"You can't learn to sail in a classroom." - Capt. Todd Bracken

At Dauntless Sailing School our focus is on adult beginners (and those with some experience yet looking to fine-tune their skills). We help nurture every level of sailor, from those who have never stepped foot on a sailboat to the couple who plan to spend their retirement years cruising the world aboard their own sailboat. Whatever your ultimate objective in sailing, Dauntless Sailing School is where your adventure starts! 

Adult Beginner Sailing Course (Our Flagship Offering)
Our hands-on, 6-session adult beginner sailing class covers the basics of “big boat” sailing. Learn sailing fundamentals including parts of a sailboat, how to sail regardless of wind direction, basic sailing terminology, safety procedures, basic rules, anchoring and docking. By the end of the course participants are able to perform all of the tasks necessary to depart the dock, go sailing, and return to the dock with minimal or no instructor intervention. Class fee is all inclusive. All necessary safety equipment is supplied (life-jackets, etc.). Classes are forming now! Book early to reserve your spot! No previous experience is necessary.

Great Lakes Excursions
Looking for the ultimate Midwest sailing adventure on a budget? Join Capt. Todd for several days of immersive, hands-on learning and fun while port-to-port sailboat cruising on the “big water” of The Great Lakes. This "intermediate" level sailing experience builds on the fundamental skills taught in our Adult Beginner Sailing Course and adds basic coastal navigation instruction (what in nautical terms is called piloting), use of modern navigation electronics, and coastal cruising planning (course planning, boat provisioning, overnighting on-board, etc.). These excursions vary from three days to seven days based on what area of the Great Lakes we sail. Course fee is all inclusive (activities ashore not included). Pre-requisite: Adult Beginner Sailing course.

Regatta Participation
Ever fantasized about sailing in the America’s Cup? This isn’t that, but it’s close. This experiential learning opportunity is reserved only for the true sports adventurer. Participants are active racing crew members aboard “Dauntless” for a major offshore regatta. This course focuses on the educational experience, though winning is always a nice bonus. Secure your spot early - participation is limited. Pre-requisite: Adult Beginner Sailing course.

Ocean Coast Cruising Expeditions
How does island hopping in the Caribbean sound? How about a trip up the eastern coast of Ireland? Ever thought about circumnavigating Scotland (around the Highlands and back through the Caledonian Canal including the famous Loch Ness)? Coastline of France or Italy anyone? Don't have a passport? There is always the New England coast or an adventurous cruise down the Florida Keys. These expeditions vary and are organized every several years based on participant interest. Pre-requisite: Adult Beginner Sailing course.


  • I had never been on a sailboat until my first day of Dauntless Sailing School, immediately Captain Todd made me feel at home. Todd’s passion for sailing and wealth of sailing knowledge is only eclipsed by his devotion for teaching others. Within four weeks of my first class, I became a proud owner of a 23’ sailboat exploring the open sea’s “small reservoir” using the sailing skills Todd and Dauntless Sailing School thought me. Whether your interests are casual sailing and evening cruises or advanced sailing techniques and sailboat racing experience, Todd Bracken and Dauntless Sailing School are there to help.
    — Sean M.
  • My husband and I are finishing our 6-week Adult Beginner Sailing course and have had our eyes opened to a new interest and hobby. We had never stepped foot on a sailboat before Todd started his instruction with exactly that… how to properly get on and off the boat. His detailed and expert instruction continued to build from that. The class includes all of the specifics of actually sailing a boat. You are at the helm from day 1, tacking and gybeing and trying to remember which is which. Sailing on Geist Reservoir can be frustrating, shifting winds, having to consider other boats around, learning to avoid the shallow areas, however, what could be a better way for new sailors to learn the craft, then to have to get used to all of those variables at once. We highly recommend this class for beginners and those interested in learning more about sailing.
    — Jill L.
  • WOW sailing is FUN!!!! The Dauntless Sailing School developed by Captain Todd Bracken allows for an excellent way for a beginner to learn to sail keelboats. At the completion of the course I learned and experienced more than expected. The six week training program consisted of hands-on as well as discussions before and after each sailing session. I also attended the course offered on the “big water” of Lake Michigan. This two day/one night class was blessed with great weather and favorable winds. The view of Chicago from the lake was beautiful. During this class we also experienced open water sailing and the thrill of sailing close to several tall ships that were leaving the Tall Ships Festival. Todd Bracken is a knowledgeable and enthusiastic teacher who has a unique way of inspiring and informing his students.
    — Bill R.
  • Sailing in central Indiana? It seems like an almost preposterous concept, but I’m here to tell you, friends, it can be done! Get yourself some soft-soled shoes, your most nautical striped top and a copy of “Basic Keelboat” and sign up for a session with the Dauntless Sailing School. This school operates on a 28-foot sailboat on Geist Reservoir. Captain Todd will teach you the basics of sailing on his pretty boat, and you and your classmates will attempt to crew it for six weeks. Hijinx will ensue. I took the fall class—sadly, this fall was characterized by little wind. Still, on windless nights we learned about anchoring and boat safety and the strange history of the reservoir itself. You’ll learn to tie knots and use all the esoteric language of the sea! Impress your friends by knowing how to break a Bowline knot and how to tell the difference between a jib and a genoa (and how to use them!). This class is pretty much a must if you’re looking to buy a boat (not my tax bracket) or if you just want to learn the basics of sailing (that’s me). Beware that fall sailing will occur mostly in the dark, and get cold toward the end of the session. Supposedly there’s more wind in the fall, though unfortunately that didn’t pan out for my class. The teacher is quite the character, and he does allow you to party on the boat if you want. Sadly, my group had a kind of collectively uptight vibe, which I think was a bit of a disappointment to the instructor. I honestly wish I could take this again, probably in the summer, with five of my closest friends.
    — Emily U.
  • I recently read a line in a novel stating the ocean “was beautiful and fearful at the same time”. That is how I felt and still feel about sailing! My husband wanted to take sailing lessons as we look toward our retirement years, and I thought I would join him. We had sailed a small sunfish prior to having children, and I was looking forward to the experience. I was quite surprised to walk up to this 28’ vessel that we would be learning to sail! I loved the entire experience even though I was more than a little scared when we would fly through the water at 7 and 8 knots. Todd is a patient and knowledgeable captain and has given us wonderful information to pursue this new found love of sailing. My husband and I are now looking to purchase a boat, and I told him I wanted it as similar to the Dauntless as possible. I love the size and feel of the boat and am very comfortable with it. The best part is Todd let us know he will be there for us to help us get started with our new toy!
    — Glenda G.

Sailing Course Photos