Hands-on lessons and private coaching with options for beginners, intermediate sailors, and customized private sessions.
Try a private lesson, book tailored one-on-one training, or enroll in structured 16-hour beginner and intermediate courses.
water-activities · New Orleans
Try Sailing Private Lessons is a short, certified intro session with Captain Matt that helps you decide if sailing fits your life. Two hours, small groups and US Sailing-aligned curriculum make this an ideal low-commitment test sail in New Orleans.
Kilroy Sail Training is a New Orleans-based sailing school that provides practical, hands-on instruction for beginners and intermediate sailors. The program lineup includes a discounted Try Sailing private lesson led by Captain Matt, which lets prospective students experience sailing firsthand before committing to a longer course. Private Lessons are available and tailored to individual goals—whether a student wants to learn basic handling, docking, or preparation for Gulf cruising. These lessons can be delivered on a student’s own boat or aboard Kilroy’s vessels.
Beginner Sailing is a structured 16-hour course with small class sizes that cover seamanship, sail trim, basic navigation, safety, and on-the-water confidence-building exercises. Intermediate Sailing is also a 16-hour course that builds on fundamentals with more advanced maneuvers and personalized coaching to increase sailors’ competence and comfort underway. Classes emphasize hands-on practice, instructor feedback, and small groups to ensure focused attention. Operating from New Orleans, Louisiana, Kilroy Sail Training focuses on practical, safety-minded instruction appropriate for the region’s local waterways and for sailors planning Gulf passages.
The business prioritizes a supportive learning environment where students learn by doing, build confidence, and develop skills for recreational sailing or cruising. Program descriptions are factual and outline course structure, scheduling flexibility for private lessons, and Captain Matt’s involvement in the Try Sailing option. Prospective students can select from single-session Try Sailing, customized Private Lessons, or structured 16-hour Beginner and Intermediate courses to match their current ability and goals. Scheduling and registration details appear on Kilroy Sail Training's public listing online.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Sail from local waters
Options for all skill levels
Core beginner & intermediate courses
Customized one-on-one instruction
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Kilroy Sail Training listing.
Kilroy Sail Training offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Book a discounted Try Sailing private lesson with Captain Matt, schedule a private session, or enroll in a 16-hour beginner or intermediate course to build real skills.
boat-charters · New Orleans
Two-hour, fully customizable keelboat coaching in New Orleans—learn docking, sail trim, and coastal cruising techniques on your boat or theirs. Ideal for beginners and owners prepping for Gulf passages.
water-activities · New Orleans
Spend 16 hours learning to sail on New Orleans waters with a 4:1 student-instructor ratio. This hands-on course covers safety, helming, sail trim, knots, docking, and man-overboard recovery—perfect for new sailors and travelers wanting to get out on the water.
water-activities · New Orleans
Take your sailing beyond the basics with a focused 16-hour Intermediate Sailing course in New Orleans. Small classes and on-water repetition build the reefing, trim, and anchoring skills you need to helm confidently in Gulf-adjacent waters.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.