If you're looking for a relaxing, picturesque sail on the water with occasional moments of adrenaline-induced existential reflection--Windward Sailing is the spot on Amelia Island. The captain and his wife guided us across the open waters like a man born with a rudder for a spine. The boat was beautiful, the views were breathtaking, and the wind... well, let's just say my hair looked like I lost a fight with a leaf blower. At one point, dolphins swam alongside us, probably just to mock my sunburn. It was majestic. Magical. In short--10/10 would sail again. read more

Amazing trip and the owners are so Kind and attentive to every detail. I have always wanted to sail and the trip was great. Weather was not so great but the owners more than made up for it. read more

Cindy and Toni took very good care of us. We were a party of 10 ladies celebrating a 60th birthday. It was very special and love the journey. We took around Fernandina Beach and all the way up to Cumberland Island. Highly recommend this trip. read more

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Everything ! Loved our cruise ! Captain was great, friendly, safety focused, knowledgeable and very accommodating. Plan to do again !

The most relaxing and enjoyable experience with sightings of dolphin and wild horses on Cumberland island! read more

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Our bachelorette party had a great time on the catamaran cruising the river with Windward Sailing! Tony was very helpful with the booking process and gave us the information we needed. I had never booked a private boat before, but we were so glad we did this instead of the larger public group charter we were looking at. Our captain was very friendly and helping us learn about Amelia Island. We brought our own cooler of drinks. Wish we had brought a speaker for music, but it was still a really fun time out on the water! Would definitely recommend to family and friends!! read more

Windward Sailing - Boat Charters Near Me - Fernandina Beach, Florida

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Fantastic captain that was knowledgeable and engaging. Great catamaran kept up well. The day was perfect for lounging on the trampoline, sightseeing wild animals including wild horses, and relaxing under the sails. read more

A friend booked this for my birthday and it was just perfect!!! Capt John was on time, boat was clean, he was knowledgeable and friendly and made all of us feel at ease. I had never sailed and feel like I have been missing out all my life! It was so much fun! It was a beautiful evening! Capt John let my 17 yo steer for awhile and she took to it naturally and I think she is a fan now also and I definitely see us back out there! Thank you so much Windward for an amazing experience!! read more

From start to finish my parents and I had amazing time sailing. John was our captain who was not only personable but taught us a little bit about the history of Amelia Island and of sailing itself, which was great!! He was a complete gentleman the entire time and refilled our drinks whenever needed and also unfortunately when it started raining was a true gentleman and making sure that we got back safely and as dry as possible. I would highly recommend Tony , John and the rest of this sailing company to anyone that goes to the area read more

Windward Sailing - Boat Charters Near Me - Fernandina Beach, Florida

We were looking for something different to do on our last day of vacation and called Windward Sailing last minute. Tony was awesome and fit us in within a few hours. My husband and I took our 3 and 1 year olds for the 2 hour private tour and it was absolutely perfect! Our captain was John, he was phenomenal. Our 1 year old was a little cranky and John was very understanding and patient with us. Our 3 year old had the time of her life. John talked to her, let her safely explore parts of the boat and made her day by letting her steer the boat. This was the highlight of our trip, I can not recommend more! read more

Windward Sailing - Boat Charters Near Me - Fernandina Beach, Florida

I signed up for the 6-day combo of ASA 101, 103 and 104 and completed them 23 through 29 November, 2018. In the 101 course there were four students. The instructor was Michael. He was very knowledgeable and experienced. The course was taught on a 28-foot Hunter. The group size was good, but more than 4 would be too crowded. We spent a couple hours reviewing material Friday evening and then a day and a half on the water with lots of practice with the basic maneuvers, docking, undocking and Man Overboard drills. This course was all completed in the inland waters of the ICW and St Mary's Inlet. The 103 course was taught by Tony, the owner, and he has amazing boat handling skills! He whips the boats around under power or sail with lots of confidence and precision. The boat was a 34-foot Hunter for much of the course, but because we damaged a sail on the 34-foot boat we did use the 28-foot boat for docking and undocking practice. There were only three of us for this course and that was a great class size. The 103 course was a great continuation of learning coming off the 101 course. Not only do you use all those basics, but your on a bigger boat with different equipment and handling characteristics. We were able to spend some fun time on the ocean and experience stronger winds and heavier seas. We also had some commercial shipping traffic to help us exercise the Rules of the Road. The docking and undocking training was a great part of the course. Building on the basic course we took the boat in and out of the marina several times, maneuvering between docks, backing in and out of slips, turning around between docks, etc. The maneuvers in the marina is something I would be very nervous about without this training. There are lots of YouTube videos of people with poor yacht handling skills in the marinas and I don't want to be in one of them! The 104 course was taught by John and he used his personal Westsail 39 for the course. Sailing on John's boat provided a great opportunity for me and the one other student in the class because we gained experience handling a much larger boat with a vastly different equipment configuration and handling characteristics. We were on the boat for about 48-hours. The first day we boarded in the afternoon, sailed for a while and then took the boat to an anchorage near the St Mary's Inlet. The lectures/course material review was held onboard the boat while at the anchor or dock. We ate the slept onboard. In the morning we sailed to Jacksonville. The wind was strong and the seas looked pretty rough, but the boat handled them very well. We docked at the public dock near the Sister's Creek boat ramp. In the morning we motor-sailed or motored our way up the ICW. John was a great instructor and a fantastic host. The meals, conversation and sharing of knowledge were fantastic! Following each course there was a 100-question multiple choice exam. Reading the books ahead of time is definitely a must in order for all students to benefit from each others participation. If you don't read the books you may demand more than your fair share of the instructors time and you may not be knowledgeable enough to understand what the instructor is trying to teach. Overall I had a really great experience learning to sail from Michael, Tony and John. I highly recommend Windward Sailing to anyone considering learning to sail. read more

