Learn to Sail! Embark on Your Sailing Adventure Today with Indiana's #1 Destination for Adult Beginners!
Thought about sailing, but never knew where to start? We're here to help. At Dauntless Sailing School our focus is on adult beginners with little or no experience who want to discover the fun and adventure of sailing. Join over 1,600 adults who have discovered the joy of sailing with Dauntless Sailing School. We turn sailing dreams into reality.
What We Offer
01
Sailing Classes for Every Level
Whether you’re stepping onto a sailboat for the first time or polishing your skills for long-term cruising, our adult-focused classes are designed for real-world learning. We specialize in helping beginners build confidence and capability — and guiding more experienced sailors toward mastery. From day sails to retirement dreams of ocean passages, we’re here to help you sail your course.
🧠Perfect for: New sailors, returning sailors, and couples preparing for cruising life.
02
Sailing Regatta Racing with Team Undaunted
Looking to take your sailing to the next level? Race with purpose as part of “Team Undaunted,” where you’ll learn how to trim sails for speed, understand racing rules, and work as a coordinated crew. Whether you’re chasing a trophy or just the thrill, you’ll gain hands-on experience — and have a blast doing it — under the guidance of Captain Todd.
⛵ Sharpen your sailing, join the team, and experience the adventure of real regattas.
03
Sunset Sailing Cruises on Geist Reservoir
Pack some hors d'oeuvres and bring your favorite bottle of wine, beer, or spirits. Join Capt. Todd aboard "Dauntless" for an unforgettable sailing cruise on Geist Reservoir. As you glide past stunning waterfront homes at sunset, you’ll enjoy an unforgettable atmosphere — whether it’s an anniversary, date night, girls’ night, or a special occasion with friends. The luxurious waterfront homes of this suburb set the perfect backdrop for a memorable celebration.
🌅 Celebrate, unwind, connect, and create lasting memories — all under sail.
04
Exclusive Caribbean Sailing Adventures
Escape to the turquoise waters of The Exumas on a private 7-day sailing adventure aboard a 46-52 foot luxury catamaran. With a professional chef curating all meals, luxurious accommodations, and a guided tour through one of the Caribbean’s most breathtaking island chains, this experience blends adventure and sailing. Snorkel reefs teaming with marine life, explore hidden beaches, and relax from sunrise to sunset in barefoot elegance.
🌴 Your dream sailing vacation — elevated to an unforgettable escape.
Why Dauntless Sailing?
Best Value, No Compromises
Our Adult Beginner Course includes six immersive, on-the-water sessions, and our advanced programs offer over a dozen. Short or "Intensive" courses don't cut it. Our courses are specifically structured to provide the time you need to learn the content and really assimilate your new skills.
Sailing shouldn’t be a luxury — it should be an adventure anyone can access. At Dauntless Sailing School, we believe unforgettable experiences on the water should be possible for every income level. Our offerings are affordably priced and provide maximum value. Even our premium Caribbean excursions are priced to be within reach.
💡 Learn more, sail more, and spend less — without sacrificing quality or your learning experience.
Hands-on, Experiential Learning
You don’t learn to sail by watching videos — you learn by doing. From your very first day with Dauntless Sailing School, you’ll be on the water, at the helm, hoisting sails, trimming lines, and making real decisions under real sailing conditions. Our experiential approach ensures you gain the competence and confidence that only hands-on learning can provide.
🧠This is not a classroom. This is your onboard, on-the-water training ground.
A “Big Boat” Adventage for Beginners
"You learn to sail in a small boat and 'graduate' to a bigger boat, right?" Wrong! Only if you want to be uncomfortable, unsafe, and potentially wet from capsizing.
At Dauntless Sailing School you will begin your sailing journey aboard a yacht built for comfort, stability, and real-world cruising. All courses take place on Dauntless, a 28’ performance cruiser equipped with wheel steering, modern electronics, a full galley, standing headroom below deck, a private head, and sleeping accommodations for five. A larger sailboat offers a smoother ride, better stability, and more forgiving handling — the perfect platform for new sailors to learn with ease, comfort, and confidence.
⛵ Bigger boat. Better experience for beginners. Built for your learning ease and success.
Experienced, Certified Instructors
...Who Teach with Heart and Passion. Don’t learn from someone who just knows how to sail — learn from someone who knows how to teach sailing. Our certified instructors bring decades of real-world, hands-on sailing experience, but more importantly, they specialize in understanding how to help beginners become confident sailors. They remember what it’s like to be a beginner and excel at breaking down the sometimes complex concepts of sailing into simple, practical skills.
Whether you’re hoisting a sail for the first time or preparing for a retirement of passage-making, you’ll be guided with patience, clarity, experience, and unmatched expertise.
🎓 Decades of experience. A passion for teaching. And a commitment to your success.
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