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America’s #1 Sailing School
Expert Training on Sailing Catamarans, Power Catamarans, Sailing Monohull & Power Boats
Now under the new leadership of Seaworthy Academy
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NauticEd–Certified Sailing Education
All Offshore Sailing courses combine NauticEd theory & on-water training, taught by EDU-4–certified instructors under American National Standards. Earn credentials toward Bareboat Charter qualification, International SLC, and Mediterranean charter licensing with globally recognized certification that goes beyond just time on the water.
Bundle Courses
MONOHULL SAILING SUITE
Code: OSS 101, OSS 103, OSS 104
Level: Beginner, Intermediate
Live aboard the Jeanneau 479 while sailing the beautiful waters of Sarasota and St. Pete. This immersive week long liveaboard experience blends relaxation and learning, allowing you to enjoy the destination. Covering sailing fundamentals, coastal cruising, and bareboat chartering, you’ll earn multiple certifications through hands-on learning that feels like an adventure.
Available on: Jeanneau 479
POWERBOAT SUITE
Code: OSS 101-p,OSS 103-p,OSS 104-p
Level: Beginner, Intermediate
Spend a week on the water sharpening your powerboating skills while exploring beautiful coastal destinations. Aboard our luxury outboard-powered vessels, each day blends hands-on driving time with real cruising. Gain confidence in boat handling, close-quarters maneuvering, coastal cruising, and bareboat readiness; learning multiple certifications along the way without it feeling like a classroom.
Available On: 35′ Aviara, Sea Ray SLX 350, Monterey 385SS, Cruisers Yachts 42 GLS
SAILING CATAMARAN SUITE
Code: OSS 101, OSS 103, OSS 104
Level: Beginner, Intermediate
Sail aboard a spacious sailing catamaran for a week of sailing adventure along Florida’s Gulf Coast. Designed for sailors ready to level up, this experience pairs the freedom of coastal cruising around Sarasota and St. Pete with hands-on learning. Earn multiple sailing certifications in advanced sail handling, coastal navigation, and bareboat charter readiness; all delivered in a setting that feels more like a getaway than a course.
Available On: Bali 4.2, Fountaine Pajot Lucia 40
POWER CATAMARAN SUITE
Code: OSS 103-p, OSS 104-p,OSS 114-p
Level: Beginner, Intermediate
Spend a week cruising the coast aboard a luxury power catamaran, gaining confidence at the helm while enjoying the space and comfort of a multihull. Powered by inboard diesels, this experience blends multihull handling, systems, navigation, and charter readiness; earning credentials along the way without ever feeling like a course.
Available on: Aquila 44, Fountaine Pajot MY5
THE 360° SAILING SUITE
Code: OSS 101, OSS 103, OSS 104, OSS 114
Level: Beginner, Intermediate
Spend a full week sailing beautiful coastal waters while gaining sailing education from fundamentals to bareboat charter readiness. Aboard modern sailing catamarans, this immersive experience introduces both core sailing skills and the key differences between monohulls and multihulls, along with coastal navigation and charter preparation.
Available on: Jeanneau 479, Fountaine Pajot Lucia 40 and Bali 4.2
THE 360° POWER SUITE
Code: OSS 101-p,OSS 103-p, OSS 104-p,OSS 114-p
Level: Beginner, Intermediate
Spend a full week on the water building confidence from your first powerboating skills to charter-ready cruising. Aboard luxury power catamarans powered by inboard diesels, each day provides hands-on time at the helm, covering advanced handling, navigation, onboard systems, and bareboat readiness.
