Learn To Sail in Just 2 Days
(without prior experience)
Southernmost Sailing School gives you an interactive, on-the-water learning experience designed to build real confidence at the helm—so you can start your sailing journey and create the ocean-adventure life you’ve been dreaming of.
Southernmost Sailing School is your step-by-step, how-to guide to becoming a capable, confident sailor.
Taught by Brad Lockwood, these live, interactive, in-person American Sailing Associations (ASA) course/s are an easygoing, fully interactive sailing experience into every component of learning to sail — giving you the tools, skills, and CONFIDENCE you need to start your adventure on the water and live the sea life you’ve been dreaming about.
FIVE STAR REVIEWS
Not Sure If Southernmost Sailing School Is The Right Fit? Let’s Help You Find Out…
✔️ You’ve been dreaming of learning to sail in Key West and want hands-on sailing lessons that teach you how to confidently handle a boat—not just classroom theory.
✔️ You’re searching for a professional ASA sailing school where you can earn your ASA 101, 103, 104, 118, or 111 certifications with expert, beginner-friendly instruction.
✔️ You want to learn from an experienced ASA instructor who makes sailing safe, approachable, and fun while teaching real skills used on the water every day.
✔️ You’re looking for beginner sailing courses or keelboat lessons that give you clear, step-by-step training to become a capable and confident new sailor.
✔️ You want a relaxed Key West learning environment combined with accredited ASA training so you can build the skills to charter, cruise, or skipper your own sailboat.
Feeling that surge of excitement and thinking, “Aye, that’s me”? Then you’re right where you’re meant to be.
Southernmost Sailing offers the following American Sailing Association (ASA) courses to start your sailing adventure…
-
ASA Keelboat 101 — Your Sailing Foundation
Start your journey with essential sailing skills, safe boat handling, and core seamanship—including knot-tying—all taught in a calm, welcoming environment.
-
ASA Coastal Cruising 103 — Expanding Your Capabilities
Build on your 101 experience as you learn to manage a cruising sailboat, refine your navigation, and gain the confidence to explore new waters.
-
ASA Bareboat Cruising 104 — Becoming Skipper-Ready
Step into the role of skipper with real-world training in anchoring, systems management, trip planning, and the skills needed to charter your own cruising sailboat.
-
ASA 118 Docking Endorsement — Dock Like a Pro
Practice smooth, controlled docking through focused hands-on sessions designed to make close-quarters maneuvering feel natural and repeatable.
-
ASA 111 Refresher — A Confident Return to the Water
Perfect for returning sailors—this course brings your skills back up to speed so you can move forward with clarity and confidence.
-
***Save More When You Learn More***
Combine any of our ASA courses and unlock an exclusive package discount!
When you book multiple classes together, you not only fast-track your sailing skills—you also save on tuition. It’s the perfect way to move from beginner to confident skipper while keeping more wind in your wallet.
SPACE IS LIMITED. SECURE YOUR SPOT TODAY! +1.305.407.4141
SPACE IS LIMITED. SECURE YOUR SPOT TODAY! +1.305.407.4141
Just wrapped up an amazing sailing class with my husband and we loved the experience! Captain Brad was absolutely fantastic - super kind, patient, and made sure we grasped every bit of the course material. We felt so comfortable asking questions and learning at our own pace. By the end of the class, we were both confident with the course content. If you're looking for a sailing class that's both fun and informative, look no further. Highly recommend!”
Laura, 101 ASA Graduate
ASA 101: Keel BOAT
$1,200
*per student
Are you ready to join Southernmost Sailing School and become a CONFIDENT sailor?! Review your course options (pun intended) below…
ASA 103: Coastal Cruising
$1,250
*per student
ASA 118: Docking Endoresment
$900
*per student - per day
ASA 104: BareBoat Cruising
$2,400
*includes two students
ASA 111: Refresher
$135/hr
*minimum 4 hours billed
Bring a Friend
$500
*Pay an additional $500 ONLY per friend, per course!
Promo
Learn More Save more
$200 OFF
*$200 discount when you book two or more courses at the time of booking
BEST
VALUE
CALL 305.407.4141 to schedule your class TODAY!
〰️
CALL 305.407.4141 to schedule your class TODAY! 〰️
What Southernmost Sailing Students Are Saying…
-
Jeff
“Southernmost Sailing School is a great! My wife and I did the ASA 104 class with Captain Brad and could not have been happier with the experience. He is a thorough, generous, and patient teacher and makes everything practical and fun. He simplifies things for any level of student. We can't wait to get back to take advantage of more options for sailing. After learning from Captain Brad, you'll feel ready and prepared to begin cruising!”
