From the moment we stepped aboard, Rose Ann and her crew made us feel like welcomed guests rather than customers. The hospitality was exceptional, the chef prepared a delicious tasting menu, and every detail was thoughtfully planned. The combination of outstanding food, attentive service, and a beautiful sunset sail created an unforgettable evening. Relaxing under sail with incredible views of the water, great conversation, and amazing cuisine made this one of the highlights of our trip. Our highest recommendation. We would do it again in a heartbeat. Thank you, Rose Ann and the entire St. Augustine Sailing team, for an evening we'll remember for a long time. read more

A Truly Unforgettable St. Augustine Sunset Dinner Cruise! We were thrilled to experience St. Augustine Sailing's incredible 3-hour Sunset Dinner Cruise! The night was magical, with gorgeous views of the bay, playful dolphins, and the absolute highlight--a five-course dinner by the talented @ChefWesleyNogueira from @khloeskitchen. Each course was a delight, from the artisanal charcuterie platter to spiced chicken meatballs with cranberry chutney, squid in tomato sauce, a perfectly cooked steak with mushrooms and ravioli, and a chocolate cake topped with Ferrero Rocher. Every bite was exquisite, and the sunset-lit waters of St. Augustine added a perfect touch of serenity. If you're celebrating a special occasion or just want an extraordinary evening, I highly recommend this cruise! A blend of fine dining, scenic beauty, and peaceful moments on the water--this experience is truly a must-do. Book now: 904-829-0648 St. Augustine Sailing, Camachee Cove Yacht Harbor, St. Augustine, FL read more

See all

I enrolled in ASA101 and ASA103 to learn how to sail, starting with very little sailing knowledge. The experience far exceeded my expectations. My instructor, Nuri, was not only highly knowledgeable but also made the learning process enjoyable. He explained the techniques in a clear and accessible way, even for a complete beginner like me. Nuri's expertise and teaching style made everything feel within reach, and I quickly gained the confidence I needed to learn. Feeling inspired, I joined Women on the Water to continue my sailing journey. After years of waiting to learn how to sail, I'm excited to be on this path. Though I still have a lot to learn, I'm thrilled that St. Augustine Sailing offers so many courses to help me improve and eventually become a skilled sailor. I highly recommend this sailing class to anyone, whether you're just starting or looking to sharpen your skills. I can't wait to get back out on the water! read more

St Augustine Sailing - The sailing vessel we practiced on for ASA103!!!! - Boat Charters Near Me - St. Augustine, Florida

Great brunch trip with Captain Kevin. Awesome sailboat, incredible overall. It was our first time on a sailboat and we had a blast. Thanks! read more

I trained with them for 7 days straight. I was able to get my ASA 103, 104 and 114. Captain Dale was my instructor for 103 (Coastal cruising) and 104 (Bareboat cruising). He was thorough, professional and patient. Captain Nuri was my instructor for the 114 (Catamaran qualification). He too was thorough and professional as well as a great shipmate. The catamaran course was far less technical than the classes Captain Dale taught and we were able to really enjoy a beautiful day on the water. The boats were almost brand new and well maintained. I have been to other sailing schools and clubs and this one was the most well run and professional I have ever seen. We had to contend with some bad weather during the week but on the nasty days we worked in the classroom and sailed when the weather was good. These pics are from the last day on the cat. As you can tell I was pretty stressed. All kidding aside I can't give them a high enough rating. They are a top notch school. read more

St Augustine Sailing - Acting like I know what I am doing. - Boat Charters Near Me - St. Augustine, Florida

See all

Today was my very first time sailing in beautiful Saint Augustine. I was very blessed to have five family members join me on a Brunch Cruise provided by St. Augustine Sailing. The weather was absolutely perfect and water mostly calm. The two hour boat operated by the awesome Captain Chris was a very relaxing and wonderful experience. Captain Chris educated us on the area including the types of animals we may see and other types of boats on the water. The entire staff that helped make this charter experience possible were courteous and professional. The beverages were refreshing and the food was fresh and delicious. Thanks so much to St. Augustine Sailing for making this pre Mothers Day '23 Family outing a safe, fun and memorable one. This amazing experience was in honor of my beautiful mother Betty who passed away in 2000 of cancer and sadly didn't have the opportunity to go on a boat trip here as she had wanted. My family and I look forward to coming back soon and highly recommend St Augustine Sailing! read more

