Learn to Sail and Earn Sailing Certification in 3 DaysSmiling on a boat

From Southwest Florida’s Tampa Bay and barrier islands on the Gulf of Mexico to the tropical trade winds of the Caribbean, Offshore Sailing School provides a variety of rewarding Learn to Sail Courses and Sailing Certification in just 3 days.

Weekend and Week-day Course Schedules Available

A learn to sail holiday in Florida and the British Virgin Islands requires no prior experience. The Learn to Sail 101 course is a three-day program that takes you from learning the basics of sailing to how to confidently make a 26′ sailboat move through the water comfortably in any conditions.

Weekend Learn to Sail 101 Schedule at Two Florida Locations

At these two Florida locations you can take the course over a weekend.

  • Arrive Thursday late afternoon
  • Learn all day with a break for lunch Friday/Saturday/Sunday
  • Depart for home Monday or stay a couple of extra days to enjoy the Gulf Coast of Florida

Or take the Learn to Sail 101 course on weekdays and spend the rest of the week on a very relaxing vacation in sunny, warm weather.

  • Arrive Sunday late afternoon
  • Learn all day with a break for lunch Monday/Tuesday/Wednesday
  • Depart for home Thursday or stay extra days and play

What You Will Learn in the Learn to Sail 101 Course

Aside from learning all the terminology, the dynamics of being on a boat with a sails above and a keel below, all designed to effectively keep the boat upright and sailing gently with wind pressure in the sails, you will learn far more than you thought possible in just three days.  Here are the highlights:

  • How to steer a sailboat
  • How to set the sails to capture the wind and glide through the water without the aid of a motor or engine
  • How to work with others together as sailboat crew to make a sailboat move seamlesslyA man learning to sail
  • How to use a tiller to change a sailboat’s direction
  • How to give commands as a sailboat skipper and how to take commands working as crew
  • How to easily change a sailboat’s course by adjusting sails
  • How to reduce sail area to sail more comfortably when experiencing a lot of wind

All beginner sailing courses are taught by professional sailing instructors, with no more than four sailing students on each boat. If you would like a private “Buy-the-Boat” family course you may bring a total of five to take the course together. Learn to Sail instruction package rates vary by season and include tuition and accommodations ashore. If you live near the location you choose or have other options, ask for the tuition-only rate.

Offshore Sailing School graduate benefits include US Sailing membership, discounts on future courses, up to 15% discount on charters with The Moorings, and exciting Colgate Sailing Adventures® hosted flotilla vacations.

START LEARNING NOW!

Learn to Sail and Earn US Sailing Basic Keelboat Certification

The comprehensive OSS 101 Three-day Learn to Sail Course takes you through the intermediate level, ready to confidently skipper and crew on sailboats up 30′ without a captain aboard.  Buy a package including accommodations at one of our resort locations, or commute from home if you live in the area. Learn more about about the 3-day Learn to Sail OSS 101 course here. For a very special women-only sailing vacation getaway, click on your location choice below to see where couples, friends, families and singles can learn OSS 101 sailing skills in the perfect vacation setting.

Learn to Sail Online Course Preparation

This valuable Online Learn to Sail Course mirrors classroom sessions in our 3-day Learn to Sail Certification course with videos, diagrams, interactive exercises, and tests. It is required if you do not have Basic Keelboat Certification 101 and wish to “test-out” of the OSS 101 course in preparation for taking the 103/104 cruising course. It is also a great way to renew your sailing knowledge if you haven’t sailed in awhile.Family on a sailboat

Combine Learn to Sail and the Next Step – Big Boat Cruising Certification – in a Fast Track® Sailing Adventure

OSS 101/103/104 Fast Track to Cruising® is our most popular program. In 8 rewarding days, you go from couch to the captain’s chair, gaining the confidence to helm your own 40′-50′ catamaran sailboat or monohull yacht or while charter cruising in exotic cruising ports. You gain earn three US Sailing certifications: Learn to Sail 101, Basic Cruising 103 and Bareboat Cruising 104, plus your Catamaran Endorsement 114 if learning on a catamaran sailboat. And you graduate with skills and knowledge to take the helm and go sailing on live-aboard cruising boats with confidence.Boaters smiling at the camera

Anyone who is looking for a top-notch, unforgettable, hands-on experience should take an Offshore Sailing School course! Our instructors were Amazing!! They were incredibly patient, encouraging, knowledgeable, positive, helpful, professional and CALM! We were impressed with the variety of teaching techniques used to make learning fun and interesting for us both. The course exceeded our expectations in every way.

S&S Rutherford – Thamesford, Ontario

Read more testimonials here

Value-priced Family Fast Track® to Cruising Package

Our popular Fast Track to Cruising® Course is available at all locations. as a value-priced family Fast Track to Cruising package. In this sail and learn adventure, a family of 4* (two adults and two family kids, minimum age 12, maximum age 25) enjoy the full course at a special Family Cruising package price.  First you learn sailing basics on a Colgate 26, then board a 44′-48′ monohull or 40′-45′ catamaran yacht and learn how to skipper and crew a big cruising yacht while living aboard for the next 6 days.  This special offer is a delightful bonding opportunity, learning the skills to bareboat charter or go sailing and cruising on your own boat on countless future boating vacations together!

