We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers: Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
We chartered a late evening two hour cruise and it was worth every penny. Captain John was very friendly, answered all of our questions and even let the whole family drive the boat. It was a fun eye opening experience in regards to sailing. I...More
Tony and Cindy from windward sailing gave us the most amazing afternoon. My husband and I booked a 3 hour sail for just the 2 of us . We had an amazing experience. This was our first sailing adventure. Tony and Cindy made it easy...More
My daughter and I thoroughly enjoyed our 2-hour sunset sail last night with Captain John on Windward’s monohull! I really thought it would rain on us, but the evening could not have been nicer. We saw jumping stingrays, several dolphins at various locations and even...More
My most recent visit to Windward Sailing School was in May, 2018 to complete my Bareboat cruising certification from the American Sailing Association. Previously I had taken two excellent sailing courses at Windward to receive Basic Boating and Coastal Cruising certifications. My most recent experience...More
I took the first three ASA sailing classes here on March in the early 2010s. I was thoroughly impressed with Tony Jones (the owner of Windward Sailing School at that time), the instructor he hired for part of the training when he was not teaching,...More
We took our kids and teenage grandkids sailing for a couple hours with Captain Tony. We were on a 37 foot Catamaran that was immaculate and in perfect condition. Chris,Tony’s wife, met us on the dock, got us settled in and went through the safety...More
Our family (13 and 11 year olds) had a fantastic time sailing! Captain John was friendly and easy going. We all got to steer and help in any way that we wanted. It was pretty windy (31 knots at one point) and we all thought...More
From the time you call to book your trip to stepping off the boat you are made to feel
First,the response time for booking is amazing. Shout out to Tony!
Second Captain John was amazing from his knowledge of the Island to the...More
Our family thoroughly enjoyed a private cruise with Captain John! We looked at a number of boating options and ultimately decided upon Windward Sailing as it was not commercialized or overly touristy like the other options available, which is much more enjoyable to us. Captain...More
A very special Girls Night Out was easy to host with Windward Sailing. Tony graciously made planning around 6 busy women's schedules a breeze. We enjoyed every minute with Captain John - whether he was highlighting Fort Clinch, spotting dolphin, or humoring our girl-talk! Confident...More