Decided to take this sail for an anniversary trip. Just us and the Capt and his wife on the cateraman. Had a great relaxing time. Scenery is factories for the first half and beaches for the second half. Great couple and great experience. read more

John is Great teacher and a fun guy. Very patient. Quickly felt like a friend. Knows the local waters like the back of his hand. Highly competent sailor. Tony was with us for a morning and was equally good. We've sailed for years and John molded the course accordingly. I highly recommend Windward Sailing. read more

Took the intro class this past weekend, loved it! Captain Tony is very knowledgeable & friendly. He really takes the time to explain everything as you sail, I learned a lot in 3 hours. In addition, he's familiar with the area and pointed out interesting sites along the way. We saw beautiful birds, jellyfish, the ruins of the Carnegie mansion, and wild horses. I'd definitely sail with Windward again, and I recommend them to anyone interested in sailing!! read more

Windward Sailing - Boat Charters Near Me - Fernandina Beach, Florida

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We had a great time. Much better than a big tour boat. Was just the two of us and our captain on a two hour sunset cruise. Nice boat. I think it cost 175. Well worth it. Captain John was great. The three of us just shot the breeze for two hours and sailed around at sunset. Was gorgeous. read more

Amazing day learning to sail a 32 foot sailboat from Florida to Georgia on the inter-coastal. Coleman, our captain and instructor, was personable and knowledgeable. He really made our experience both educational and enjoyable particularly considering the 40 degree weather. Highly recommend them if you are considering adding sailing to your repartee. read more

We used Windward Sailing to celebrate a birthday while in town for a wedding and had an awesome experience. The booking process was easy and our captain, Captain Steve, was extremely knowledgeable and professional. We even saw pods of dolphins and wild horses! Only wish we had booked for three hours instead of two. read more

The sailing classes that they offer are great! We had so much fun, learning a lot over a short period of time. I took the 6 day class for levels 101, 103, 104 during low season. There was one other student who attended all 3 levels, and a third one who attended 103 and 104. 101 was taught by John, 103 and 104 by Tony, the owner. They are both extremely kind, patient and smart. Tony is amazingly tech savvy: he would check the tides, weather forecast and boat speed from his iPhone. And most importantly, you can tell they truly like teaching. After taking 101, we could maneuver the sailboat around the marina. 103 taught us how to read charts and recognize landmarks for navigation and gave us further sailing practice. 104 was about navigating in rivers and at sea, anchoring, doing basic servicing and many other useful skills. The training format is roughly 8 hours of sailing per day, classroom classes (~1-2 hr/day, sometimes done on the boat in the cabin), and one written exam per level every 2 days. During 104, you will sleep on the boat for 2 nights. read more

Wow!!! Just finished up THREE days of sailing with Windward Sailing at Amelia Island, FL. Talk about fun!!!! One couldn't ask for a better mini-vacation! Thursday and today we went out with Captain Wayne. GREAT GUY!!! Sailed in Cumberland Sound and the channel leading out to the Atlantic Ocean. Yesterday we went out with Capt. Tony, another great skipper (and owner of the company) and sailed through the channel to the ocean, was able to see a deep draft vessel (submarine) escorted in by gun ships, and schools of jelly fish. As I said, this was a great time and Tony and Wayne are great captains and I would recommend Windward Sailing for cruising like we did OR their ASA certified sailing classes. read more

Captain Tony makes these sailing trips. He knows his stuff about sailing and the local area. He also is a great teacher and communicator. It is a beautiful and challenging area in which to sail, and it makes it even better that the captain provides great service. Whether you want to learn how to sail, brush up on your skills, or just enjoy a day out sailing, you won't be disappointed. read more