Book Now!
CALL 800-221-4326 or 239-454-1700
Sail@OffshoreSailing.com

Call 888-454-7015 or 239-454-1700 for availability and monohull or catamaran pricing.

*Fifth family child between age 12 and 25 may be added for additional fee. For nights you spend at the hotel while learning to sail, ask about availability and upgrade costs for two-bedroom suites if preferred.

Test the Waters with a Sailing Lesson

Just want to find out what sailing is all about? Two-hour or longer sailing lessons are a great way to “test the waters” and learn how much fun sailing truly is. Available at most Offshore Sailing School locations during off-season periods, cost is $125 per person per hour ($250 minimum for two-hour lesson). To learn more, please download this PDF describing in more detail what you learn in short sailing lessons.


TALK TO A SAILING ADVISOR

Discover the Joy of Sailing: Expert Sailing Instruction for Adults

Are you yearning for the freedom and excitement of sailing? At Offshore Sailing School, we transform your dream of mastering the seas into a tangible reality. With over 60 years of experience, Offshore Sailing School provides exceptional sailing education for adults of all skill levels, from novices to seasoned boaters. Our courses are meticulously crafted to build your confidence and expertise on the water, ensuring sailing experiences that are both safe and exhilarating.

Who Our Learn to Sail Courses Are Designed For

Our learn to sail courses are ideally suited for:

  • Adults of any age with a thirst for adventure
  • Families with youngsters 7 and up who want to learn together.
  • Beginners with no prior sailing experience.
  • Experienced sailors seeking to refine or renew their skills and gain certifications.
  • Individuals dreaming of sailing vacations and flotilla bareboat cruising adventures.
  • Organizations in search of distinctive team-building activities.

What You’ll Learn in Your First Days on the Water

In just a few days with Offshore Sailing School, you’ll grasp the essentials of sailing, including:

  • Fundamental sailing terminology and techniques
  • Proficient sailboat handling and maneuvering techniques
  • Critical safety procedures
  • Essential navigation basics

Hands-On Training That Builds Confidence

Award Winning Sailboats

Our learn to sail courses are taught on award-winning Colgate 26 keelboats. Choice of the US Naval Academy for training plebes and intercollegiate sailboat racing, these fast and fun daysailers have large cockpits with ergonomic seating, a special station for the instructor, and controls and sails found on large cruising boats for easy transition to next-step courses.

Water-Based Instruction for Real-World Experience

At Offshore Sailing School, we champion the philosophy of learning by doing. Our courses emphasize practical, hands-on experience on the water, providing you with the real-world training necessary to become a confident and capable sailor. You’ll gain exposure to day sailing, encounter marine life, and develop a deeper appreciation for the basics of sailing through direct interaction with the sea and sails. These are not just lessons — they’re unforgettable life experiences that build true competence.

Learn Sailboat Handling, Safety, and Navigation

Our expert US Sailing Certified Instructors will expertly guide you through every facet of the learning process, from basic sailboat handling to navigation techniques. You’ll discover how to:

  • Master steering a sailboat and sail trimming for peak performance
  • Navigate accurately using charts, a compass, and basic navigation tools
  • Adapt effectively to varying weather and wind conditions
  • Manage emergency situations with assurance, guided by fundamental navigation rules

We also teach the language of sailing and essential sailing terminology so you can communicate with confidence on board. Each sailing lesson is designed to build your knowledge of sailing, preparing you for every leg of your sailing journey.

Small Group Classes with Personalized Attention

We maintain small class sizes to guarantee that you receive personalized attention from our experienced instructors. This tailored approach allows you to learn at your own pace and receive the individual support you need to thrive — whether you’re taking a group course or a private lesson. With plenty of time on the water and one-on-one feedback, you’ll leave each day of class feeling more skilled and more confident.

Beginner-Friendly Courses with a Clear Path to Progress

  • Beginner-Friendly Sailing: Step-by-Step Learning for New Sailors: Our learn to sail courses are thoughtfully designed to be beginner-friendly, employing a step-by-step approach that makes learning both easy and enjoyable. We start with basic sailing skills and progressively build your abilities, ensuring you establish a solid foundation in the art and practice of sailing. Offshore Sailing School is committed to your success — whether you’re a beginner sailor or someone seeking a refresher before your next sailing adventure.
  • Fast Track® Learn to Sail Options: Eager to accelerate your learning? Our Fast Track® sailing courses enable you to go from novice to certified cruising sailor in as little as eight (8) days. These intensive programs deliver a comprehensive sailing experience that covers hands-on sailing classes, safety, and navigation. You’ll meet competency standards while enjoying an awesome experience filled with sunshine, beautiful beaches, and your first taste of amazing sailing.
  • Advance Your Sailing Skills: Once you’ve mastered the fundamentals with Offshore Sailing School, we offer a wide range of advanced courses to help refine your sailing goals. Whether you’re interested in coastal waters exploration, preparing for charter vacations, or setting out on the ultimate wanderlust adventure, we offer courses that match your level of experience and ambition. These programs take your sailing practice to the next level with deeper instruction and real-world scenarios.

