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Southern Most Sailing LLC
Average rating:  
 119 reviews
by Phil Cooper on Southern Most Sailing LLC
Many Many Thanks Captain Brad

In March my wife Stephanie and I took our 103 and 104 with Captain Brad who was the most patient teacher ever. We recently bareboat chatered out of Mystic, Connecticut. We used our new skills crossing over to Block Island and then back to Stonington and Fishers Island. What an adventure! We have to thank Capt Brad for this,he prepaired us well,We used every single thing he taught us and with his encouragement to get out there . We did! And had the time of our lives,thanks again Capt Brad! You Rock!

by Eric on Southern Most Sailing LLC
Amazing experience!

Had an amazing time in ASA101 & 103 class with Southern Moat Sailing. I did a private class which they catered to my specific needs and spent extra time where I needed it the most. They were flexible with scheduling as a storm delayed class by a couple days. They made sure I had everything completed before I left the keys. I left class a much more confident sailor.

by Ann Laurent on Southern Most Sailing LLC

I knew almost nothing about sailing, except that I loved the concept that one can partner with the wind to travel across an expanse of water. On a whim, I thought I'd try some lessons while in Key West, just to get my feet wet to see if I liked it.
My expectations were minimal. Just a little taste of what sailing was like was all that I thought I would experience in a 2 day course. My expectations were greatly exceeded! Captain Brad jumped right in with clear course work, and hands-on, instruction. His patience and enthusiasm made it all the more enjoyable. By the end of the second day, I felt totally confident in my ability to not only be a deck hand or helmsman, but also, to lead the process (on a micro-level) myself.:)The sense of empowerment and wonder in learning all the new terminology and concepts of sailing, while being able to master them in practice was nothing short of exhilarating! A whole new world has opened! I highly recommend Captain Brad at Southernmost Sailing School!

by Teresa Krijger on Southern Most Sailing LLC
Many thanks

My son and I were fortunate enough to get a last minute booking for the 101 and 103 course at the end of July with Captain Brad. Unfortunately due to flight cancellations , we missed the first day of sailing and were only able to complete the 101. Despite this and a lot of windless weather, we thoroughly enjoyed the experience. Brad was patient (answered our thousand questions) and clear in his instruction and made the best of the difficult weather for us. He was kind enough to fetch us from the airport and drive us back to our hotel which was miles away. I can highly recommend Captain Brad and this experience. Many thanks and much appreciation!

by Fero Kovac on Southern Most Sailing LLC
Thank you for the great introduction to sailing

My wife and I just returned from the trip to the Florida Keys with the primary goal to learn how to sail. Captain's Brad wife Sherri made it easy to sign up for the ASA 101 course. A few days later, I received the "Sailing made easy" book, simple instructions (do not forget the sailing gloves. On the second day, my wife forget hers in the hotel, and Brad had a spare luckily), and the piece of marine rope to practice the knots.
The course by far exceeded our expectations. We thought we would like sailing for sure, but instead, we fell in love with it. It was challenging at first, but Brad did such a great job letting us patiently figure it out until it clicked. Before we returned home to Ohio, we booked another day of sailing with Southernmost Sailing School a few weeks from now, and ASA 103 and 104 are the next step. Thank you for opening a new horizon for us.

by Martha Mainiero on Southern Most Sailing LLC
Wise teacher

Captain Brad is a great sailor and outstanding teacher. We took the 103 course, and were very pleased with how much we learned while also having a very enjoyable 2 days! He took time to understand our level of knowledge and tailored his instruction to make sure we spent the most time practicing those drills we needed most. He is not just going through the motions or teaching to the book but is making good sailors. I highly recommend his instruction for either basic or advanced sailors. He has some amazing sailing yarns to tell! Thanks Captain!

by Amy & Trevor Buhler on Southern Most Sailing LLC
Top notch

My husband and I had previously taken ASA 101, 103, and 104 courses and a year later purchased our sailboat. Captain Brad came and gave us personalized instruction on our boat. It was extremely valuable and helpful knowledge as he assisted with setting up the most optimal sail plan for our sailboat, helped rig reefing lines, assisted with docking maneuvers and helped us understand the capabilities of our new home. We are extremely grateful and highly recommend this service. He was able to drive to our location, give instruction and instill the confidence in us that we needed to begin our new adventure on SV Beyond! Thank you!

by Pamela Macatee on Southern Most Sailing LLC
Patience was a Virtue

As my husband is an experienced sailor and we just took possession of our own Beneteau 38, I am over-the-top grateful that he encouraged me to take the ASA 101 course and become a safe and able 'first mate'!! This course, believe it or not, was my actual first time on a monohull...all my sailing experience was on chartered catamarans. Needless to say, my brain was overstuffed with new information and the processes of actual sailing, and I repeat that patience is certainly a virtue and a virtue I am glad Captain Brad possesses! When he finally said, 'you did it, we've covered all the practice drills' I was relieved, elated and a great happy-tired! Our trip home from beautiful Key West was a celebratory experience, to be sure...
So, moral to the story: even if you have zero experience, you can do this! We are thrilled to have our boat and cannot wait to begin our own adventures! Thank you, Captain Brad, for your knowledge, for your great stories, and for your tenacity as a teacher!

by Jason W on Southern Most Sailing LLC
Fantastic experience

What a great time! Came down to do 103 and 104 and am so glad I did. I wanted to, generally, broaden my sailing knowledge but, having just bought my very first sailboat, I had very specific things i wanted to get from the class to apply to my own boat. Outside of showing me practical applications of the lesson plan, Brad actually went over the specifications of my boat with me and showed me how systems and equipment in my boat would work.