Available on: 35′ Aviara, Sea Ray SLX 350, Monterey 385SS, Cruisers Yachts 42 GLS, Aquila 44, Fountaine Pajot MY5
MONOHULL SAILING SUITE
Code: OSS 101, OSS 103, OSS 104 | Level: Beginner, Intermediate | Live aboard the Jeanneau 479 while sailing the beautiful waters of Sarasota and St. Pete. This immersive week long liveaboard experience blends relaxation and learning, allowing you to enjoy the destination. Covering sailing fundamentals, coastal cruising, and bareboat chartering, you’ll earn multiple certifications through hands-on learning that feels like an adventure. | Available on: Jeanneau 479
POWERBOAT SUITE
Code: OSS 101-p, OSS 103-p, OSS 104-p | Level: Beginner, Intermediate | Spend a week on the water sharpening your powerboating skills while exploring beautiful coastal destinations. Aboard our luxury outboard-powered vessels, each day blends hands-on driving time with real cruising. Gain confidence in boat handling, close-quarters maneuvering, coastal cruising, and bareboat readiness; learning multiple certifications along the way without it feeling like a classroom. | Available On: 35′ Aviara, Sea Ray SLX 350, Monterey 385SS, Cruisers Yachts 42 GLS
SAILING CATAMARAN SUITE
Code: OSS 101, OSS 103, OSS 104 | Level: Beginner, Intermediate | Sail aboard a spacious sailing catamaran for a week of sailing adventure along Florida’s Gulf Coast. Designed for sailors ready to level up, this experience pairs the freedom of coastal cruising around Sarasota and St. Pete with hands-on learning. Earn multiple sailing certifications in advanced sail handling, coastal navigation, and bareboat charter readiness; all delivered in a setting that feels more like a getaway than a course. | Available On: Bali 4.2, Fountaine Pajot Lucia 40
POWER CATAMARAN SUITE
Code: OSS 103-p, OSS 104-p, OSS 114-p | Level: Beginner, Intermediate | Spend a week cruising the coast aboard a luxury power catamaran, gaining confidence at the helm while enjoying the space and comfort of a multihull. Powered by inboard diesels, this experience blends multihull handling, systems, navigation, and charter readiness; earning credentials along the way without ever feeling like a course. | Available on: Aquila 44, Fountaine Pajot MY5
THE 360° SAILING SUITE
Code: OSS 101, OSS 103, OSS 104, OSS 114 | Level: Beginner, Intermediate | Spend a full week sailing beautiful coastal waters while gaining sailing education from fundamentals to bareboat charter readiness. Aboard modern sailing catamarans, this immersive experience introduces both core sailing skills and the key differences between monohulls and multihulls, along with coastal navigation and charter preparation. | Available on: Jeanneau 479, Fountaine Pajot Lucia 40 and Bali 4.2
THE 360° POWER SUITE
Code: OSS 101-p, OSS 103-p, OSS 104-p, OSS 114-p | Level: Beginner, Intermediate | Spend a full week on the water building confidence from your first powerboating skills to charter-ready cruising. Aboard luxury power catamarans powered by inboard diesels, each day provides hands-on time at the helm, covering advanced handling, navigation, onboard systems, and bareboat readiness. | Available on: 35′ Aviara, Sea Ray SLX 350, Monterey 385SS, Cruisers Yachts 42 GLS, Aquila 44, Fountaine Pajot MY5
Courses
LEARN TO SAIL
Level: Beginner | An introduction to the fundamentals of sailing. Learn sailing terminology, parts of the boat, points of sail, wind awareness, basic sail trim, knots, anchoring, docking, navigation rules, weather basics, and essential safety practices to build a strong foundation on the water. | Available on: Jeanneau 479
LEARN TO SAIL INTENSIVE
Level: Beginner | An extended version of the Learn to Sail course. Gain more hands-on experience while reinforcing core sailing skills, improving confidence, and developing comfort with boat handling, sail control, docking, anchoring, and basic seamanship. | Available on: Jeanneau 479
TASTE OF SAILING
Level: Beginner | Experience a half-day sail on the bay with hands-on participation at the helm. Unlike a traditional charter, this introductory session invites you to trim sails, steer the boat, and get a true feel for sailing. It’s the perfect way to decide if you’re ready to dive deeper and begin your sailing education.
