Sail Jax Charters - Jacksonville Beach, Florida

Melanie T.

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!

lindsay A.

We had an amazing experience with our family through Sail Jax charters. It was a great way to get out on the water and enjoy the beauty of Jacksonville while we were on vacation with our two small kids. Sailing with two small kids, Chelsey and Shepherd ensured safety was a priority. The boat is beautifully redone and well maintained. It has multiple bedrooms which was a selling point so my 1 year old could take a nap. Highly recommend this team!

Megan L.

We had an absolutely wonderful experience on this sailboat! The captains were not only incredibly knowledgeable but also fun and engaging, making the entire trip a delight. They shared interesting local insights, which added so much value to our sunset adventure.

The motor sailboat itself is impressively spacious with three comfortable bedrooms, two bathrooms, a galley, and a cozy salon, it felt like a luxurious floating home. The three outdoor decks provided plenty of space to relax, soak in the sun, and enjoy all the intracoastal views.

Julianna G.

Repeat customer here! The boat is huge and has multiple decks for viewing and a spacious indoor cabin (plus air conditioning!). I often get seasick but didn't feel nauseous at all thanks to Captain Shep's piloting! He is super knowledgeable about the waterways and shared so many cool stories about the Jax coast. Captain Chelsey made us feel so welcome! We love the Sail Jax crew! 🙂

Samuel M.

Captain Shep & Captain Chelsea run a top notch sailing charter in Jax Beach, Fl. They are knowledgeable about the history of the area, natural history, wildlife experts and will put a trip together for you and your group that you will not forget. The boat is exquisite and incredibly comfortable with all the modern comforts & its charm will make you want to hop aboard again tomorrow. Not to mention they are both super fun local folks!
Give them a call and book your sailing experience - you will not regret it.

I for sure will be back aboard this boat asap!!
Captain Samuel Moseley

michael B.

Sail Jax Charters is absolutely incredible, and Shepherd and Chelsey are the ultimate dream team! Shepherd is like the Gandalf of sailing—calm, wise, and always in control—while Chelsey is the queen of good vibes, making everyone feel like family within minutes. Together, they create an experience that’s equal parts relaxing, adventurous, and downright hilarious.

From Shepherd’s witty commentary to Chelsey’s next-level hospitality, every moment was unforgettable. They work together like a perfectly choreographed dance, making sure you feel like royalty while gliding through the water. If you’re on the fence about booking, just do it—you’ll laugh, you’ll relax, and you’ll probably want to become a sailor by the end. 10/10, Shepherd and Chelsey, you’re legends!

Brandon C.

What a fantastic evening! This was the perfect sunset cruise for our extended family. From 1yo baby to grandma and grandpa and everyone in between, everyone had a great time! The crew was accommodating and catered to our every need. If you are looking for a great day/evening out on the water look no further!

Spencer D.

Chelsey and Shephard did such a beautiful job restoring their sailboat and created such a special experience for our private sail for our anniversary. Highly recommend! Plus, their puppy onboard is the cutest passenger.