My wife and I recently came back from a trip where we completed an incredible 5 days with Captain Brad on his 30’ Catalina. I completed ASA 101, 103 and 104 and my wife did ASA 101. I’d sailed dinghys in the past, but Captain Brad took me from zero to 100 on keel-boat sailing. Captain Brad is knowledgeable, …and very patient teacher. He knows the waters in the area very well which helped calm my wife when we got out into the open water. We had mooring practice, charting, sail trim, managing winches and more. The BEST was our overnight on the boat, I highly recommend doing that. Incredible sunsets and sunrises off of Mule Key with the Captain cooking and drinks under a full moon. I have the sailing bug after this trip.

I also wanted to express my gratitude to Brad and Sherry for being so flexible and accommodating a challenging personal situation. This trip was nearly 2 years in the making and we are so appreciative of Brad’s and Sherri’s flexibility and allowing us to reschedule when we had to.

We’re looking forward to taking future ASA courses with Brad as we have a lot to learn. He’s a treasure and sailed up and down the East Coast on his boat for decades and there’s an amazing world of knowledge to tap into. Brad maintains contact with many of his students as they start their journey’s on owning boats and planning trips. His knowledge of sailing Florida, the East Coast, and the Bahamas is invaluable. If you’re serious about learning to sail and charter, Captain Brad is the best-kept secret.

Just wrapped up an amazing sailing class with my husband and we loved the experience! Captain Brad was absolutely fantastic - super kind, patient, and made sure we grasped every bit of the course material. We felt so comfortable asking questions and learning at our own pace. By the end of the class, we were both confident with the course content. If you're looking for a sailing class that's both fun and informative, look no further. Highly recommend!

Just finished two great days of sailing with Capt. Brad! He did a terrific job of helping me sharpen my skills and teaching me some really helpful boat handling techniques. We also had plenty of exciting moments both days, including rescuing three people stranded in the water after they had been ejected from their powerboat, tacking against big tides and tough winds (gusting over 30), and watching the Blue Angels perform over Key West.
Hanging out with Brad was good fun — he’s easy to talk to, and he knows lots about the area. Highly recommend his sailing school.

Because of Captain Brad we love sailing!

We had no sailing experience prior to taking the ASA 101, 103 & 104 courses at Southernmost Sailing School. Captain Brad's immersive teaching style on the water and thorough instruction of the book lessons made for quick uptake of a lot of information in a relatively short period of time. Also, while on the water, his concise instructions yet patient and calm approach in steering us through challenging maneuvers in tricky weather was invaluable in preparing us for future sailing adventures on our own.

Thank you, Captain Brad! We had a fantastic experience and enjoyed getting to know you and Sherri. Looking forward to joining your flotilla to the Bahamas someday!

Took the ASA 101 and 103 Classes with Capt. Brad in January 2025. It was fantastic. I wasn't sure what to expect, but Brad was Great! His whole approach to the classes was fantastic! We did have some challenges with Heavy Winds, but Brad worked it all out and we were able to complete our two classes in the days we had available! Very down to earth and knowledgeable. It was a great environment to learn to sail a larger boat! Highly recommend the school! It exceeded my expectations!!

My son and I had a terrific experience with Captain Brad. I would highly recommend this school.

Really enjoyed the 101 and 103 class with Captain Brad. He helped us work around some challenging winds to successfully complete the 103 class. Thank you Brad!!!

My wife and I took the ASA 101 class from Capt. Brad and had a great time. We also learned a ton! Capt. Brad did a great job communicating from booking through class completion. We were scheduled to begin sailing 2 days after Hurricane Milton was scheduled to make landfall, meaning we were concerned about sailing, traveling to and from Key West, etc. Milton ended up landing in Tampa and Key West was largely unaffected, but Brad answered our questions and kept us informed in the days leading up to the trip.

The class and boat were both great. The boat was in great shape and the electric motor was an unexpected treat. No noise! The boat seems to be a good size to learn on and Capt Brad did a great job explaining, and then re-explaining things to these 2 land lovers. I, and just as importantly, my wife, never felt rushed, talked down to, or impatience from Brad. He was patient and talked through things so we could both understand.

He was also flexible with our sailing dates when the forecast turned sour. He accommodated our schedule on Friday and Sunday when the weather on Saturday looked bad.

I highly recommend Southernmost Sailing School if you're looking for a great sailing experience in a great location!

Captain Brad was fantastic in preparing me to successfully pass my ASA 101 certification. His extensive sailing knowledge, combined with his calm and patient teaching style, made learning enjoyable and effective for a beginner like me. I'm already looking forward to returning for the next set of courses—can't wait to continue the journey!

Captain Brad was the perfect instructor to get me back in the groove of sailing and hone up my skills. He did not give up with the negative weather forecast, and we were able to go in a 2 day sailing experience that was extraordinary. Besides helping me to improve sailing skills and mooring, he was a great host, cooking dinner, and enjoying a great after meal conversation, and practicing knots 🙂
In the way back we have an encounter with the dolphins that was just amazing. I highly recommend Captain Brad and his Southernmost Sailing School!

Captain Brad made this sailing experience a perfect training to improve my skills and knowledge. Captain Brad is personable, relatable and also focus on safety considering the weather end of August in Key West is unpredictable and with frequent storms. Other sailing companies would have canceled, however he waited until same day to have most updated weather information and we were able to not only go out and mooring one night in a near by Key, we also had a fantastic time: he prepared a great dinner, and we were able to go snorkeling and sailing with the dolphins!
I highly recommend his sailing school.

I agree with all the wonderful things others have said about Captain Brad and the Southernmost Sailing School. I would just like to add that as a single woman taking a sailing class on my own, I was a little nervous about how it would go, but Captain Brad made me feel comfortable immediately and through his support, enabled me to learn the skills necessary to complete ASA 103. I greatly appreciated his expertise and his ability to share it in a friendly and encouraging manner. And because of him, I will be the first to volunteer to haul the anchor aboard. Thank you, Captain Brad.

My brother and I finally began our new sailing adventure with Captain Brad at the Southern Most Sailing School. Key West is a beautiful and challenging place to learn and enjoy. Captain Brad tailored the sailing lessons to the weather and continually challenge us all week. He shared with us many sailing experiences and his experience shows in his sailing and teaching. He was able to very easily navigate us through a few unexpected challenges teaching skills not found in the books. My brother and I left Key West with the confidence and skills needed to plan, prepare, and enjoy coastal sailing with family and friends. Thank you Captain Brad!

Captain Brad was very hospitable and a fantastic teacher. He was patient and and truly cares about making sure you get the value of out of your investment. Key west was the ideal place to learn in a challenging environment. Can’t wait to go use the newly acquired skill with my crew.

We recently had the pleasure of Captain Brad taking me through my ASA 101 class, and doing a refresher of that class for my spouse. I strongly recommend Captain Brad and Southernmost Sailing School for a fun, helpful, and thorough learning experience. He did a wonderful job adjusting to our different skill and comfort levels, and I really appreciate his encouraging approach. His calm reassurance and trust in me helped me to try again...and again...until I had the skills down. You will definitely feel competent and experienced in 101 content by the time you are done, and have a great time doing it. The Sunset Marina was great, and Key West is an awesome location in which to learn. (One tip is to plan on taking a car share to the marina, as parking is not guaranteed). Thanks again for your help, Captain Brad and Sherry!