St Augustine Sailing
Sailing school · St. Johns County ·

St Augustine Sailing

Sailing school · St. Johns County ·

Luxury private sailing charters, instruction & team building events

St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null
St Augustine Sailing by null

Information

3076 Harbor Dr, St. Augustine, FL 32084 Get directions

Information

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3076 Harbor Dr, St. Augustine, FL 32084 Get directions

+1 904 829 0648
sta-sail.com
@staugustinesailing

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Last updated

Nov 28, 2025

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20 Best Things to Do in St. Augustine, Florida

"A charter operator offering sunset sails and other excursions that deliver romantic, postcard-worthy views of the coastline—options include brunch sails or dinner cruises that can feature a private chef for a more luxurious outing." - Skye Sherman Skye Sherman Skye Sherman is a travel writer based in West Palm Beach, Florida. Aside from traveling, she's also a pilot, scuba diver, bookworm, and fourth-generation Floridian. Her work has appeared in Travel + Leisure, USA Today, Palm Beach Illustrated, Atlas Obscura, and more. Travel + Leisure Editorial Guidelines

https://www.travelandleisure.com/best-things-to-do-in-st-augustine-7563870
St Augustine Sailing

Andrzej L.

Google
Two weeks agou I had an excellent experience learning to sail (ASA-114) with Captain Nuri Yaylali. He was very communicative throughout the process, making sure I understood what to expect before we even got on the water. His teaching style was clear and easy to follow, breaking down complex maneuvers into manageable steps. I always felt confident about what I was doing thanks to his patient explanations. I'd highly recommend him to anyone looking to learn catamaran sailing.

Her Majesty The Q.

Google
We had an absolute blast on our Sailing charter! The crew was very well prepared for us. The boat was immaculately clean and well-stocked with everything we needed. We were celebrating a special birthday for one of my husband's oldest friends and wanted to make it special. This was such a great way to go. Easy to get in and out of, with designated parking on site and friendly and attentive staff from the first interaction to the last. Beautiful sunsets and some dolphin spotting too!

Katherine K.

Google
We had such an amazing time at the Sip & Sail! We ended up being the only couple who made a reservation so we had the trip to ourselves. The wine was delicious, the views were amazing, and Kevin and Max were an amazing captain and crew!

Takiya L.

Google
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!

Norm B.

Google
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

vicki “joviha1957” H.

Google
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!!

Andy O

Google
⛵️ 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! 🌊⚓️🎉

Dan S.

Google
Had a great experience taking my ASA 114 catamaran course at St Augustine Sailing! The entire staff was friendly and professional. Our instructor Nuri was excellent. He covered everything thoroughly and made everyone feel confident in their sailing skills. The boat was in great condition, and the weather was perfect for sailing. Great place for beginners or advanced sailors to enhance their skills.

Coy M.

Yelp
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.
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Safura O.

Yelp
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

Cecelia R.

Yelp
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!

G H.

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

Cyndi T.

Yelp
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
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Jose G.

Yelp
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!
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Elise G.

Yelp
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!
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Ian S.

Yelp
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.
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Mark M.

Yelp
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.

Eric S.

Yelp
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.

Chris H.

Yelp
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.
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Chanthry N.

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

Yelp
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.
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Markus L.

Yelp
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!

Jackson D.

Yelp
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.
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Ross P.

Yelp
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.

Vicki W.

Yelp
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!

K D.

Yelp
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.

Ed B.

Yelp
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.
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Zahra U.

Yelp
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!!
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Jeff D.

Yelp
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!
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Isaiah T.

Yelp
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.
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Rachel E.

Yelp
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!

Jim G.

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

Bruce W.

Yelp
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.
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Kayla T.

Yelp
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.
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Hanna S.

Yelp
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!
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Melissa A.

Yelp
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.
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Ewan O.

Yelp
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.
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Jessica G.

Yelp
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.

Steven H.

Yelp
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

Dan T.

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

Yelp
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.

Melissa S.

Yelp
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.
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Tena C.

Yelp
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.

Thomas K.

Yelp
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!
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Charles g.

Yelp
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!
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Cory D.

Yelp
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!
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Carolyn M.

Yelp
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.
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Must Be Nice V.

Yelp
If you want to learn how to sail (or just go along for the ride), Captain Jim Gilbert is excellent! He is a great instructor with an equally great personality! Beginners to experts will love sailing with Jim!