sailing experiences:

  • Day sails
  • Sunset sails
  • Culinary sails: brunch, lunch, dinner, charcuteries, desserts 
  • Wine tasting sails: Sip & Sail experience, choice of one or two hours
  • Special occasions: proposals, elopements and wedding experiences
  • Educational: dolphins, turtles, birds, manatees and just nature in general
  • Land and sea packages
  • Vacation sails: multiple days. We stay in St. Augustine and sail in the ocean during the day, travel to Cumberland for a three- or four-day trip, travel to Daytona for a three- or four-day trip. On longer trips, you could go to Miami or the Keys.

You also offer sailing lessons and membership in SailTime. Can you tell me a little about that?

  • Instruction from beginner to advanced using American Sailing curriculum to receive a certification. And then for those who want to dip their toes in but are not quite ready to take the leap, we offer a two-hour intro to sailing. 
  • Crew membership: Two Sundays per month, our captain selects one of his or her favorite sailing vessels from our best-in-class luxury sailing fleet and the crew members get to join them on board and help sail the beautiful waterways of St. Augustine. Our goals are to help you build and/or improve your sailing skills and build a solid sailing community, all while having fun on the water. With our crew membership, sailors can join our weekly crew sails every Sunday with a choice of 10 a.m. to 1 p.m. or 1 p.m. to 4 p.m.  
  • Augustine Sailing’s WOW! Program (aka Women on the Water) is designed by women for women. The purpose of the program is to make sailing an attainable goal for all women. The program will run every weekend throughout the year, focusing on different topics each month, modified to fit every level of experience. The program will cover “all things sailing.”
  • SailTime offers guaranteed access to your boat every month. You can make reservations online up to one year in advance. With SailTime PLUS, members can rent boats at other SailTime locations at a mere fraction of the cost of regular bareboat chartering.

I know you also offer yacht sales. Are there certain types or brands of yachts you handle? Also, how is delivery arranged?

How the vessel is delivered depends on the manufacturer of the boat. The vessels generally arrive on a cargo ship and, depending on the size of the vessel, some are wet delivery (from cargo ship straight to the water) or transported (loaded to a transport truck) to a yard to be commissioned.

After they are commissioned (for a sailboat that means building and installing the mast, standing and running rigging, putting the sails on, canvas, and installing any other options the customer chooses), if the customer is putting the vessel into our charter fleet, then the vessel is delivered to our location in St. Augustine. Otherwise, delivery or handover is done at the location where the vessel is commissioned. The vessel is splashed, and the buyer and I go out for a shake down sail and go over all the equipment and options ensuring the buyer knowns how everything works. Depending on the size will determine the length of time required to complete the handover. 

As a franchise base for SailTime, we offer Jeanneau, Beneteau and Lagoon brands. We also partner with a local Jeanneau dealer for power boats this area. We also partner with a local Catalina dealer. 

If someone reads this article and is interested in either a charter or lessons or in purchasing a yacht, how would they arrange it?

Call 904-829-0648, email or go to @StAugustineSailing (Facebook, Instagram and YouTube.

What do you like best about living here on the First Coast?

For me, living on the First Coast is the best of both worlds. The ability to live a simple life in a beautiful surrounding. The area isn’t so developed that you can’t see the stars at night or enjoy creation because it is paved over. Everywhere you look you see plants, sea creatures, birds, insects and land mammals. Each of these things brings joy and happiness when looked at and examined and meditated on.