-
Jason
“Sailing with Captain Brad was beyond expectations and a totally immersive experience! My brother and I have been talking about sailing for years. We are so happy we found Captain Brad to start our journey. He was fun, entertaining, and experienced. Capt. Brad is an exceptional teacher! We learned how to sail safely and with skill. He simplified sailing, made new concepts understandable, and we sailed A LOT! We did a whole week 101/103/104, slept on the boat, and our overnight was to Boca Grande! We are hooked! My brother and I already have plans to return with our families and begin more adventures!”
-
Heather
“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!” -
Sarah
“Sailing with Captain Brad was a real pleasure. We had plenty of one on one time aboard the sailboat and were able to go through so many different sailing scenarios. We were well prepared for our book exams as well as our on the water practicals. Would highly recommend Southernmost Sailing School for your ASA certification courses.”
-
Ed
“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!”
-
Jacob
“My dad and I can’t wait to come back and sail again with Captain Brad. He was the perfect instructor and guide, with endless knowledge and experience to share. We learned so much, through hands on training and repetitive practice. I can’t speak highly enough of this sailing school and Captain Brad’s teaching style. I’ve been recommending to my west coast friends to fly to Florida just to learn from the best.”
ASA 101: Basic Keelboat Sailing Course
Your First Step Into Sailing
This beginner sailing class teaches you the core skills required for your ASA 101 certification. Get comfortable at the helm as you learn the essentials — sail trim, points of sail, basic knots, commands, buoyage, and boating safety — all aboard our 30′ Catalina in calm Key West waters. You’ll practice steering, tacking, and jibing until it feels natural, supported by clear, patient coaching.
***Includes ASA textbook, written exam, hands-on evaluation, and full preparation to pass your ASA 101 certification with confidence.
Dive Deeper Into What You’ll Learn in Each ASA Course…
ASA 103: Coastal Cruising Course
Build Real Cruising Confidence
In this course, you’ll step into true cruising-level sailing. Learn reefing, anchoring, docking, crew coordination, coastal weather awareness, and how to safely operate a larger cruising sailboat. You’ll also get hands-on training with engines and onboard systems — everything you need for safe coastal cruising.
***Includes textbook, written exam, skills evaluation, and coaching to help you earn your ASA 103 Coastal Cruising certification.
ASA 104: Bareboat Cruising COurse
Become Charter Ready
This advanced ASA sailing course teaches you how to skipper a cruising sailboat on multi-day voyages. Learn everything you need to confidently charter a sailboat anywhere in the world. You’ll master anchoring, navigation, cruise planning, and managing all boat systems — plus the real skills you need for safe multi-day cruising.
***Includes ASA textbook, written exam, skills test, and personalized coaching to earn your ASA 104 certification.
Asa 118: Docking Endorsement Course
Master Docking With Confidence
Learn the maneuvering, throttle control, and line-handling skills needed to dock smoothly and safely — even in wind or tight spaces.
***Includes all ASA materials and skills evaluation for your 118 endorsement.
ASA 111: Sailing refresher Course
A Confident Return to The Waters
This refresher course is designed for sailors who want to rebuild skills, regain confidence, or prepare for advanced ASA courses. Your instructor will assess your current skill level and tailor the session so you walk away feeling confident, capable, and ready for your next ASA course or charter.
***Includes ASA materials and hands-on skills review.
It’s everything you need to start sailing with CONFIDENCE!
You won’t just learn what to do — we break it all down for you.
At Southernmost Sailing School, we make learning simple, relaxed, and fun — Key West style.
You’ll get the official ASA student workbook packed with detailed lessons, diagrams, and practice tests, plus our plug & play checklists to help you know exactly what to do the moment you step aboard.
And because sailing is something you learn by doing, you’ll also get hands-on training with an experienced instructor and the support you need to pass your ASA certification with confidence.
Meet Your CAptain
Hi! I’m Brad — Captain, sailor, veteran, and ocean adventurer — and I’m lucky to have my First Mate Sherri and our pup Spice by my side wherever the wind takes us.
I started Southernmost Sailing School in 2014 because sailing didn’t just become a hobby for me — it became a lifeline, a purpose, and the way Sherri (my wife and First Mate) and I built the life we love aboard our own boat.
