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Southern Most Sailing LLC
Average rating:  
 138 reviews
 by Marla
Incredible Learning Experience

I had the privilege of taking the ASA 103 course with Captain Brad. It was phenomenal! Captain Brad is an excellent instructor. He is very patient as well and at the same time quite laid back and very easy to talk to. No question is a dumb question. He also has a gift for teaching this art, as I will call it. Sailing is all very new to me and he is definitely the kind of instructor a newbie like me needs. One awesome bonus is that the sailboat used for the class has an electric engine— so no noise and no smelly fuel. We had the most perfect weather and three fantastic days of sailing on the most beautiful water. I can’t wait to go back!!

 by Megan Milam
Amazing Sailing!

My friend and I took our 103 class with Brad after completing our 101 on a lake with little wind. It was a big step up for us, but Capt Brad was patient and kept calm while instructing and answering all our questions! We really enjoyed learning with him and got a lot more comfortable on the water. Sailing is hard work, but also a lot of fun!

 by Francisco
Learn to Sail in Paradise

My wife and I had the pleasure of taking the ASA 103 course with Captain Brad. We both came out of the experience having gained the knowledge, skills, and confidence to continue our sailing journey. Captain Brad is a great teacher and a savvy sailor. He provides clear instruction with ample patience and a dash of good humor. He embodies the way sailing should be: precise and fun.
During our two-days course, we also got to experience some of the treasures that Key West can offer: We were able to snorkel and explore a century-old shipwreck and sail alongside a group of eight very curious bottlenose dolphins.
If you are looking to learn something new or hone your existing skills - Look no further!

 by Angela
Superior Sailing School

When trying to decide which sailing school was right for us, the great website descriptions and Facebook videos convinced us to choose Southernmost Sailing School. This was absolutely the best choice. We enjoyed the entire experience.

 by Chris Roberts
Life Changing Experience!




I took Captain Brad's ASA 101 and 103 courses. It was my first time sailing a big boat, and I was nervous, but Brad's demeanor put me at ease.As a retired teacher, I can say with confidence what good teaching looks like. Brad is a great teacher because of his patience, positivity, organization, and dedication. He really cares about his students, and he has the experience to go with it! I have plans to return next year and take ASA 104. I would 100% recommend Southernmost Sailing School to my friends and family!

 by Lo
Great experience!

Free My friend and I just took ASA 101 and 103 from Captain Brad and we had a great experience! He was incredibly patient, nice, and knowledgeable. We felt very comfortable the entire time and our stay on the boat was fantastic. We both plan to take further classes through him in the future!

 by Claire Roberts
Southernmost Sailing

My mom and I took the ASA 101 and 103 course with Captain Brad at the southernmost sailing school over 4 days. Truly an amazing and unforgettable experience. Brad is a great teacher; extremely knowledgeable, patient, and passionate about sailing. I can guarantee you will leave this school with confidence to sail on your own and a love for sailing yourself. Not to mention, the location rocks. We can’t wait to take more classes from Captain Brad. Thank you southernmost sailing school! Book yours now, you won’t regret it!

 by David and Elizabeth G
Sailing 101 March 2022

Thank you Brad for an amazing Experience and all your knowledge in instructing us for our ASA 101 course. It was a wonderful time and your knowledge and passion of sailing is inspiring. Highly recommend!

 by Chris Benton
Awesome Course

This is not your relaxing, beer drinking course that you would think it would be. We took ASA 101 and 103 over 4 days. It required a lot of studying and sailing. We learned a lot and got pretty comfortable with the boat. Captain Brad is a standup guy who is easy to talk to. I am definitely glad that I took the course through him. I am looking forward to taking 104 with him in the future. If you want to learn to sail, this is your course. Thanks again Captain Brad!

 by Matthew Wiedrick
ASA 101, 103 and 104

Fantastic sailing and learning experience with Southernmost Sailing School aboard SV Obsession!
My wife and I completed ASA 101, 103, and 104 with Captain Brad. We had a great time and learned so much more than we thought we would. If you are looking for a sailing school, look no further, sign up now with Southernmost Sailing School...you won't regret it!

 by Daniel Sheps
Excellent course from a very experienced and fun captain

Captain Lockwood is a great skipper. We took ASA 101 and ASA 103 with the intention of getting some hours logged to eventually bareboat our own monohaul or sailing cat around the Caribbean.

All of the information from Captain Brad was high yield. His average score on the 100 question written test is 93% and he has instructed over 700 students!

The sailboat was in great working order and we were thrilled to have time to anchor and snorkel at a shipwreck.

An added bonus Captain Lockwood will soon be installing an electric motor and selling the 25 hp diesel engine.

Captain Lockwood is especially skilled at teaching how to plot a course with charts and compass. His old school method gives us solace when the GPS is unable to capture a signal due to clouds or malfunction.

I felt very confident navigating a full size sailboat after performing his quick stop/ man overboard drill several times. The key west harbor is busy with jet skis, multiple boats out at anchor, and day trip traffic however I was sure of my ability to navigate, tack, and jibe- the instruction area is actually a perfect harbor with crystal clear water.

I would highly recommend this instructor.

 by Barbara Ardell
Great Learning & Sailing Adventure

My grown daughter and I sailed with Captain Brad for 2 1/2 days celebrating our milestone birthdays. My daughter got her ASA 101 Certification and I had a great time sailing along. Brad went above and beyond and even fixed us an excellent breakfast and dinner. My daughter learned way more than a typical 101 class. We had a great time. Brad is friendly, knowledgable, professional and lots of fun!

 by Mark
Great Trip!

Thanks to Capt Brad for a great time and learning experience during our ASA104 course. He was extremely informative and patient as we learned the ropes of the coursework and skills. We had a great trip on the Catalina 30 and a wonderful dinner of fish, red beans and rice. What a memorable and educational trip. Thanks for all of your help Capt Brad in getting us one step closer to our dreams!

 by Christine
Highly Recommend!

We had an outstanding experience taking the ASA 103 Class with Captain Brad. You will not find a more knowledge, experienced, or safe instructor. We are looking forward to taking the ASA 104 with him.

 by Katy Corrigan
ASA 101,103 and105

My husband and I signed up for Captain Brad's ASA course after starting to crew on a racing team in Cleveland Ohio. Wow, what a terrific experience. We were out on the water practicing skills everyday and studying at night. From the reservations to the final goodbye I could not have asked for a better week. Since we are so new to sailing I don't think we'll be Captaining vessel soon but our new knowledge of sailing has given us a taste of the lifestyle and craft. Captain Mike was our instructor. He was terrific, informative, fun and didn't let us land lubbers get away easy!! So thankful for the experience.

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