BASIC POWERBOATING
Code: OSS 101-p | Level: Beginner | Introduces the skills and knowledge needed to operate a recreational powerboat safely. Covers boating terminology, vessel types, propulsion systems, hull shapes, safety equipment, navigation basics, docking, maneuvering, and the responsibilities of the skipper and crew in light to moderate conditions. | Available On: 35′ Aviara and Sea Ray SLX 350
PERFORMANCE SAILING SKILLS
Level: Beginner, Intermediate | Designed to refine technique and efficiency on the water. This course focuses on sail trim, balance, and boat speed, helping sailors better understand how to get maximum performance from the sails in a variety of wind and sea conditions. | Available on: Jeanneau 479, Bali 4.2, Pajot Lucia 40
ANCHORING
Level: Beginner, Intermediate | A focused course covering the principles and practical skills of anchoring. Students learn how to select suitable anchorages, understand bottom conditions, choose proper ground tackle, set and retrieve anchors correctly, and anchor safely in varying wind and sea conditions. | Available on: Available on all power and sail vessels
DOCKING
Level: Beginner, Intermediate | Teaches students how to dock confidently in a variety of situations. Instruction covers wind and current management, tight-space maneuvering, unfamiliar docks, communication techniques, and practical methods for safely approaching, securing, and departing from docks. | Available on: Available on all power and sail vessels
COASTAL CRUISING
Code: OSS 103 | Level: Intermediate | Build on foundational sailing skills while learning to operate confidently as a daytime “skipper” in moderate conditions. Instruction includes crew communication, systems awareness, auxiliary engine use, sail handling, reefing, anchoring, weather interpretation, safety, and seamanship. | Available on: All Sailing Yachts
BAREBOAT CRUISING
Code: OSS 104 | Level: Intermediate | A 4 Day 3 Night liveaboard cruising course designed for sailors who have completed Learn to Sail and Coastal Cruising. Students gain experience in piloting, navigation, dead reckoning, docking, systems troubleshooting, maintenance, cruise planning, weather forecasting, and overnight anchoring while acting as skipper or crew. | Available on: All Saling Boats
CATAMARAN SAIL
Code: OSS 114 | Level: Intermediate | Learn what makes cruising catamarans different through hands-on training in design, systems, and safety. Practice sail handling, twin-engine control, tight docking, and man-overboard recovery. Operate confidently in coastal and offshore conditions. | Available on: Bali 4.2, Fountaine Pajot Lucia 40
CATAMARAN POWER
Code: OSS 114-p | Level: Intermediate | This course provides in-depth power-cruising instruction aboard power catamarans. Students learn twin-engine maneuvering, precise docking, anchoring techniques, onboard systems, navigation, and safe coastal operation, building confidence and control when operating multihull power vessels. | Available on: Aquila 44, Fountaine Pajot MY5
INTERMEDIATE POWERBOATING
Code: OSS 103-p | Level: Intermediate | Builds on basic powerboating skills with a focus on skippering during daytime operation in moderate wind and sea conditions. Instruction includes crew communication, docking, anchoring, weather awareness, safety, seamanship, and an introduction to electrical, plumbing, and propulsion systems. | Available On: Sea Ray SLX 350, Cruisers Yachts 42 GLS, Monterey 385SS
ADVANCED POWERBOATING
Code: OSS 104-p | Level: Intermediate | Designed for experienced powerboat operators seeking increased confidence and technical understanding. This course covers advanced docking, anchoring, crew leadership, weather interpretation, safety procedures, and maintaining onboard electrical, plumbing, and propulsion systems in coastal environments. | Available On: All Power Catamarans
REFRESHER COURSE
Level: Intermediate, Advanced | A fully customizable course for students with prior sailing or powerboating experience who want to refresh or update their skills. Training is tailored with an instructor to focus on specific goals such as boat handling, navigation, docking, systems, or overall confidence on the water. | Available on: Available on all power and sail vessels
INTERNATIONAL POWERBOATING LICENSE
Code: SLC-p | Level: Advanced | A worldwide charter-ready recreational powerboating credential, recognized internationally. Complete online theory, document experience on similar vessels, and demonstrate practical skills aligned with international requirements and U.S. Coast Guard standards. | Available on: Available on Power Boats Contact Us
INTERNATIONAL SAILING LICENSE
Code: SLC | Level: Advanced | An internationally recognized recreational sailing credential accepted by yacht charter companies worldwide. Candidates complete self-paced online theory, log appropriate prior boating experience on similar vessels, and demonstrate practical sailing skills that meet international and U.S. Coast Guard standards. | Available on: Available on Sail Boats
LEARN TO SAIL
Level: Beginner | An introduction to the fundamentals of sailing. Learn sailing terminology, parts of the boat, points of sail, wind awareness, basic sail trim, knots, anchoring, docking, navigation rules, weather basics, and essential safety practices to build a strong foundation on the water. | Available on: Jeanneau 479
LEARN TO SAIL INTENSIVE
Level: Beginner | An extended version of the Learn to Sail course. Gain more hands-on experience while reinforcing core sailing skills, improving confidence, and developing comfort with boat handling, sail control, docking, anchoring, and basic seamanship. | Available on: Jeanneau 479
TASTE OF SAILING
Level: Beginner | Experience a half-day sail on the bay with hands-on participation at the helm. Unlike a traditional charter, this introductory session invites you to trim sails, steer the boat, and get a true feel for sailing. It’s the perfect way to decide if you’re ready to dive deeper and begin your sailing education.