I’ve had the honor of teaching more than 1,000 sailors since then, and every single review means something to me — especially the fact that they’ve all been 5-stars. At 70 years young, I still put my whole heart into every lesson, every student, and every moment on the water. I want people to feel safe, confident, and welcome the second they step aboard.
I also keep my prices lower than other sailing schools on purpose. When I started dreaming about this life, I didn’t have much. Money was tight, and the world of sailing felt out of reach. I promised myself that if I ever taught others, I’d make sure cost wasn’t the thing that held someone back from living their sailing dream.
Here, you’ll get patient, personal, hands-on training — the kind that comes from a lifetime on the water — without the barrier of high prices. My goal is simple: to share the joy and freedom sailing has given me, and help you feel it for yourself.
“We sail not to escape life but for life not to escape us.”
~Let’s sail
CALL. TEXT. CONNECT. 305.407.4141
Honoring Those Who Served: Veterans Sail FREE!
As a veteran himself, Captain Brad knows firsthand the value of community, purpose, and time spent on the water. Sailing played a powerful role in his own journey, and it’s something he believes every veteran deserves the chance to experience.
Every second weekend of the month, Captain Brad opens the doors of Southernmost Sailing School to fellow veterans and offers free learn-to-sail training—no catch, just gratitude and giving back. This is real, hands-on sailing instruction in the beautiful waters of Key West, taught with patience, respect, and camaraderie.
Spots are very limited and fill quickly. If you’re a veteran interested in learning to sail—or if you know a veteran who would love this opportunity—we encourage you to sign up as soon as possible and help spread the word. 🌊⚓️
Conditions Apply:
Courses are offered November through May, on the second weekend of each month. Enrollment is limited to four veterans per weekend.
Participants must provide proof of veteran status.
Participants must be able-bodied seamen.
Veteran students are responsible for all personal expenses, including travel to and from Key West and course materials.
Course materials cost approximately $150 and include study books, online course access, exams, and ASA certification. Payment is due at the time of booking, and all reservations must be made at least 30 days prior to the start of the class.
“If you’re excited to start sailing, I’m here to share everything I’ve learned from my 30+ years on the water—so you can grow your skills quickly and confidently, relax, and truly enjoy the sailing life.” - Captain Brad
-
If you’re brand new to sailing, you’ll start with ASA 101. Already have some time at the helm? You can jump into ASA 103 or 104 after a quick skills check. We’re happy to help you choose the right starting point.
-
You’ll get a simple, step-by-step Study Roadmap that walks you through exactly what to do before your hands-on training. Most students spend 6-8 hours per course reviewing the ASA student manual, completing the practice tests, and getting familiar with the skills and terminology.
This light prep work makes your time on the water much easier—and ensures you show up confident, ready to learn, and able to make the most of every minute at the helm.
-
You’ll get the ASA Student Workbook, detailed lessons, practice tests, on-the-water training, safety instruction, and hands-on coaching from an experienced instructor—all taught in the calm, warm waters of Key West.
-
We keep classes small and personal—usually just 2–4 students—so you get plenty of helm time and one-on-one support.
-
Nope! Beginners are absolutely welcome and encouraged to join us. We teach from the ground up in a relaxed, friendly environment—no pressure, no yelling, just learning and enjoying the water.
-
Yes! ASA certifications are accepted worldwide and are the gold standard for bareboat charters and skill progression.
-
Sunscreen, a hat, water bottle, lunch/snacks, and non-marking shoes are all you need — along with a willing spirit. All training materials and sailing gear are provided.
-
Safety first. If conditions aren’t suitable, we’ll reschedule or adjust the lesson plan. Luckily, Key West gives us great sailing weather most days of the year.
-
Absolutely! Many students love learning with a friend. If your friend also wants to take the course, you’ll both receive a special enrollment discount when you sign up together.
If they’re not taking the course, they’re still welcome to hang out and relax at the marina—but they can’t join the on-the-water training unless they’re officially enrolled.
-
Yes! With the combination of hands-on instruction, skill assessments, and real helm time, most students feel confident handling a sailboat on their own after completing the 101–104 series.
-
When it comes to the common concerns about age, weight, and height for private jet flight attendants:
Age: While age is just a number, most jobs require you to be at least 21, mainly to legally purchase alcohol for flights.
Weight: Your ability to move quickly in emergencies and navigate through the smaller exits of private jets is crucial. This means your weight and size should not hinder your ability to ensure the safety of everyone on board.
Height: Considering the average interior height of private jets is around 6 feet, being taller might require additional consideration for comfort and mobility inside the cabin.