See all

THE best place to learn to sail, upgrade your sailing skills, charter or buy a boat. This family owned business is terrific. I have studied & sailed with them (& several of their Captains) for several years now. They also offer a Saturday Women on the Water class covering various topics and several options to join crew. Rose Ann Points, owner is featured in a recent Garden & Gun article of her crazy start in the sailing world. Delightful read! read more

St Augustine Sailing - Boat Charters Near Me - St. Augustine, Florida

Good business, the sailing 114 class was great. The catamaran we were on handled well as the instructor gently guided us through docking, anchoring, mooring balls, collecting a man over board. Imbued confidence read more

Charted about a 32 foot monohull sailboat for 4 hours so we could leave the bay Area and go out in the ocean. There were 4 of us and we had a really good time. The weather was perfect and our captain was Ken. He showed us a little about sailing, had us help with the sails some and we even got to steer for awhile, loved that part. There were some shrimping boats in the area that he got close to so that we could see the dolphins following the boat. It was a really good time and I would recommend St Augustine Sailing and Captain Ken anytime. We will try to do another sailing trip with the kids next time we are there. Note that they also do certification training/lessons on sailing. Could be really nice to try that too. The lessons are 1 day to 5 days long depending on what certifications you want. read more

St Augustine Sailing - Boat Charters Near Me - St. Augustine, Florida

See all

I'll start out by saying that my son and I had initially planned to take a boat tour out of the marina in downtown St. Augustine, but we missed the boarding time - and I'm glad we did. After doing some quick research on other options, I came across all the great reviews for St. Augustine Sailing, and as I'm a big fan of sailing as opposed to motoring I thought we would give it a try. Their marina is just a few minutes away, and the staff there are all WONDERFULY hospitable (like they invited us to have some lunch with them since they had just finished preparing wings). We booked an afternoon shared sailing time, and as it was only my son and I, we had the boat to ourselves. It ended up being a perfect day on the water. Captain Dale is truly passionate about sailing and teaching and is highly knowledgeable about the area and its history. The weather was perfect, and it made for a truly unique adventure. My son is 4.5 years old, and when I ask him "What would you like to do this weekend...? Go to the Zoo, the Science Center, or Chuck E. Cheese?" He thinks about it and then says, "I'd really love to go sailing again!" I'm writing this review as I'm currently booking another outing for us to go and see the "Night of Lights" during an evening cruise. read more

We did the ASA 101-104, We worked hard and laughed hard, both instructors were very thorough and had lots of patience. Ran through the drills to the point we feel confident about taking a sailboat out and safely bringing it back with all hands still on board. read more

St Augustine Sailing - Wing on wing - Boat Charters Near Me - St. Augustine, Florida

See all

We had an awesome time on 007, a luxurious Lagoon 38 catamaran! Captain Kim was awesome, went off shore and cruised by the Bridge of Lyons and downtown St. Augustine is absolutely beautiful from the bay. It was the perfect adventure for friends that came in from out of town. read more

See all

Sip n' sail was amazing. Captain was great! Got to enjoy a plane doing stunts while also enjoying the sunset.

Very good sailing school. Captain Chris was an excellent coach for our ASA 114 class! Well done and I can highly recommend St. Augustin Sailing! Great facilities, boats, marina, training and instructors! read more

We enjoyed a beautiful, peaceful and wonderful two hour sail with Captain Jeff. Great 34 foot sloop, clean, neat, safe with interesting sights and waters all about. Very much worth the money and time. Interesting note, when we returned to our Casa Monica hotel, we stopped by the hotel services desk and told the young man we wanted to discuss sailing. Without hesitation or allowing us to speak, he said there were not companies in St Aug providing small sailing charters. When we mentioned St. Augustine Sailing, he simply said he'd never heard of it, and that was the end of the conversation. read more

A must do when in Saint Augustine! The best way to see the city! My wife and I have done this several times with guests and everyone always has a great time! The staff at St. Augustine Sail are always friendly and patient. The boats are beautiful and very well taken care of. Everyone involved has a true passion for sailing and they all enjoy sharing the experience of being on the water with others. An incredibly well run organization! I highly recommend making time for an excursion with St. Augustine Sail when visiting the area. read more

