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America’s #1 Sailing School
Luxury‑level training, Real‑world Seamanship
Sail. Learn. Discover. The world’s finest sailing instruction experience
60 years of legacy, 160,000 sailors trained, and a future shaped by excellence on the water
160k+
STUDENTS TRAINED
Celebrating Over 60 Years of Sailing Excellence.
Established in 1964, Offshore Sailing School has spent six decades building a reputation for quality, safety, and excellence in sailing education. Now under the leadership of Brian Crotty, the school is entering a new chapter, modernizing its fleet, elevating the training experience, and expanding its programs while preserving the trusted heritage thousands of students have relied on. With certified instructors, advanced learning systems, and hands-on training for every level, Offshore Sailing School continues to set the standard for world-class sailing education.
OUR LOCATIONS
Our Mission: To Inspire Competent, Responsible Sailors.
At Offshore Sailing School, we believe sailing is more than a skill — it’s a mindset. Our mission is to make the joy of sailing accessible, sustainable, and empowering through hands-on education, advanced technology, and eco-conscious operations.
Why Sailors Choose Offshore
➢ 60 Years of Proven Expertise – Trusted by thousands worldwide.
➢ Accredited NauticEd Partner –Integration of online learning and hands-on training with globally recognized certification.
➢ Modern Fleet & Facilities – Experience sailing on luxury monohulls and catamarans.
➢ Personalized Learning Approach – Small group sessions with certified instructors.
➢ Real-World Experience – Practical, hands-on training designed for confidence at sea.
Committed to a Sustainable Future
Our courses incorporate eco-friendly anchoring and waste management, reduce carbon footprints through wind-powered travel and support marine conservation efforts.
By integrating sustainability into our sailing programs, we empower sailors to protect the waters they explore.
Great Vacations Start with the Perfect Course
GO FROM THE COUCH TO THE CAPTAIN’S CHAIR IN ONE WEEK!
See What Our Graduates Are Saying
Jhon Schepler
AMES. IA
“Time well spent! Definitely will be back for more. Our instructor was excellent, patient and quick to act when assistance was needed.”
OSS 101
LEARN TO SAIL
Shea Gottshall
CHARLOTTE, NC
“Such a great experience, amazing trip and class! I learned much more than I ever thought possible. Great instructors, incredibly knowledgeable in all aspects of sailing, patient and detailed in their lessons. I recommend this program to anyone interested in learning about sailing, particularly for a novice like me.”
OSS 101/103/104 /114
Fast Track® to
Catamaran Cruising
Mark Walts
MUSKEGO, WI
“Offshore made it easy to learn! From easing us through the many tactical details related to arrival and expectations with extensive email communications, to the excellent books to the truly remarkable instructor who made learning a joy – the Fast Track to Cruising was one of the best weeks ever. Great memories, excellent skills development. What more could one ask for?”
OSS 101/103/104
Fast Track® to
Catamaran Cruising
Jacques Mayo
LIMA, PERU
“Our instructors were excellent. They let the students try many new things by themselves that increased our confidence level. They were very patient and reassuring. We had a tough passage from Miami to Captiva via Key West in bad weather. The sailing was difficult, and the learning experience was outstanding.”
OSS 107/108
Fast Track® to
Offshore Cruising
Harry Belk
SPARTANBURG, SC
“Money well spent. Would do it again, but I don’t need to! After only 5 days of classroom and power cruising time, I feel confident that I can better handle my boat in a variety of situations.”
OSS 109
Fast Track® to
Power Cruising
Kristin Mahendra
ST. CHARLES, MO
“My instructor’s overall enthusiasm for sailing was so contagious, he has me addicted to sailing and craving more! He did an amazing job identifying my strengths and weaknesses in the classroom and on-water, and tailored his teaching to meet my needs and abilities.”
OSS 101
LEARN TO SAIL
Courtney Stroot
KELLER. TX
“That’s me steering a big catamaran. It was absolutely the best seven-day adventure ever. An amazing instructor, exuded knowledge, skill and most of all, patience. I loved rafting up with the other students from the class.”
OSS 101/103/104/114
Fast Track® to
Catamaran Cruising
Wyatt Blasingame
MORRISON, CO
“My wife and I had an absolutely wonderful experience in the Fast Track to Cruising Course in the British Virgin Islands. The instructors were excellent – extremely knowledgeable and patient. I had some small boat experience and my wife was a complete novice, but we’re now comfortable and excited to take our first bareboat charter on our own.”
