ONE OF THE BEST WEEKS of my life so far! I've always been a water person but now have a love for the sea one might only hear about in books or songs. Captain Brad has an excellent understanding of effective teaching methods, an incredible knowledge of sailing and a fantastic way of making his students feel at ease. I feel extremely confident that having taken the ASA 101/103/104 sequence together with him we can now navigate most anywhere we want to go. On our overnight experience he prepared an amazing MahiMahi over red beans and rice we enjoyed while watching a beautiful sunset anchored just off Boca Grande. Even played an original song in his guitar for us. Got us on a real nice Red Snapper that we ate for dinner dockside the last night. Couldn't ask for a better combination of learning, experience and FUN! Thank you #SouthernmostSailing ! read more

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We recently had the pleasure of Captain Brad taking me through my ASA 101 class, and doing a refresher of that class for my spouse. I strongly recommend Captain Brad and Southernmost Sailing School for a fun, helpful, and thorough learning experience. He did a wonderful job adjusting to our different skill and comfort levels, and I really appreciate his encouraging approach. His calm reassurance and trust in me helped me to try again...and again...until I had the skills down. You will definitely feel competent and experienced in 101 content by the time you are done, and have a great time doing it. The Sunset Marina was great, and Key West is an awesome location in which to learn. (One tip is to plan on taking a car share to the marina, as parking is not guaranteed). Thanks again for your help, Captain Brad and Sherry! read more

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! read more

Southernmost Sailing School - Specialty Schools Near Me - Key West, Florida

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. read more

Excellent course and Instructor. I took 101,103, and 104 all together. Good "hands on" training and knowledge. Captain Brad does an excellent job working with students to achieve desired knowledge and goals throughout the course. The manuals are beneficial for knowledge and future reference. Great customer service, knowledge, and enjoyable read more

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. read more

Southernmost Sailing School - Left to right, Me, spice, Captain Brad and sugar. - Specialty Schools Near Me - Key West, Florida

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! read more

My girlfriend and I have discussed taking sailing lessons for years now and only on our most recent trip to Key West October 26-31st 2017 did we finally commit to the idea. We were at first concerned about the recent hurricane damage but to our surprise Key West was great, all businesses were open and most important the Southernmost Sailing School. We had no issues doing all the fun things we like to do and not to mention the weather was beautiful. Capt. Brad was the right Capt for us. Neither myself or GF had much of any sailing experience. We enjoyed the quality instruction and his years of experience were great to have aboard on our 2 day journey. Thanks Capt Brad for making our trip to Key West the most memorable. Sincerely, your two Keelboat students from Missouri. P.S. - stop thinking about taking sailing lessons, just do it! read more

Our family took the ASA 101 Basic Keelboat Certification class in March 2016. There were 6 of us ranging in age from teens through 50's. We had a wonderful time and learned a lot. Our pre-class sailing experience ranged from some-to-none. The coursebook was mailed to us ahead of time. It helped greatly to read through the book and answer the chapter test questions ahead of time. The class was two days. Part of the mornings were spent in class (on the boat), the vast majority of the day was on the water. We split up into 2 groups, working two boats with a captain on each vessel. Capt. Brad was excellent. Especially calm and reassuring to those of us who had never been sailing before and were unsure of themselves. We all passed the certification exam and had a great time. Highly recommended. Would be great for couples and families with teens and above. read more

Southernmost Sailing School - Specialty Schools Near Me - Key West, Florida

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. read more

Wow! Captain Brad and his wife Cheryl are the absolute best. If you are interested in learning to sail do not bother with another school, contact them immediately. We had such a great time during our two days with Captain Brad. He was professional, knowledgeable and just great fun to be around. The boat is well maintained and perfect for a couple to learn on. As first time boaters we weren't sure what to expect, but Captain Brad did such a great job explaining everything that we felt confident in our abilities after only two days. If you look around you will realize that they are competitively priced (MUCH cheaper than other companies operating in the keys) and are worth every penny. We can't wait to go back for our ASA 103 and 104 certificates. Thanks again for introducing us to this amazing sport. We are hooked! read more