My husband and I took a 2-hour learn the ropes introductory cruise with Captain Chris. What a beautiful sailboat we sailed on. It was a perfect day! Our Captain was excellent and very knowledgeable in all aspects of sailing..starting with safety first! We both learned a lot from him and are seriously considering taking more classes. Thank you for a great sailing experience! I highly recommend St Augustine Sailing! read more

Awesome captain, great experience. We did "learn the ropes" and it was a good introduction to sailing and was well taught. Captain was obviously very experienced and had plenty of knowledge to share. It was a lot of fun! Highly recommended. read more

I purchased a Localflavor for up to 6 people on a captained charter with St. Augustine Sailing. What a deal and great experience! The actual spot was a little hard to find, so give yourself some time. (Go left when you pull in and go most of the way down). While you wait there is a nice lounge with seating, TVs, games, etc. and the restrooms have showers and laundry available. We booked a 40 foot catamaran, and my goodness, it was amazing! It had 2 full bathrooms with showers and toilets, 3 bedrooms (one of our friends took a nap), a full kitchen with oven, stove, sink, 2 freezer/refrigerators fully stocked with everything you would need to prepare and serve food and drinks. Bring your own ice though! You can purchase food or drinks before you go, or can bring your own for free, so that's what I did. I prepared a charcuterie board and other snacks and they had cute serving platters available. I made painkillers and there are cups, but I brought my own. There is an adorable comfy seating area inside if you get hot and you still get all the views with all the windows that open up as well. The outside has a covered area in the back with a large table. The front has the trampolines and little seats at the front. This boat had it all. It was new as well, completely furnished, and decorated stylishly. Our captain was really nice and did his thing without being too into our little party. The only thing that wasn't 100% perfect was that the anchor got stuck and wouldn't anchor, but with the caption and some of our guys' help, we were able to anchor so we could swim and check out the sand bar. I'd do this again and again! read more

See all

My wife and I completed the 2 day Cruising Catamaran Sailing course instructed by Scott Bruce. We learned and were tested on many skills relating to sailing and operating multihull sailboats. I found Scott to be both knowledgeable and patient in teaching the class. I feel that after successfully completing the course I am adequately prepared for chartering a cat or maybe even owning and operating one some day. If I had to offer one area of improvement for the class I would suggest adding a day on the course to include sailing in open sea conditions. There just wasn't enough time available to get all the critical skills in in a 2 day period. The limited time spent sailing was in crowded inter coastal waters. Thank you St. Augustine Sailing and Scott for making our experience so enjoyable. read more

I had such a great experience with St. Augustine Sailing! Their team members are friendly and professional and their sailing experiences are very luxurious! I hope to go back soon. Photo credit: Kayla Tuckerman. read more

Had an amazing time on 40 foot catamaran! Captain & Skipper both amazing. I have rented many boats in past but this was definitely one of the best experiences! Ordered the food through them too. It was great spread!! read more

We took a private charter cruise, which was our first time on a sailboat, and everyone at St. Augustine Sailing made this such a memorable day. Dale our Captain was fantastic! Thank you St. Augustine sailing, we will definitely be back to sail again! read more

I completed my ASA 103 with Captain Jeff. It was a wonderful experience! He was so attentive to the students and ensured we had time to learn the things we were struggling with while moving quickly over the things we understood. This was a really enjoyable way for me to learn. Scheduling was a little difficult since the online calendar isn't totally accurate but I was thankful for their flexibility. read more

Awesome private sunset sail with Captain Chris and Jay. Both great guys and the sail could not have been better. read more

St Augustine Sailing - Boat Charters Near Me - St. Augustine, Florida

We sailed for our first time with an excellent and friendly instructor. No pressure sales, just a relaxing ride on the ICW while we learned the parts of the sailboat, raised the sails, and tacked back and forth. Definitely do this again in the near future. read more

My husband and I booked this private sailboat for our anniversary on our st Augustine trip. We showed up on time and they couldn't find the captain! He was supposed to check in 30 Mins prior and he was no where to be found. The front desk guy called his boss who also tried to find the captain... no go! After 20 mins I was told sorry and if I want to return tomorrow we could sail and they would throw in a bottle Of wine. A bottle Of wine?? That's it? No discount? No thanks that's a horrible way to try and get a customer after such a mess up! so we passed. read more

