Highly recommend this sailing experience! They were super accommodating and Captain Benny was amazing! I’ll for sure use him next time I come down! You WILL NOT be disappointed!!!!

Benny was a FANTASTIC tour guide! My family and I loved our 2-hour trip. I highly recommend - booking was easy! We saw dolphins and wild horses ❤. Thanks Benny!

I chartered a 34 hunter from Windward Sailing this spring break. My wife, two daughter and myself enjoyed 4 days sailing Cumberland, St Marys and the ICW. It is such a beautiful area. Plenty of transient sailors this time of year but still ample room. It is surprising that there is not more bareboat charting availability. I had to search quite a bit before I came upon Windward sailing and its owner Tony. Im glad I did! Tony is very nice, knowledgeable and accommodating. He made out charter a great experience. Thanks Tony!

What a great experience! We decided to check into taking a brief boat trip during our trip to Amelia Island, but were wary of being on a crowded vessel right now. We are thrilled to have found Windward! Tony was so accommodating of our last minute request, and Captain John did an *outstanding* job during our tour. He was safe, knowledgeable, and very engaging. Our sons LOVED learning some sailing basics from John... It was definitely a major highlight from our vacation. Our only regret was not having more time to spend on the water!

On short notice, we called and was able to be squeezed in no problem. We went out sailing for two hours with our family of four and had a wonderful time! The captain was very knowledgeable, friendly and funny. He actually let our oldest sail the boat for a while!! We even were able to see six dolphins before we came back to shore. It was an unforgettable time for our whole family! Our four year old and our thirteen year old thoroughly enjoyed it. I would recommend this to anyone and it is one of the more affordable things to do around the island as well!

We had a fun cruise with Capt. John. We definitely recommend Windward Sailing.

We scheduled a sail on short notice, and we were well taken care of. The 3 hr catamaran trip was fun and very informative with the area and the boat. We relaxed while watching sea life as the kids enjoyed laying out on front of boat.

Had a great day with John. So knowledgeable and perfect for my husband who is learning to sail. We had a wonderful time. Highly recommend.

Tony took my family on an unforgettable evening sunset Catamaran boat ride! The boat was clean & the staff was very professional. I highly recommend this company for a private boat tour!

My wife and I booked a last minute sunset cruise for our honeymoon. Our captain, John, was great and the event as a whole made for an unforgettable evening.

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.

I have taken several ASA classes with Tony and John. The school is very accommodating to my work schedule. Classes are small and thorough. All five classes I have taken have been fun with lots of time on the water. You can tell both Tony and John love to sail and teach. Windward sailing is a great company, and I look forward to taking more ASA classes with them.

Although we live in SE Georgia, my wife and I were both anxious to set sail after purchasing a used, but well maintained Catalina sailboat. We scheduled the back-to-back ASA 101 and 103 classes over a weekend and two days, and very pleased to have had John Drake as our instructor. John was great to work with through the in-class materials, as well as the time on the water. His knowledge of sailing made us so comfortable to be on the water for several days of instructional sailing. We were so pleased with his personality and style of instruction, we scheduled some follow up training with him for both of us. I would highly recommend any of of the available classes or charters that Windward provides.

Had an EXCELLENT time in Basic Keelboat 101. The instructor, John always made our time on the water fun and without incident, while more than preparing us for the exam, which all students passed easily. Johns relaxed way of asking you to make choices and assess the situation on the boat really cements the principles from the book without putting you on the spot. What a blast, highly recommend WINDWARD SAILING.

I came to Jacksonville to have memorable moments with my family, I left with memories that will keep a smile on my face for weeks if not months. tell them what u need and its yours....... good job captain your amazing. .. ps make him sing he will set the mood.. thank you for memories of a lifetime... :)

My husband and I took out the 265 Beneteau for an afternoon in September. The waves out on the Atlantic were pretty intense (plus 20 k winds) so we sailed in the Cumberland Sound and had a blast. Tony and Wayne were great!

My wife and I had a great time in ASA 101 class. Capt. Charlie was the best.

Had some down time and just wanted to go out sailing, excellent time, very enjoyable. Definitely would come back to Windward.

We chartered a sunset sail for our Anniversary with John on Sept 26th, 2015 and it was absolutely spectacular. We will definitely be back. Thank you for making our 15th Anniversary memorable.

A great family (2 adults and 2 kids (8 and 10)) trip with 2 days and 2 nights of sailing on the ICW. Captain Tony planned a fantastic voyage with lots of sailing and learning opportunities for all of us. A great eye opener to bareboat cruising and future adventures under sail. Would totally recommend windward sailing for any family looking to explore sailing and the ICW.

My boys and I did 101, 103 and 104. Loved it! Will be back for more!!!

Had a great time, very professional, highly recommend.

Great time!

Birthday Celebration for the books! Amazing experience. Captain John was an awesome sailor and guide and Im sure we are his favorite first mates! Our sunset sail was beautiful and I would recommend everyone cast off with Windward Sailing! I dont know much about boats but the vessel we were on was fantastic and also had a restroom! A++ dont miss out. Must do on Amelia Island. Oh, we got to see Fort Clinch