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    Windward Sailing

    5.0 (20 reviews)
    Closed 8:00 am - 10:00 pm

    Services - Windward Sailing

    Boat charters

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    Sailing the Cumberland sound.

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

    Jewell W.

    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!!

    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

    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!

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    10 months ago

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    2 years ago

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    2 years ago

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    11 months ago

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

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    2 years ago

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    9 years ago

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    Ask the Community - Windward Sailing

    Review Highlights - Windward Sailing

    The booking process was easy and our captain, Captain Steve, was extremely knowledgeable and professional.

    Mentioned in 10 reviews

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    Lucky Dolphin Tours - Look at all that poop

    Lucky Dolphin Tours

    (7 reviews)

    Beaches

    We absolutely loved this tour and experience. Max 6 people on a boat, we were 4 and no one else…read morebooked so it was totally like a private tour. Price is worth it for the comfort and private experience. Owner is totally chill, surfer guy vibes, very friendly and very knowledgeable about sea life and dolphins with years of experience. You can tell he loves what he does and is passionate about his business. He brought us out around until we found a huge swarm of dolphins and we just followed them the whole time. There was a tonnnnn of them. Didn't see manatees this time but I don't think they are as common as the dolphins as that's where the dolphins live and reside. It was a great way to start your morning and my 8 year old son absolutely loved it. We don't support seeing dolphins in captivity and he also explained how horrible it is having them in captivity. This is a great way to experience seeing dolphins without the exploitation of dolphins. Highly recommend and would absolutely do this again if I came to town again.

    I cannot say enough good about our tour. Captain Dustin was so personable and knowlegable. He…read moreinteracted so well with the kids and made the tour not only educational (which it was - VERY!) but so fun too. We saw MANY dolphins and he could spot them far off and would steer right over there and point out where we should look. He has a good sense of humor is professional in conduct and in speech, which I appreciated very much too. If you could give a score of 10 star, I would definitely give it 10!

    Windward Sailing - boatcharters - Updated May 2026

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