I could not be more disappointed. no safety briefing. the captain was not hospitable. over the 2 hrs he only sailed for about 30 minutes and not exciting. it would have taken so little effort to make it a great day, but we never felt welcome on board. read more

We had the best experience with St. Augustine Sailing. Our girls weekend kicked off with a 2 hour sip and sail. Our captains were so nice and accomidating with music and taking photos . The boat was clean and had our pre-selected drinks on ice for arrival. The office was wonderful changing our reservation to a different day due to weather. We would highly recommend using this company! read more

Awesome intro for my gf - did asa 101 over the weekend. She went in nervous and unsure of her capabilities and came out a badass.

This was a very relaxing time. Wine and charcuterie were a nice addition. The boat was new and very beautiful. I would recommend this trip. read more

Captain Sarah did a wonderful job and the entire experience was just fantastic. Gave my wife an experience for her birthday that she will remember for years to come. I will look at sailing again for a relaxing time on the water. We are currently planning our next excursion and will be sure to book with them again read more

See all

Great people, boats, and instruction. Highly recommend taking ASA courses here if you want to start sailing.

Sorry that this is such a bad review. The various captains I've sailed with have been amazing. I took various STA courses and had to do the exams later because of health. Even though the contract says I can take the exams anytime, they tried to charge me hundreds of dollars to take something I'd already paid for and wouldn't budge. Then I booked a sailboat to take out one day and when coming to the dock to check out the boat no one turned up. They did offer me another day, but my friends (traveling from Ireland) had gone and the moment had passed. I'm just very disappointed in the school which is such a shame as the captains are the best I've met. read more

We booked a private sunset sail tour on the "French Kiss" for our date night. What a great few hours! We stopped and picked up some take-out and wine to have on-board. We just sat back, relaxed and let the breeze and waves do their thing! What a surprise that the captain even came prepared with a romantic date night play list. The tunes were nice and low in the background so we could still hear the birds and listen to the waves. read more

See all

The boats were all new and beautiful. We did a private 2 hour sunset cruise and it was so peaceful. My husband and I had a wonderful time.

You WANT to get introduced to SAILING! This is the pefect place to do that. I have some limited experience with nautical adventures on motor driven boats, but sailing was something i always wanted to try. Captain Mihai Cosereanu showed us the ins and outs of boarding the sail boat and what to expect when keeling. The time taken to introduce us to the basic nautical terms and techniques was very valuable. If you have any experience with motor boating, you will definitely enjoy this different vantage of boating. The winds we experienced were a gusty 10 to 12 mph, so that led to a lot of tacking heading away from the harbor, but on the way back, it was a nice leisure trip. There was a party of four, (please bear in mind that it usually requires a party of two or more students to attend with the captain, for there to be a class.) on our "sloop". Captain Mihai was excellent in defining conditions in weather, what to expect with different sailing vessels, and how to notice changes in current. Captain Mihai answered any question you had, and did his best to address any concerns and get you up to speed for future courses. Carol Ellis was excellent letting me know what to expect for later courses and the convenience with becoming educated with sailing. The staff was very hospitable and friendly. This was a great introductory course for me, since the only vessels i've been were under motor power. Wind power was awesome, and it didn't seem like we took up 2hours...but we did and enjoyed it. Most importantly, this didn't feel like I was going to school, but hanging with a buddy down the block on his boat. I loved that! read more

beware bad business! we gave a $100 deposit, my husband got sick the night before with a bad cough, we emailed them twice and called in the morning. they said no refunds, and ran our card after the phone call for the rest of the balance...and we are professional locals! read more

Loved our catamaran tour with Captain Jimmy. We saw dolphins and got to enjoy a nice swimming spot to ourselves. Plus Captain Jimmy was very knowledgeable on the area and made sure we caught the cannon firing from the fort. Capt Jimmy made certain everyone from the adults to the kids were entertained and informed. Highly recommend! read more

Loved sailing with St Augustine Sailing! My parents were in town and we scheduled a charter for a very relaxing and memorable experience. The captain was knowledgeable and enjoyable to be around. read more