Island Sailing's program progresses from learning to sail to cruising, bareboat and advanced training. Each class introduces new theory and skills, larger boats, and sailing in more challenging conditions.

Learn to Sail
Basic Sailing Course

Sailing a Capri 22 close hauled with family

Learning the basics of sailing is easy, and once sailing you'll wonder why you waited so long to learn!

This fun 2-day Basic Sailing Course teaches you how to sail a keelboat safely and confidently. Includes 2 free days of sailing.

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Learn to Cruise
Basic Cruising Course

learn to cruise sailing with this basic coastal cruising course

Sail further and faster with the 2-day Basic Cruising Course.

Learn improved sail and boat handling techniques, including heavier weather sailing and sailing on sailboats 25' and larger. Gain your Skipper Certification.

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Learn Bareboat
Bareboat Course

Island Sailing courses, cruising and bareboat

Sail big boats and charter in exotic locations.

The 3-day charter Bareboat Course teaches a complete understanding of vessel systems, planning, and large boat handling. We train to International ICC standards.

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2 FREE sailing courses and free online sailing logbook with NauticEd

Sign-up with NauticEd > receive 2 FREE online courses, learn the basics and gain access to free online sailing resources. If new to sailing, this is an instructive and interactive introduction.

Two FREE courses. GO»

2018 Offshore “Bluewater” Voyages

2018 Offshore "Bluewater" Voyages
Offshore Passage and “Blue Water” opportunities. 
Join RYA and NauticEd instructor and catamaran expert on a 4-part delivery of a Salina 48 from Pensacola FL to Miami, Bermuda and landing in the Bahamas.
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Coastal Navigation

Practical Navigation Clinics teach the physical art of navigation while incorporating veteran navigators' tricks and techniques. Navigation is fairly easy to learn, but often more difficult to really plan and do while sailing - these clinics blend online knowledge training with practical clinics that include knowledge Q&A, practical instruction and hands-on practice. Coastal Navigation teaches you how to plan a trip, plot highly efficient courses, and avoid the multitude of hazards using a variety of tools and knowledge. When sailors learn to use currents, tides and weather to their advantage then cruising truly becomes an art. "Wind and Waves favor the ablest navigator..."
Coastal Navigation teaches you how to plan a trip, plot highly efficient courses, and avoid the multitude of hazards using a variety of tools and knowledge.
Learn practical navigation from the pros in this 3-clinic Navigation course.
Navigation info »

Spinnaker Clinic

Spinnaker Class. Learn how to sail with the spinnaker sail.
Learn to harness the power of the Spinnaker. Progress into performance sailing, or just improve your light wind skills on the gentle summer afternoons.
Hands-on spinnaker training and practice in 3-4 hr on water sessions.
Spinnaker info »

Private Sailing Instruction

private sailing instruction, sailing certification challenge
Work one-on-one with an instructor to focus on improving skills, experience and techniques.  Island Sailing works with many of the top instructors and experts in the country, and we offer many services beyond the classroom…
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International Sailing License & Credentials (SLC)

Approved SLC school. The international sailing license and credentials.
*New* International Licensing.
Earn your SLC, the recreational sailing license valid for yacht charter companies worldwide including Europe.
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International Certificate of Competence (ICC)

The International Certificate of Competence is approved by the UN resolution 40
Earn your ICC! Assessments ongoing through 2018. The ICC is the only sailing license recognized by the United Nations.
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Introduction to Sailing

introduction to sailing

Island Sailing offers a variety of options to introduce you to sailing: just going sailing with an instructor for a brief introduction, or if interested in chartering join one of our Adventure Vacations... GO»

& Offshore

advanced and offshore sailing

An offshore sailing program to learn advanced "Blue Water" techniques while sailing vessels between exotic ports.

Certifications are available, and more importantly the quality of the training you'll receive is second to none. GO»

Adventure Vacations

sailing vacation to the BVIs

Training and sun & fun: a sailing program for individuals and couples alike to receive advanced charter and near coastal... GO»

Continued Sailing Education

Continued Sailing Education. Sailing seminars and sailing clinics

The learning never stops - sailors are always expanding their skills, knowledge and experience. These sailing seminars and classes taught by experts in their fields... GO»


Sailing courses open a world of possibilities that includes many unexpected challenges. To sail competently, sailors need knowledge, practical training and experience to safely operate sailboats - three components of all Island Sailing programs. After 36 years, thousands of students and over 12,000 club sails we've learned what makes a great sailing program!


Like most of our students, we are parents and professionals pressed for time in today's busy world. So, we construct our classes to make best use of the time available: interactive online training and testing is often more efficient than books as well as frees class time. The extra class time is spent training on the water, giving students more meaningful practical instruction. And, we're flexible in that if weather doesn't cooperate or additional training is needed, we'll work with your schedule in continuing the training.


Since the dawn of time when humans first took to the seas to 'learn the ropes', much of this training was passed down from sailor-to-sailor. That part hasn't changed much in sailing's 7,000+ year history, and in our small-group instruction you're trained by a highly experienced sailor. Our on-the-water courses include licensed instructors, Small Group low student-to-instructor ratios, proper equipment and no "time limit" on course length (i.e., we guarantee competency, regardless of time - hey you pay us for training, not stickers...). Choosing a Sailing School >


What has changed is technology, and we make knowledge training easier by utilizing the latest/greatest online training systems available. NauticEd's advanced online training gives students the most up-to-date and advanced training available while increasing your practical on-the-water instruction time. For continued training - Navigation, Radar, Weather and Celestial - we offer Starpath Navigation materials and home study courses. Learn about NauticEd >


Island Sailing's practical courses exceed the standards of US based certification systems. Our affiliation with NauticEd offers paths to RYA, ICC and international certification, and with knowledge courses such as Navigation we work with the Starpath School of Navigation - which, surpasses any certification standard. Learn about certification >


Simply, we work to fulfill each sailor's goals and needs. If you're not sure or have questions, certainly contact us....


Need Help? Contact Island Sailing

Alternatively, contact Josh directly at or (503) 285-7765 with questions or for more information.

When you can't change the directions of the wind, adjust your sails