TL; DR - Awesome trip; would recommend. My girlfriend and I joined Capt. Brad and First Mate Bruce on the Kindred Spirit (a 36' Hunter Legend) for a 4-1/2 day trip out to the Dry Tortugas and back, with an ASA-101 sailing class completed on the way. Day 1 - After driving down from Miami, we were headed out from the dock by 3:00 for a brief stop at the fuel pier and our first leg to Boca Grande Key, where we anchored for the night. Our sailing lessons began right off the bat, as Captain Brad had us each take the wheel. Day 2 - We sailed the rest of the way to the Dry Tortugas, and made our way into the anchorage off of Garden Key. We learned about different sail configurations as we made the downwind run. After a beautiful sunset, we had dinner, played a game or two, and called it a night after taking in the stars for a bit. Day 3 - We spent a couple hours in the morning practicing various skills required for ASA-101, including tacking, anchoring, and crew-overboard drills. There was a nice steady breeze and Kindred Spirit kicked up her heels whenever we brought the sails up - the first surge when she began to get underway was always an exhilarating moment. After lessons, we headed in to Garden Key to join the tour of Ft. Jefferson (the ferry from Key West gets in around 11:00, and the tour starts not long after). The tour guide - from the ferry Yankee Freedom II - was phenomenal, and had a lot of great information about the history of the fort, why it was built, how it was built, and what life was like (spoiler alert - not great). While the folks from the ferry headed back on-board for lunch, and their return trip, we spent more time wandering the fort and snorkeling around the walls, which drop down into the water. There was some sediment kicked up by other snorkelers, so the water wasn't crystal clear, but it was enough to see the fish, coral, and sea fans that were making their homes around and on the fort walls. After wrapping up there, we motored over to Loggerhead Key, to snorkel a shipwreck there. Not only was the wreck beautiful, with a ton of life and interesting coral formations, but it was also an experience that you just can't get if you're going out for the day on the ferry, so it definitely ranks as one of the best parts of the trip. On our way back to the anchorage at Garden Key, we made a short stop on shore, checking out the lighthouse that is there, and the view from the west side of Loggerhead (which faces nothing but 900+ miles of water before you hit Mexico). There were some bugs on the island (my girlfriend got bit; I was ok), so that might not be so great for some folks, but it was kind of fun walking around an island and realizing that we were the only two people on the entire island. Day 4 - The sun rose just to the north of Ft. Jefferson, and seeing the silhouette of the fort with the red and gold colors reflected off of the clouds easily ranks as one of the best sunrises I've ever seen. This day was spent mostly motoring back to Boca Grande as the winds were against us. We made it to Boca at dusk, had dinner, and tumbled into bed for our last night after sea (after once more admiring the night sky, of course). Day 5 - The last day of our trip was again mostly under power, with an assist from the mainsail when our course and the wind lined up. We made it into the marina not long after noon, and bid Kindred Spirit a sad farewell. Before making our way back north, Capt. Brad was kind enough to give us a tour of the boat he lives on, and Southermost Sailing School's teaching boat (the 26' Hunter Legend). Things to bear in mind: 1. For me, the best thing about our experience was combining the trip with the sailing lesson. I know the minimum length is three days to go to the Tortugas, but if you can make it a longer one and knock out some classes on the way, it is well worth it. 2. This is not a five-star luxury cruise ship. It's a sailboat; a very nice sailboat, but you have to work together to make it go. I'm sure we were more involved with it since we did the class, but as Capt. Brad will tell you - and as I'll tell my friends when I have a boat (someday!), everyone works on the boat. If you want a king-size bed and 30-minute showers everyday, it might not be the trip for you. 3. Capt. Brad was a fantastic source of knowledge on the area, on sailing, and on the lessons he's learned (the hard way) over his many years of sailing. I'm hoping to get back to down to Key West (or maybe the Bahamas...) at some point to knock out the next couple sailing courses with him. Bruce is one of the most laid-back guys I've ever met, and has a great sense of humor. I hope to sail with him again, and you can count yourself as lucky if you get the chance to. 4. I really, really want a 36-foot Hunter Legend now... that's a fun boat. Be aware that you might find yourself looking at boat for-sale listings on the way home. read more

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Come by plane, train or automobile but get here quick to do a private charter sail with Capt.Brad. We were totally in the dark about how to go about chartering and if it wasn't for a referral from a friend who took lessons from Capt Brad, we would have been stuck on a Fury boat with a bunch of other tourists. Brad and his lovely wife Cheryl are a joy to work with. They took into consideration our needs and wants and made suggestions as to when we should depart and how long we should go out. Brad met us at the marina store (a short ten minute ride from key west proper) and even let us board a good fifteen minutes early. We were allowed to bring snacks and drinks and Brad thoughtfully provided a cooler filled with ice and bottled water. A short check of all the safety features and we were off! Sailing! Brad is very knowledgable about the waters and the keys and offered great stories about what we passed by and the history of the place. He made sure we were comfortable and safe the entire time...my favorite part was using the step ladder to "drag" behind the boat. We were able to go to a calm spot to snorkel and Brad had great top notch gear for us to use. We saw a ton of different fish and even some wild dolphins! Our ride back was just as nice and we got to sit together on the bow and watch as the moon came up. To top off his first class service, Brad saw that we were waiting for a taxi and offered to drop us off in key west! If you are looking for the best private sailing charter experience, look no further than this! Call today and book tomorrow. You won't regret it. read more

I recently took ASA 101 - 104 with Captain Brad and what an experience it was. Not only did I learn a TON of information (and most of which only an experienced captain would know) but it was an absolute treat learning it. Captain and his wonderful wife Sherri were amazing, they even invited the student I was taking the classes with and myself on their personal boat to sail out to watch a Christmas Boat Parade. If you're thinking about learning sailing, adding something to your vacation (this is way better then jet skiing), or shopping around for the best deal on ASA certs, These are the people you should go with! They're Incredible people I now consider friends! read more