Sail Jax Charters

We had the best experience with Sail Jax Charters for our engagement photos. From the start, Chelsey made scheduling so easy and was incredibly flexible when our original date looked like it was going to get rained out. Once we got on the boat, Shephard was phenomenal. He made Ciana and me feel comfortable right away, kept the evening fun and relaxed, and did such an amazing job positioning the boat so we could capture the best light and scenery. You can tell they truly care about creating a special experience. We’re so grateful for the memories and couldn’t recommend Sail Jax Charters enough!

Perfect way to end our vacation! From the moment I booked our 3 hour private sailing until the end of our sailing, both Chelsey and Shepherd were very attentive and accommodating! ⛵️ Shepherd was our captain and he made us feel right at home from the moment we stepped on the sailboat. My family enjoyed hanging out around the boat sightseeing and watching the sunset…🌅 Towards the end of our sailing we even got a bonus and got to watch the shuttle rerun, couldn’t have asked for a better night before we left the next day! 🚀 If you are visiting or a local I highly recommend booking a sailing with @sailjaxcharters!

We planned this trip as part of our quarterly therapist self-care retreat, and it exceeded every expectation. Shepard, Chelsey, and their sweet pup Pongo were the perfect hosts—warm, welcoming, and respectful of our space. Their energy set a relaxing and positive tone for the entire experience. The boat itself is stunning—immaculately clean, beautifully maintained, and thoughtfully designed inside and out. We appreciated having space to store our own food and drinks, and they generously provided water, ice, and paper goods as well. The scenery was breathtaking, and Chelsey was kind enough to capture amazing photos and even videos of dolphins for us. It was truly a 10/10 experience. We’ll absolutely be returning!

A wonderful way to spend time with family and keep everyone ages 15 to 80 entertained. We spent an incredible late afternoon with Captain Shepherd, Captain Chelsey, and their adorable pup Pogie. We had perfect weather chasing dolphins and taking in the gorgeous Florida nature. Chelsea and Shepherd were welcoming and accommodating and the Adelaina Mae was spacious and well-appointed. We will be booking again!