Why Choose Offshore Sailing School

  • Over 60 Years of Teaching Excellence: With over 60 years of experience, Offshore Sailing School has a proven track record of excellence in sailing education. We’ve empowered thousands of individuals to learn to sail and achieve their sailing dreams.
  • Courses Designed by Olympic Sailor Steve Colgate: Our courses are designed by Olympic sailor Steve Colgate, guaranteeing that you receive the highest quality instruction available. Steve’s expertise and passion for sailing are evident in every aspect of our curriculum.
  • Passionate Instructors and a Proven Curriculum: Our instructors are passionate about sailing and dedicated to your success. They bring a wealth of knowledge and experience to the classroom and on the water. Our proven curriculum combines theory with hands-on learning, providing you with a comprehensive and effective sailing education.

Begin the Adventure of a Lifetime with Offshore Sailing School

Ready to learn how to sail and turn your dreams into reality? Offshore Sailing School offers hands-on training, expert instruction, and nationally recognized certification to help you gain the skills and confidence to navigate any course. Whether you’re sailing for fun, adventure, or a new lifestyle, your journey starts here. Contact us today to speak with a sailing advisor and reserve your spot in one of our exciting programs!

Frequently Asked Questions

What certifications does Offshore Sailing School offer?

Offshore Sailing School provides a comprehensive suite of US Sailing certifications, catering to sailors from beginners to advanced levels. All courses included safety techniques, especially crew overboard recovery should that ever happen:​

  • OSS 101 – Learn to Sail/Basic Keelboat: Ideal for newcomers, this course covers fundamental sailing skills. Basic Keelboat Certification.
  • OSS 102 – Performance Sailing: Focuses on enhancing sailing techniques, and boat handling in preparation for competitive sailing. Performance Sailing Certification.
  • OSS 103 – Basic Cruising: Introduces sailors to cruising fundamentals on live aboard sailboats, including sail trim, steering, navigation and onboard systems. Basic Cruising Certification.
  • OSS 104 – Bareboat Cruising: Prepares sailors for independent cruising and bareboat cruising vacations, emphasizing handling heavy weather, boat systems, planning and execution. Bareboat Cruising Certification.
  • OSS 114 – Catamaran Endorsement: Specializes in multihull sailing, teaching the nuances of catamaran handling. Catamaran Cruising Endorsement. 
  • OSS 105 – Coastal Navigation: Delves into navigation techniques essential for coastal cruising. Coastal Navigation Certification.
  • OSS 106 – Coastal Passage Making: Equips sailors with skills for extended coastal passages. Coastal Passage Making Certification.
  • OSS 107 – Celestial Navigation: Teaches traditional navigation using celestial bodies, vital for offshore sailing. Celestial Navigation Certification.
  • OSS 108 – Offshore Passage Making: Prepares sailors for long-distance offshore voyages, focusing on advanced seamanship. Offshore Passage Making Certification.
  • OSS 109 – Performance Racing: Aimed at competitive sailors, this course hones racing strategies, techniques and tactics.​
  • 111 – Boat Handling & Docking: For monohull or catamaran sailors who want to learn more about and practice maneuvering in tight quarters and docking in all wind and tide conditions. 
  • 112 – Fast Track to Power Cruising:  The ultimate big boat power boat course, prepares boaters for bareboat chartering on live aboard power boats anywhere in the world. US Powerboat Cruising Certification.

Our course certifications are recognized internationally and are structured to build upon each other, ensuring a progressive learning experience. Additionally, Offshore Sailing School offers many weekend refresher courses an IPC Prep course, assisting sailors in obtaining the International Proficiency Certificate (IPC) required for chartering in certain countries.​

Do I need prior experience to take a learn to sail course? 

No prior experience is necessary. Our courses are designed for beginners.

What is included in the Offshore Sailing School course fee? 

The course fee includes instruction, course materials, and use of our training yachts.

What should I bring to the Offshore Sailing School course? 

We’ll provide you with a detailed packing list, but essentials include comfortable clothing, non-slip shoes, sunscreen, and a hat.

What if I need to cancel my Offshore Sailing School course? 

Our cancellation policy is outlined in our terms and conditions.

Can I charter a sailboat after completing the Offshore Sailing School courses? 

Yes, when you complete our monohull, catamaran, or powerboat cruising course, our certifications are recognized by charter companies worldwide.

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888-454-7015     or    239-454-1700

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