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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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.

SAILING CATAMARAN 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.

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: Bali 4.2, Pajot Lucia 40

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: Bali 4.2, Pajot Lucia 40

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: 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.

TASTE OF SAILING

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.

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: Jeann1eau 479, Bali 4.2, Pajot Lucia 40, Aquila 50, Fountaine Pajot MY5, 350 SLX, Cruisers Yachts GLS 42, Golden Ticket

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: Jeanneau 479, Bali 4.2, Pajot Lucia 40, Aquila 50, Fountaine Pajot MY5, 350 SLX, Cruisers Yachts GLS 42, Golden Ticket

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 practical seamanship. | Available on: Jeanneau 479, Bali 4.2, Pajot Lucia 40, Aquila 50/ Memory Maker, Fountaine Pajot MY5

BAREBOAT CRUISING

Code: OSS 104 | Level: Intermediate | A four-day, three-night liveaboard cruising course designed for sailors who have completed Learn to Sail and Coastal Cruising. Students gain hands-on 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: Jeanneau 479, Bali 4.2, Pajot Lucia 40, Aquila 50, Fountaine Pajot MY5

CATAMARAN SAIL

Code: OSS 114 | Level: Intermediate | A course covering the unique aspects of sailing and managing cruising catamarans. Instruction includes multihull design, rigging, onboard systems, safety procedures, and capsizing awareness. Students practice sail handling, twin-engine maneuvering, tight-space docking, and man-overboard recovery to confidently operate catamarans 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 50, 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.

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.

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: Jeanneau 479, Bali 4.2, Pajot Lucia 40, Aquila 50, Fountaine Pajot MY5, 350 SLX, Cruisers Yachts GLS 42, Golden Ticket

INTERNATIONAL POWERBOATING LICENSE

Code: SLC-p | Level: Advanced | An internationally recognized recreational powerboating credential valid with charter companies worldwide. Requirements include online theory coursework, documented experience on similar vessels, and demonstration of practical powerboating skills in accordance with international and U.S. Coast Guard standards. | Available on: Aquila 44, Fountaine Pajot MY5

INTERNATIONAL SAILING LICENSE

Code: SLC-p | 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, Pajot Lucia 40

OUR LOCATIONS

FLORIDA

SARASOTA

FLORIDA

ST. PETERSBURG

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.

vacations on boat

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.

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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.

45' catamaran sailboat under sail

60 years of legacy, 160,000 sailors trained, and a future shaped by excellence on the water

Boats anchored off Stocking Island in Bahamas
Lakka Bay, Ionian Islands
Dark reef in clear waters with boats anchored behind

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.

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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.

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