BASIC POWERBOATING
Code: OSS 101-p | Level: Beginner | Introduces the skills and knowledge needed to operate a recreational powerboat safely. Covers boating terminology, vessel types, propulsion systems, hull shapes, safety equipment, navigation basics, docking, maneuvering, and the responsibilities of the skipper and crew in light to moderate conditions. | Available On: 35′ Aviara and Sea Ray SLX 350
PERFORMANCE SAILING SKILLS
Level: Beginner, Intermediate | Designed to refine technique and efficiency on the water. This course focuses on sail trim, balance, and boat speed, helping sailors better understand how to get maximum performance from the sails in a variety of wind and sea conditions. | Available on: Jeanneau 479, Bali 4.2, Pajot Lucia 40
ANCHORING
Level: Beginner, Intermediate | A focused course covering the principles and practical skills of anchoring. Students learn how to select suitable anchorages, understand bottom conditions, choose proper ground tackle, set and retrieve anchors correctly, and anchor safely in varying wind and sea conditions. | Available on: Available on all power and sail vessels
DOCKING
Level: Beginner, Intermediate | Teaches students how to dock confidently in a variety of situations. Instruction covers wind and current management, tight-space maneuvering, unfamiliar docks, communication techniques, and practical methods for safely approaching, securing, and departing from docks. | Available on: Available on all power and sail vessels
COASTAL CRUISING
Code: OSS 103 | Level: Intermediate | Build on foundational sailing skills while learning to operate confidently as a daytime “skipper” in moderate conditions. Instruction includes crew communication, systems awareness, auxiliary engine use, sail handling, reefing, anchoring, weather interpretation, safety, and seamanship. | Available on: All Sailing Yachts
BAREBOAT CRUISING
Code: OSS 104 | Level: Intermediate | A 4D, 3N liveaboard cruising course designed for sailors who have completed Learn to Sail and Coastal Cruising. Students gain experience in piloting, navigation, dead reckoning, docking, systems troubleshooting, maintenance, cruise planning, weather forecasting, and overnight anchoring while acting as skipper or crew. | Available on: All Saling Boats
CATAMARAN SAIL
Code: OSS 114 | Level: Intermediate | Learn what makes cruising catamarans different through hands-on training in design, systems, and safety. Practice sail handling, twin-engine control, tight docking, and man-overboard recovery. Operate confidently in coastal and offshore conditions. | Available on: Bali 4.2, Pajot Lucia 40
CATAMARAN POWER
Code: OSS 114-p | Level: Intermediate | This course provides in-depth power-cruising instruction aboard power catamarans. Students learn twin-engine maneuvering, precise docking, anchoring techniques, onboard systems, navigation, and safe coastal operation, building confidence and control when operating multihull power vessels. | Available on: Aquila 44, Fountaine Pajot MY5
INTERMEDIATE POWERBOATING
Code: OSS 103-p | Level: Intermediate | Builds on basic powerboating skills with a focus on skippering during daytime operation in moderate wind and sea conditions. Instruction includes crew communication, docking, anchoring, weather awareness, safety, seamanship, and an introduction to electrical, plumbing, and propulsion systems. | Available On: Sea Ray SLX 350, Cruisers Yachts 42 GLS, Monterey 385SS
ADVANCED POWERBOATING
Code: OSS 104-p | Level: Intermediate | Designed for experienced powerboat operators seeking increased confidence and technical understanding. This course covers advanced docking, anchoring, crew leadership, weather interpretation, safety procedures, and maintaining onboard electrical, plumbing, and propulsion systems in coastal environments. | Available On: All Power Catamarans
REFRESHER COURSE
Level: Intermediate, Advanced | A fully customizable course for students with prior sailing or powerboating experience who want to refresh or update their skills. Training is tailored with an instructor to focus on specific goals such as boat handling, navigation, docking, systems, or overall confidence on the water. | Available on: Available on all power and sail vessels
INTERNATIONAL POWERBOATING LICENSE
Code: SLC-p | Level: Advanced | A worldwide charter-ready recreational powerboating credential, recognized internationally. Complete online theory, document experience on similar vessels, and demonstrate practical skills aligned with international requirements and U.S. Coast Guard standards. | Available on: 35′ Aviara, Sea Ray SLX 350, Aquila 44, Fountaine Pajot MY5, Monterey 385SS, Cruisers Yachts 42 GLS
INTERNATIONAL SAILING LICENSE
Code: SLC | Level: Advanced | An internationally recognized recreational sailing credential accepted by yacht charter companies worldwide. Candidates complete self-paced online theory, log appropriate prior boating experience on similar vessels, and demonstrate practical sailing skills that meet international and U.S. Coast Guard standards. | Available on: Jeanneau 479, Bali 4.2, Fountaine Pajot Lucia 40
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.
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.
Great Vacations Start with the Perfect Course
DEVELOP GOOD LEADERSHIP SKILLS, TRUST AND RESPECT!
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.
60 years of legacy, 160,000 sailors trained, and a future shaped by excellence on the water
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.
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.
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!
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
