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    Adventure Sailing Tours

    5.0 (4 reviews)
    Open 8:00 am - 9:00 pm

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    Boat charters

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    Jolly Sailing & Dolphin Cruise

    Jolly Sailing & Dolphin Cruise

    5.0
    (129 reviews)

    We had the absolute BEST time on the Jolly Sailing & Dolphin Cruise!! I serve at a hotel restaurant…read moreon Pensacola Beach, and I can honestly say I will be recommending this to every single guest from here on out--it was THAT good. Mary was our tour guide, and she was truly something special. I wish I remembered the captain's name because he was so kind and welcoming too, but Mary completely made the experience unforgettable. She went out of her way to connect with every single group and person on the boat, and especially the kids. You can tell she genuinely loves what she does, and it shows in every little interaction. My son is 3 and usually stays to himself, but Mary picked him up, let him ring the bell, and everyone cheered for him--it was such a special moment that I'll never forget. As a mom, that meant everything* to me. The whole experience was so fun and interactive--we were waving or dancing every time we passed another boat, laughing nonstop, and just genuinely enjoying every second. The vibe from start to finish was so light, happy, and comfortable. The boat itself was super nice & spacious with comfortable seating, plus you could see everything from every angle, which made it easy to catch every encounter! Pro-Tip: come prepared with your best dolphin puns and your "dolphin call" because they WILL put you to the test This was hands down one of the best experiences we've had on Pensacola Beach. We will definitely be back, and I truly can't recommend it enough!!

    We booked this tour through Viator a few days in advance. The team communicated ahead of time that…read morethe departure time could change or even be canceled due to weather. Our tour ended up being moved to an earlier time the day before. I did receive a couple of different text messages about the start time, which caused a little confusion on my end, but the crew communicated well and kindly waited for us before departing. The address synced perfectly with the gps to the exact departure location. Parking was free and available immediately by the dock area, but notes this will likely not be the case during peak tourist season. The tour itself was lovely. We had beautiful weather, and the crew was attentive and knowledgeable, sharing interesting history and stories about the bay throughout the ride. We saw dolphins and were able to capture plenty of videos and photos. This would be an especially beautiful tour to take in the evening to enjoy the sunset.

    Condor Sailing Adventures

    Condor Sailing Adventures

    5.0
    (69 reviews)

    I cannot say enough wonderful things about Captain Kirk and his incredible Condor 40 trimaran,…read more*Dare II*! We took our three girls (ages 3 to 8) on a dolphin tour with Condor Sailing Adventures, and it was easily one of the highlights of our trip and one of the best family experiences we've had. I'll admit, as parents, we were a little nervous when we saw the "don't get seasick" disclaimer. I mean... seasickness isn't exactly something you choose. But Captain Kirk and *Dare II* put those worries to rest immediately. This boat is basically the Ferrari of the ocean. It's unbelievably smooth and stable. Even our youngest stayed happy the entire time, laughing, pointing out dolphins, and having zero tummy troubles. I've never experienced anything quite like the way *Dare II* glides across the water. Captain Kirk was fantastic--knowledgeable, patient, and genuinely wonderful with kids. He made the whole experience feel personal, relaxed, and fun while making sure everyone felt safe and comfortable. We saw so many dolphins up close, and the small group size made it feel special instead of crowded and touristy. And then came the surprise that absolutely made our girls' day. At the end of the tour, Captain Kirk let each of them take a turn at the helm and "drive" this Ferrari of a boat (with his close supervision, of course). Their faces lit up like it was Christmas morning. Watching them steer *Dare II* was the perfect ending to an already magical day. If you're looking for a truly special, family-friendly experience in the Pensacola/Gulf Breeze area, this is it. Captain Kirk and *Dare II* are in a league of their own, and we're already talking about when we can come back.

    Dare II Experience! We sailed past boatloads of tourists and enjoyed our own personal captain…read morewithout charter prices. Captain Kirk let each of us take our turn at the tiller, chased and watched some dolphins, provided drinks and snacks, and shared some of his experiences as a professional racer on a unique 40-foot Condor racing trimaran. Racing before the wind, relaxing in adjustable recliners, sitting up on the pontoons watching the water speed by underneath and enjoying the sun & salt spray made for an unforgettable day! Are you ready to take the Dare II?

    Adventure Sailing Tours - sailing - Updated July 2026

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