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Southern Most Sailing LLC
Average rating:  
 86 reviews
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!

by Mike on Southern Most Sailing LLC
Capt. Brad and Last Call

I'm 59 and my son is 31. We finished our 101 class with Capt. Brad and loved it. We learned a ton. Great balance of bookwork and time on the water. Capt Brad was both patient and effective in his instruction. Staying on his boat for three nights was an added plus. We were also able to snorkel a bit and enjoy the evenings in Key West.
Looking forward to getting experience on the water and make it back to take the 103 and 104 classes in the near future!

by Bart Leonard on Southern Most Sailing LLC
Better than expected

My wife and I took the ASA 101,103,and 104 classes with Captain
Brad in December. It was amazing. The sailing was great, The water was beautiful and Captain Brad was fantastic. I would reccomend Southernmost Sailing School to anyone interested in sailing. We can't wait to go back!!!

by Donnie Beckmann on Southern Most Sailing LLC
3 Day Charter

In November of 2017, I took the ASA 103 and 104 courses with Captain Brad. I had such a good time sailing with him, that when I decided to sail again in November of 2018 he was the only call I made.
On the first day we sailed to Cottrell Key to get some snorkeling in. Brad knew exactly where we needed to be to get in the best snorkeling, we even got to see some dolphins on the way out.
The second day we sailed over to watch one of the powerboat races and ended up watching all three. After the races were over we got back to sailing and threw a couple fishing lines out to see if we could catch supper. We struck out with the fish, but there was a great sunset to watch as we sailed back to the marina.
After having two great days on the water Captain Brad had somehow saved the best for last. We threw the fishing lines back in the water as we sailed to Archer Key. We caught one small fish, threw it back after some thought about it becoming bait, but at least we weren't skunked again. Brad knew exactly where to find the sponges by Archer Key so that we could try to catch some lobsters. He gave me a lot of advice and had all the equipment to catch lobsters, but I wasn't able to catch any. On the way back to the marina we stopped by a shipwreck got in some more snorkeling.
Brad and Sherri are great people, easygoing and fun to talk to. They will do anything they can to make your trip to Key West more enjoyable and always seem happy to help. I'm glad I found their school and will absolutely be using them again.

by D DeLoach on Southern Most Sailing LLC
Fantastic experience!

My wife and I took the 2-day ASA 101 course with Brad, then added an extra day to practice and have some more fun. The training was excellent, and we really enjoyed the extra day with no "exam pressure" and some more interesting, gusty winds that gave us extra learning beyond what we had seen in the course to that point. I highly recommend adding an extra day if you have it in your itinerary.

We also stayed on the boat all 3 nights and had fun with it. Lots of great food in the vicinity, everything walkable so no car needed, and the marina has a nice bathroom/shower setup.

We had very little boat experience but Brad is very patient teacher, as well as just being a great guy! Sherri was also excellent at handling the various trip details and getting us the study materials in time, even starting us a day early to avoid some potential weather issues.

I chose Southernmost Sailing over other Key West options because I got the feeling it was a more intimate experience, not a corporate type of school, and that is definitely the case. Also, I think Key West is a particularly good area for sailing training, with warm mostly shallow water (so no wet suits needed and no huge waves to deal with) and good wind and weather year-round.

Really, you just can't go wrong with choosing Brad as your instructor. Nice boats, nice folks, nice place, nice waters (and nice dogs too)!

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