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    St Augustine Sailing

    4.6 (40 reviews)
    Closed 9:00 am - 8:00 pm

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    Services - St Augustine Sailing

    Boat charters

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    Acting like I know what I am doing.

    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.

    Jose G.

    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!

    Elise G.

    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!

    Mark M.

    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.

    Wing on wing

    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.

    Getting some sun!
    Lisa M.

    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.

    Sea treasures we found when we walked the sandbar

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    2 years ago

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    Rose Ann P.

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    1 year ago

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    Rose Ann P.

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    8 months ago

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    Rose Ann P.

    Thank you so much!! We are so happy you all had a great time.

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    5 months ago

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    Rose Ann P.

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    3 years ago

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    Rose Ann P.

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    3 years ago

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    Rose Ann P.

    Thank you Elise

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    1 year ago

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    Rose Ann P.

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    2 years ago

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    6 years ago

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    3 years ago

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    Rose Ann P.

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    4 years ago

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    2 years ago

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

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    Rose Ann P.

    Thanks for the great review. We are so happy you enjoyed the sail.

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    2 years ago

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    2 years ago

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    Rose Ann P.

    Wonderful news! Thank you so much for sharing!

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    3 years ago

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    Rose Ann P.

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    2 years ago

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    Rose Ann P.

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    5 years ago

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    3 years ago

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    Rose Ann P.

    Thank you so much!!

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    3 years ago

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    5 years ago

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    Rose Ann P.

    Kayla - Thanks for your kind words!

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    3 years ago

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    Rose Ann P.

    Thanks Isaiah. We enjoyed having you here with us.

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    3 years ago

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    2 years ago

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    6 years ago

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    Rose Ann P.

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    2 years ago

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    Rose Ann P.

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    3 years ago

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    4 years ago

    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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    5 years ago

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    Rose Ann P.

    Thanks for sailing with us!

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    5 years ago

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    Rose Ann P.

    Thanks!

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    4 years ago

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

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    7 years ago

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    Rose Ann P.

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    7 years ago

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    4 years ago

    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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    3 years ago

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    14 years ago

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    8 years ago

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    13 years ago

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    Ask the Community - St Augustine Sailing

    Review Highlights - St Augustine Sailing

    We did the ASA 101-104, We worked hard and laughed hard, both instructors were very thorough and had lots of patience.

    Mentioned in 5 reviews

    Read more highlights

    Red Boat Water Tours - Floating along downtown.

    Red Boat Water Tours

    (142 reviews)

    Ignore all the other boat tours and book your tour with Red Boat. So glad we did. We did the BYOB…read moresunset cruise. Captain Dave and his first mate Vicky were great. Dave was so informative and accommodating. And inwant to be Vixkys friend lol. We were offered complimentary ice cold waters. Boat was roomy and very clean. There was a restroom on board. They offer other tours. We will be back for Christmas lights tour.

    I scheduled a sunset cruise with Red Boat Water Tours last September for me and two friends who's…read morebirthdays were in the same week. My friends missed the boat lol! So we rescheduled for mid-May. This time, everyone made it;))) We arrived a few minutes before the boat launched. It was extra crowded as we were told another tour company cancelled, so they let those customers on our boat. It was tight, but we were ready for some fun! We were moving along on Matanzas Bay about 10 minutes. I went to the restroom and noticed some open space in the back of the boat. I went back to the front and got me friends and that's where we hung out the remainder of the boat ride. I'm not a fan of restricted space, so this move felt great! We saw dolphins and an amazing sunset. We went under the Lions Bridge, went by the St Augustine Lighthouse and Castillo de San Marcos. I can't explain how absolutely perfect the weather was that night. But if I go again, I will choose mid-May! Not too hot or humid. The staff was fabulous and friendly! Don't forget to tip them when exiting the boat.

    St Augustine Eco Tours - Kayaking at the fort

    St Augustine Eco Tours

    (67 reviews)

    We booked a private eco tour for our party of 6 as a Mother's Day gift. We had the pleasure of…read morehaving Captain Zach as our guide with the assistance of Captain Kevin. We all had an amazing time. Zach is very passionate about the preservation of this beautiful area and all the wildlife that lives here. He's incredibly knowledgeable and happy to answer any and all questions... even the ridiculous ones...lol. He interacted so well with our two daughters who are 4 and 10, but was sure to engage with everyone on the boat so we all got a personalized experience. We saw so many dolphins and birds (the spoon bills were a special treat for us) which was our main objective. The boat itself was very comfortable and they were happy to accommodate our boat with an extra shade to keep my Mom more shielded from the sun. He also offered to take us out a hour earlier than the advertised time of 11 a.m. so that we could try to beat the heat, again to accommodate the older guests on the boat. Our girls had the best time taking their turns driving the boat and he even treated them to shark teeth after the trip because he heard us talking about shark teeth hunting and we had asked him about secret spots to look for them. Captain Zach is just an easy going guy with a lot of passion and expertise that he loves to share. Having that kind of person as our tour guide really made the experience for us. Overall just a fantastic time. Worth every penny to get a private tour. 10/10 experience!

    We had a wonderful time on our tour with Chris! He was very knowledgeable about the area and he…read morecatered our experience to what we wanted to see. We booked a private charter and I can't recommend it enough! We've done the regular tours, too, and they are great. We love this company and recommend it often. Just book it!

    Sabrage Charters

    Sabrage Charters

    (11 reviews)

    I booked a sunset cruise with Sabrage in St. Augustine to celebrate my brother and sister-in-law's…read more33rd wedding anniversary. With a perfect 75° evening forecasted for a Saturday night, it seemed like an ideal way to enjoy the occasion. Their online booking system was easy to use, and after our credit card was authorized, we were all set for a 5:00 PM departure. Unfortunately, when we arrived at the dock, things took a disappointing turn. The business office was open, but no staff were inside. After asking around at nearby boats, we learned that no one from Sabrage had been seen all day. I called the number provided, only to reach voicemail. About ten minutes after 5:00, I finally received a callback informing me that they had simply overlooked our reservation and did not have staff available to run the boat that night. It's incredibly frustrating to book an event on a Friday, only to show up the next day and find out that the company didn't even check their reservations. Based on other reviews, it seems like the cruises themselves are enjoyable, but the lack of organization and reliability is a major red flag. If you do choose to book with them, I highly recommend calling ahead--maybe even more than once--to confirm that they're actually operating. To their credit, they voided the charge quickly, but the overall experience left a lot to be desired. On a beautiful Saturday night in March, in a prime tourist location, I can't understand why a cruise company wouldn't be running. If not then, when? Given this experience, I have no plans to book with them again.

    We had a terrific experience with Glen! Everything was perfect and we had a great time! Highly…read morerecommend!

    St Augustine Sailing - boatcharters - Updated May 2026

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