Windward Sailing

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 it's owner Tony. I'm 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!

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.