Beyong that, Brad was just a lot of fun to go sailing with. I couldn't recommend this school any more highly.

by Phil and Stephanie Cooper on Southern Most Sailing LLC
Awesome Time !!!!!

Captain Brad is Awesome, everything was perfect! Our experience far exceded our expectations! Accommodations on the Hunter 26 was clean and very comfortable, staying in the marina in the middle of paradise.....it doesnt get any better! Capt Brad was very easy-going and patient with us. Very knowledgeable and forthcoming with information.
Our overnight 104 course was great,we sailed down to Boca Grande where we
Watched a most beautiful sunset,ate an amazing dinner prepaired by our Capt. Mahi Mahi with red beans and rice! Afterwards we had cocktails and played dice game while swapping stories. Overall it was incredable. We walked away having learned so much,feeling confident about our dreams to sail off into the sunset!

The recommendations for the best local cuisine were perfect too!

by Mario Calvo on Southern Most Sailing LLC
ASA 103 - March 2021

Had the opportunity to work with Captain Brad & his first mate (wife) Shari to do a refresher on ASA 101 & get my ASA 103 certification in March 2021. First of all, Shari was awesome to work with to coordinate dates & logistics for the trip. Always responsive, helpful & very pleasant to work with. Though I didn’t get to meet her in person, I talked to her often before the trip & knew that they ran a top notch operation.

Captain Brad was equally amazing. He’s a great teacher that’s patient, great at explaining & walking through all the material. I walked away feeling not only comfortable & knowledgeable of coastal navigation, but also energized to be able to put what I learned into practice back home. His boat, “The Last Call” is in great shape & you can tell he takes pride in keeping it in great condition. He gives you plenty of hands on experience & little by little let’s you take charge of the helm entirely; but always ready to step in in case there’s a need (we sailed a couple days in high winds & totally needed his expertise). Plus, he’s a great person to hang out with, chat & learn about the history & nuances of sailing.

I’d recommend Southernmost Sailing for sure. Great team, great experience & who can beat Key West!

Thanks again Brad & Shari. Hope to do other courses with you in the future.

by Kevin Fortriede on Southern Most Sailing LLC
A pirate looks at 50

I read upon the dingy wall, the words the old man said, "For a good time in Key West, call Captain Brad at Southernmost Sailing School!".
I tell you, it's never too early to do something you will love but eventually, it will be too late.
Captain Brad might be something of a celebrity on KW since everyone seems to know him. Perhaps because he worked with so many others, learning his trade, then so many have worked with him to learn theirs. The result is a confident & patient American Sailing Association accredited instructor who lives the life he sells upon a sailboat, full time, with his wife Sherri. Together they are kind and patient and display warm hospitality.
Life's short. Call now.

by Bradley on Southern Most Sailing LLC
Dreams made to reality

Captain Brad and Sherri were great at getting everything together and worked out for the dates for the classes and were flexible even when I had to make last minute changes. Extremely professional and Captain Brad knows his stuff! He made learning the amount of information seem not only easy but applicable and was the beginning of a kids dream come true! Had an amazing time and even got to sail with the dolphins and turtles all in 2 days! I highly recommend to anyone that has even the slightest curiosity to be out on the water to have Southernmost sailing take you out there’s so much you learn and experience that I can say it’s hands down one of the things you must do in your life!

by Jackson B Leach on Southern Most Sailing LLC
Best of times

Cant think of a better way to spend two days. Captain Brad was very knowlegable and patient as they come. Any questions we had were answered , in a way to best understand before going forward. Clean boat, great instructor, learned alot in two days. Highly recommended

by Andre Melendez on Southern Most Sailing LLC
Awesome week of Sailing during Covid

My wife and I just completed our ASA 101, 103 and 104 classes with Captain Brad at the Southernmost Sailing School. It was the trip of a life time that had been postponed 3 times due to Covid. Our scheduled flight was delayed and we were starting to get the idea that the trip might not happen. Even with our delay the Captain was there to show us around and get us settled in on the first day on the Last Call. While the accommodations aboard the boat were tight, especially if you have not experienced live aboard a sailboat, it was well worth it to be on the water to watch the fantastic sunrise and sunsets. The marina store has many basic needs and many delivery options nearby for food. The first day of lessons were wonderful and Cap walks you through everything in the book and on the water. My wife was very nervous and felt she could not do it but after the first day and the Captain’s incredible teaching style she was extremely comfortable and eventually managed to pass all her classes with flying colors. I loved taking all three courses back to back as you essentially cemented everything you learned to get you comfortable sailing a larger vessel. The 101 class got you used to all the sailing lingo, followed by the 103 where you became more comfortable with the boat and navigation. The 104 took us on a larger vessel and made us very confident that we could actually run the vessel on our own. The last day of sailing we had set out to beautiful Boca Grande Key but as we headed out toward our destination the weather turned and we settled in to anchor in a nice sheltered bay after practicing our sailing in some hefty winds. Cap cooked up some great mahi mahi with red beans and rice and we spent the evening chatting and learning a new dice game of Crapout. This was a great adventure and learning experience as Captain Brad made sure that safety is the most important part of sailing. It was the experience of a lifetime and I felt after all was done that I had made a great friend and confidant in Captain Brad. We are already scheduling our next adventure and will consult the Captain for guidance. Thank you Cap for everything and making a dream trip come true.

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