St Augustine Sailing

Where to begin?! So many great things to say about this experience, the company and the captain! Truly from beginning to end I was impressed with the warmth and professionalism of the team at St. Augustine Sailing. I visit St. Augustine once a year for a spa + boating getaway and when I came across SAS I was thrilled to find they offered a sailing option with brunch in addition to so many other wonderful options. I called to ask a couple questions and the customer service etiquette and the friendly smiles of the staff, Lauren & Dirk, on to the day of my outing were excellent. Owner, Roseanne, was also delightfully to speak with and has done an amazing job with leading her team and attention to details. I had Kevin as my Captain and when I say he took the day trip to the next level of expertise, comfort and enjoyment for my time out on the water - he did not disappoint. He was kind, friendly, engaging and super knowledgeable. He was informative of the area as we sailed and gave good local recommendations for the rest of my stay. Hands down SAS is the areas BEST yacht and sail boating company offering a more private and exclusive experience away from the hustle and bustle of the overcrowded tourist boats. The added luxury of their gorgeous fleet is well worth the cost which was also very affordable for the over the top experience they offer. I love to travel and am always looking for a personalized experience and this was it! I’ll be back and I’m bringing friends. I’ve found my go to when visiting St, Augustine!

My husband booked this excursion for my 56th birthday and Capt. Daniel did not disappoint! This was such an awesome adventure. Captain Daniel pulled out all the stops to make sure we enjoyed our sailing time. So happy we tried your sailing excursion! Definitely a memory made

It was a 50th party for my daughter. St. Augustine sailing was awesome, they helped us plan and execute my surprise. Dan was our captain and provided excellent service and lots of information on things we never saw from the water side. I am sure you will see us again!!! So much fun, and a gorgeous sunset!! I highly recommend this sailing service, I can't say enough about our experience!! Thank you, thank you, thank you!!!😃😃😃🤗 So memorable!!

⛵️ 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 years! 🌊⚓️🎉

First time booking a private charter session and Dan our captain was so friendly and attentive. Some friends and I were lucky to catch the gorgeous sunset skies along the route and saw some dolphins and they provide alcoholic beverages at the office directly so it’s convenient. Ride was smooth and I will definitely book directly with them next time I visit!

My wife and I did a 4 our intro to sailing course and it was fantastic. We can't thank the staff at St. Augustine Sailing enough - especially our informative, professional and experienced captain, Lauren.

Fantastic way to spend two hours. The entire crew is welcoming, friendly and kind. We were fortunate enough to be the only two guests on this outing so we enjoyed especially attentive service, but we’re also sure a larger group would also get the same. Each of the appetizer plates and the wines paired with them were exquisite, delicious, and explained to us in detail, and our host/chef graciously also served us small steaks that weren’t on the planned menu. The scenery throughout the smooth sail is beautiful and the final sunset is gorgeous. Highly recommend !

We had an awesome sail with Daniel. This was our second time sailing with St. Augustine and we will absolutely come back again. Daniel upgraded our boat and also brought us a charcuterie board. The weather and views were absolutely amazing. We highly recommend sailing with St Augustine.