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!

My husband and I bought a MacGregor motor/sailor with the idea of motoring through the Great Loop. Wanting to spend time living aboard before we took off, we booked a month at a Keys marina. While researching marinas, we found one with Brad's Southernmost Sailing school. Bingo! We could learn to live aboard AND learn to sail. We were lucky to be able to book the dates we wanted and went through 101 and 103. What a learning curve! Brad couldn't have been a better teacher. Not only is he incredibly knowledgeable, he's also patient, kind and great at letting you give it a go on your own with correction before things get dangerous. We have so much more confidence now to get sailing on our boat. We wouldn't be able to say that without the instruction from Captain Brad. We also need to acknowledge Brad's wife Sherri. She answered our questions about booking, got us our class materials quickly and was also so easy and kind to deal with. What a great team!

Captain Brad was the best teacher I could have hoped for. He's such a great guy all around.

Lived on the boat for almost a week and took the ASA 103 & 104 classes. Best way to spend your time getting the feel for liveaboard cruising.
I fell in love with sailing as a passenger years back and was finally in the position to take the role of skipper.
Key West was an ideal location to learn. The area is sure to test your skill but at the same time makes you feel comfortable and at home.
I can't imagine finding a better teacher or location than Captain Brad in Key West!