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Southern Most Sailing LLC
Average rating:  
 90 reviews
by Paula & Darrin on Southern Most Sailing LLC
Fun Times Sailing in The Keys

My husband and I took 101, 103, and 104 sailing classes with Capt. Brad and first mate Sherry. My husband had sailed years ago, and while I had been on sailboats, I had never officially sailed. They not only made the sailing fun, but went out of their way to pick us up every morning, and drop us off back at The Perry hotel (which we loved and highly recommend). Brad's laid back approach was perfect, yet he didn't miss a thing on instruction and pertinent points in learning. We plan on going back to sail around The Keys on the 26' Hunter "Last Call", and surrounding area to perfect all of what Brad taught us. Definitely recommend Southern Most Sailing School for fun while getting not only excellent instruction, but also amazing hospitality with Brad and Sherry.

by Jim Condes on Southern Most Sailing LLC
Great sailing instruction

My wife and I took 101, 103 and 104 with Captain Brad. We both had sailed before, but it was a long time ago. Captain Brad started each morning with lessons from the book after which we would go sailing and practice what we had talked about in the morning. His teaching was methodical and his instructions easy to understand. He also gave us a very thorough understanding of navigating around Key West and around the Keys. We enjoy our sailing skills a lot and will definitely use Southern Most Sailing school for any other sailing courses we want to take in the future.

by Mark M on Southern Most Sailing LLC
Great Refresher!

I have 101, 103 and 104 certification but had not been sailing for 4 years. So, when a trip to the Keys was coming up and great sailing weather, it was time for a refresher course. Brad offered the ASA refresher course. We had a great day on the water with a fun boat. Brad was the best instructor we’ve had with the ability to explain techniques in a straightforward manner. And rather than just say “that’s just the way you do it”, as past instructors have, he gave great explanations as to the why. I learned a lot and will certainly look for another lesson with Brad the next time I’m in the Keys.

by Craig Perkins on Southern Most Sailing LLC
good ASA 104 class

My wife and I took our 104 class recently with Captain Brad and can definitely recommend his sailing school. His teaching is low key but effective, and we both passed the 104 exam without trouble. One thing that we particularly liked was how Captain Brad tailored the lessons to our previous experiences as well as what we were looking for in a 104 class. We enjoyed his numerous sailing anecdotes, all of which were instructive in some way or another. Finally, we were impressed with his humanity: after our class was over and we were on our way back to the marina, we passed a small sloop at anchor that had onboard two large dogs who appeared to be alone and in trouble. Captain Brad did not hesitate to swing the Phoenix around and check on the dogs. After ascertaining that the dogs were indeed abandoned without food or water, we stayed on site until authorities and neighboring sailors rescued the dogs. I'm not sure how many other captains would have acted on the slim chance that the dogs were really in trouble, but they were and we firmly believe that two beautiful dogs are alive today because of Captain Brad. Thanks again Captain Brad and First Mate Sherri for a memorable ASA 104 experience!

by Melissa R on Southern Most Sailing LLC
Fantastic experience

Captain Brad is knowledgeable, patient and fun, everything you want in an instructor. Took the ASA 101 course, and his instruction was great, excellent direction without being overwhelming. His 26’ sloop was perfect for sailing and maneuvering around Key West. He also prepared us very well for the exam. I highly recommend Captain Brad for all your sailing instruction.

by Mandy Friend on Southern Most Sailing LLC
I'm so glad I let my husband talk me into it!

I had the time of my life going through ASA 101 aka "sailing boot camp" with Captain Brad! My husband originally booked the lessons alone because he just knew there was no way I would agree to do it with him, but, alas, I agreed to go and he booked it for the both of us. It was the best decision ever! I had had ZERO experience with sailing having grown up only on motorboats. Let me tell you, there is just something about cruising the ocean in a sailboat that a motorboat can NEVER give you. I am hooked! We are planning for ASA 103 soon! There is much to learn when learning to sail, but THANK YOU, Captain Brad, for making learning it so much fun! And I have to put on the record that, in fact, I got a better score than my husband on our final exam!! LOL!

by Eric and Jen on Southern Most Sailing LLC
The start of a life filled with adventure!

