St Augustine Sailing — Attraction in Florida

St. Augustine Sailing delivered professional, gracious, and sincere sailing lessons that provided this Midwest couple with confidence in our skills and a new outlook for the future! The positive reviews you see are well deserved by a highly trained staff of captains who breath life into the lessons with patience and personal engagement. My wife and I had zero sailing experience but studied hard with the excellent training materials before arriving. The books and various online videos helped with the fast-paced activities once we arrived.

Lauren taught ASA 101 and it was the perfect introduction to sailing basics. Before we knew it, we were zooming across the water in a 22’ sailboat named puffin with my wife at the helm and the wind pressing us forward, smiling like children. Speaking of children, Lauren and the team took a boat full from the school for the blind and deaf out on the water the next day as part of their community outreach and those kids had a wonderful day of sailing.

Nuri and Dale taught ASA 103 and brought such a drive for experience and confidence. We slowly worked our way thru so many different situations and exercises with careful repetition that built muscle memory and confidence. The wind and the waves became tools in the hands of our sails as we helmed through the sea. By the end of two days our confidence grew stronger and the joy of sailing cascaded into pure pleasure with the water burbling behind the transom.

Finally, it was time for Chris to polish our open water and navigation skills with ASA 104. We charted our journey, identified waypoints without GPS and determined fuel, time, and other KPIs on paper charts with ease by the end of the morning. This is another area where good preparation will help. We sailed for hours and gained the practical experience with anchoring, maintenance, and planning needed for coastal cruising and chartering.

You will be new people after stepping away from a week of sailing at St. Augustine Sailing. Confident, alive, and actively planning for your next adventure. The value to us far exceeded any cost and we will always look back to this moment as a turning point in our hearts, as much for the people we worked with as the experience.

The people at St. Augustine Sailing made all the difference between a great time, and a life...

⛵️ St. Augustine Sailing — Where Every Voyage Becomes a Memory ⛵️

If you’re searching for an unforgettable way to experience the magic of St. Augustine, look no further than St. Augustine Sailing. We’ve taken multiple charters with them over the years, and each trip has been nothing short of spectacular — a blend of serenity, adventure, and pure coastal beauty.

Founded in 1985 by Doug Crane and now co-owned by the passionate and visionary duo, Rose Ann Points and Chuck Point, St. Augustine Sailing has stayed true to its mission: combining luxury sailing with hands-on education and unmatched hospitality. With their 40th anniversary in 2025, they’ve not only stood the test of time — they’ve elevated what sailing in Northeast Florida can be.

Whether gliding along the Intracoastal Waterway, catching the breeze on the open Atlantic, or enjoying a calm, romantic sunset sail, the experience is always elevated by the expertise of their US Coast Guard licensed captains. Every crew member we’ve met has been warm, professional, and genuinely enthusiastic about creating memorable moments on the water.

We recently had the joy of attending their 40th Anniversary Celebration, and it was a day to remember! From the fun-filled 75-minute treasure hunt sail (a total delight for the little ones) to the engaging dockside activities like knot tying and pirate photo ops, the entire event was thoughtfully curated. The evening wrapped with mouthwatering BBQ by Chef Wes, live music, and a sunset toast that truly captured the spirit of this amazing company — heartfelt, vibrant, and full of joy.

A special thank you to Chuck, Rose Ann, and the entire crew for their passion, hospitality, and dedication to the local sailing community. You’ve built something truly extraordinary.

📍 Departing from the beautiful Camachee Cove Yacht Harbor, St. Augustine Sailing offers: • Private luxury charters (starting at 2 hours) • Full-day and overnight sailing experiences • Perfect settings for anniversaries, birthdays, engagements, or just a peaceful escape

And don’t miss out on their 40% off anniversary promotion — the perfect excuse to set sail and create your own unforgettable memories.

We’ll definitely be back — again and again. Here’s to smooth seas, sunset sails, and 40 more incredible...

Saint Augustine Sailing made an already special night even more unforgettable. I had planned a Nights of Lights cruise to propose to my girlfriend (now fiancée), and their team went above and beyond to help make everything seamless and stress-free.

From the start, the staff was incredibly helpful and patient. When I called to book, Isla answered all of my (many) questions and helped me arrange champagne, cocktails, and treats for the cruise. She even took the time earlier in the day to show me the 35-foot sailboat I’d booked so I could plan out where and how I wanted to propose. The boat was spotless, well-maintained, and perfect for the evening ahead.

As the day went on, the winds started to pick up, and I got a call from Isla letting me know the conditions might prevent us from sailing. She laid out all of my options and was so reassuring, which made a stressful situation feel manageable. I decided to hope for the best, and she kept in touch with updates.

Just a couple of hours before we were set to leave, I got a text from her asking me to call her. Naturally, I panicked, thinking the worst—but when I called, she had great news. Not only had the winds started to calm, but the team decided to upgrade us to their 40-foot double catamaran at no extra cost to make sure we’d have the best experience possible. I was blown away by their generosity and how much they cared about making the night special.

The crew onboard was amazing. The captain and first mate were welcoming and attentive without being intrusive, striking the perfect balance. It was a chilly evening, and they brought us blankets to stay warm. They even offered to take photos during the proposal, which turned out beautifully and captured the moment perfectly.

This was a night we’ll always remember, thanks to the team at Saint Augustine Sailing. They truly went the extra mile to make everything feel effortless and special. If you’re considering a sailing experience, I can’t recommend...