OSS 101/103/104
Fast Track® to
Cruising
Naomi and Jeff Weingart
WESTPORT, CT
“Time well spent! Definitely will be back for more. Our instructor was excellent, patient and quick to act when assistance was needed.”
IOSS 101/103/104 /114
Fast Track® to
Catamaran Cruising
Merzi Dubash
OLD BRIDGE, NJ
“This is the second time I’ve taken the Learn to Sail course. The last was 10 years ago. The experience was awesome. My instructor was excellent, gave me plenty of opportunity to practice, and never shied away from answering questions. In 3 days, he provided all the knowledge needed to sail. I recommend this course for any sailing enthusiast.”
OSS 101
LEARN TO SAIL
Master the Art of Sailing with Offshore Sailing School
For over 60 years, Offshore Sailing School has delivered professional, hands-on sailing education for sailors of all levels. Our proven curriculum, expert instructors, and modern training fleet prepare you for real-world sailing with confidence.
How We Teach: Hands-On Learning for Maximum Skill Development
We teach by doing. Every course combines essential theory with on-the-water training, so students actively learn sail handling, navigation, docking, and safety; building skill and confidence efficiently.
Master the Science of Sailing and Navigation Skills
Our structured curriculum covers:
- Wind dynamics and sail aerodynamics.
- Tides, currents, and weather patterns.
- Coastal and celestial navigation skills.
- Safe docking and anchoring techniques.
Whether you’re mastering basic sailing or advancing your knowledge, our courses build a deep understanding of sailing principles.
Achieve Recognized Sailing Certifications
Our courses are designed to equip you with the credentials needed for various sailing endeavors, from recreational sailing to professional maritime pursuits.
Unforgettable Sailing Vacations and Flotilla Adventures
Combine learning with leisure through our sailing vacations and flotilla cruises. Explore exotic destinations while honing your sailing skills under the guidance of experienced instructors.
Corporate Team Building and Leadership Programs
Engage your team in activities that promote collaboration, strategic thinking, and effective communication, all set against the backdrop of an exhilarating sailing experience.
Fleet and Training Yachts for Every Course
Offshore Sailing School provides a fleet of well-maintained yachts specifically designed for training purposes. Our fleet includes monohulls, catamarans, and powerboats, ensuring students receive instruction on the right vessel for their learning objectives.
Start Your Sailing Adventure Today
Take the first step toward sailing confidently with Offshore Sailing School. Enroll in a course, plan a sailing vacation, or participate in a team-building experience. Contact us today to begin your journey with a sailing academy that prioritizes practical learning, expert instruction, and real-world experience.
Frequently Asked Questions
What skill levels do Offshore Sailing School courses accommodate?
Offshore Sailing School offers programs for all skill levels, from beginners learning sailing basics to advanced sailors preparing for offshore cruising or racing. Whether you are starting with basic sailing or refining your navigation skills, our structured courses ensure a tailored learning experience that helps you progress confidently.
What certifications can I earn at Offshore Sailing School?
Our sailing school provides internationally recognized certifications, including bareboat cruising, coastal passage making, and powerboat handling. These certifications equip students with the credentials needed for chartering sailboats, offshore cruising, and competitive sailing.
Does Offshore Sailing School offer sailing adventures and flotilla vacations?
Yes! Offshore Sailing School offers sailing adventures, flotilla vacations, and passage-making experiences. These programs combine structured learning with exciting travel destinations, allowing students to build their sailing skills while exploring scenic locations worldwide.
What is the difference between sailing lessons and private sailing lessons?
Standard sailing lessons take place in a group setting with structured instruction, which is ideal for learning alongside other sailors. Private sailing lessons offer personalized training with one-on-one guidance, allowing students to focus on specific skills, whether it’s mastering basic sailing or preparing for offshore voyages.
Call Us Today!
GET IN TOUCH, ASK OUR EXPERTS ABOUT TRAINING, GROUP PACKAGES, VACATIONS, AND MORE!
Fast Track® Sail & Power Courses
Individual Sailing Course Options
Team Building Programs
DEVELOP GOOD LEADERSHIP SKILLS, TRUST AND RESPECT!