We had an amazing sailing experience with Brad at Southernmost Sailing School in beautiful Key West! We had so much fun that we didn’t realize how much we were learning along the way...he did an excellent job of preparing us for the exam. The 26’ Hunter sailboat was not only great to learn on, we also slept well on it every night and got a taste of what life on a sailboat is all about. We had so many awesome wildlife encounters... a school of dolphins, a sea turtle, rolling Tarpon, and an up close and personal encounter with the resident manatee! Brad was great about making sure that we were able to take pictures and have the best experience possible. Getting to know Brad, Sherri and their two adorable dogs gave us a glimpse of the adventure and satisfaction that living on a sailboat offers. We would recommend the Southernmost Sailing School to anyone interested in making sailing part of their life!

by Paul on Southern Most Sailing LLC

I want to thank Captain Brad, Sherry, Sugar & Spice!

I started sailing with Captain Brad just 6 weeks ago and spent a mere 6 days with him & his crew, and today I passed my ASA104 exam, allowing me to charter around the world. He has opened up a new chapter in my life.

Captain Brad is the ideal teacher - knowledgeable, patient, supportive and has a great sense of humor. His qualities made my quest successful. If you really want to master sailing I can't think of a better teacher / captain.

Thanks a million Brad!


by Jermiah Osborne on Southern Most Sailing LLC
The Rest of Your Life

I'm 31 and not in the best physical shape of my life...but I did it! The whole thing 101,103 and 104. A "green horn" first time on a sailboat, Captain Brad made into a confident Helmsman in no time. Before long we were trolling for the colorful Mahi Mahi. Though we didnt hook our target there were fish a plenty Bonita, spanish macks, a beautiful red grouper an even a little grunt. We moored on the edge of Boca Grande for an overnight stay. With a sunset and rise even a post card couldn't capture. Captain Brad took the time to ensure I was comfortable with all aspects of the "sailing life". I took a wealth of knowledge from the experience and truly believe it will forever chang my course in life. So if your on the fence about taking the course's think of it as more than a certification it's "The Beginning of the Rest of Your Life". Less than 1% of the people you know an will meet in life, will not have this opportunity so reach out and contact Captain Brad or First Mate Sherry. I promise you'll wish you had sooner,then you'll wish you could do it again! A Big Thank You to Mrs. Sherry for your southern hospitality and Gooooood....Cook N. A shout out to Sugar & Spice " love you mean it"!

by Jay Muscatello on Southern Most Sailing LLC
ASA 101 and snorkeling

Thoroughly enjoyed my first formal sailing training under Captain Brad. The winds weren’t always favorable but the experience was not diminished. By the end of the second day I was confident at the helm and both sails. Brad is personable, entertaining and knowledgeable. If you every think you want to learn to sail this is the way to do it!

by Paul on Southern Most Sailing LLC
Highly Recommended Sailing Academy

I took the ASA101 course with Captain Brad this week & it was great! I left after two enjoyable days capable to sail mid-sized monohulls & knowledgable enough to communicate clearly using sailing terminology. I plan to take 103 & 104 with Captain Brad, because I know that he can successfully make me a competent sailor able to charter & eventually own my own boat. Thanks Brad!

by Brandon Rabke on Southern Most Sailing LLC
Successful Trip to Key West

My friends and I had a great time sailing with Brad last January. Though the weather wasn't perfect, Brad was able to find times of the day and areas to sail where we could still complete our instruction. All three of us acquired the knowledge and skills necessary to complete the ASA 101 course. We're already planning our next sailing adventure!

by James Morken on Southern Most Sailing LLC
mission accomplished

My wife and I had a great experience learning to sail with Brad. One big goal of mine was for my wife to feel comfortable being on a sailboat and learning the basics so we can someday have a boat of our own. Mission accomplished she is ready and so am I. Brad you have the patience of Job.

by George Gross on Southern Most Sailing LLC
custom sailboat charter refresher

After a 14 year absence, my wife and I wanted to refresh our bare boat chartering and ASA sailing skills. We worked with Captain Brad to devise a 3 day custom on the water training program. He provided the expertise and coaching we needed to become comfortable and safe when we next take out a chartered sailboat. Most of Key West's waters are very shallow and sailing them is safer when you have aboard someone with local knowledge. We were very impressed with Captain Brad's command of the local waterways and his low-key yet effective teaching style. We highly recommend considering the Southernmost Sailing School for either your ASA training or for a flexible re-entry training to tune up your bare boat charter sailing skills.

by Joe Turney on Southern Most Sailing LLC
Awesome learning adventure

I had an amazing experience with Brad. Thanks to his coaching and teaching I was able to score a 97 on my 101 exam! I'm looking forward to coming back to move on to more advanced topics. I don't think you can find a better school!

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