Get Started:

Call: (888) 454-7015

Sailing Certification Courses for Beginners and Small Boat Sailors

The Learn to Sail Experience

Learn to sail in Florida, or learn to sail in the British Virgin Islands and earn US Sailing Certification from expert, caring instructors. Offshore Sailing School’s comprehensive OSS 101 sailing courses are perfect for beginners and small boat sailors looking to earn basic sailing sailing certification and then continue on to gain cruising and sailboat racing skills. The OSS 101 US sailing certification course takes you through the intermediate level aboard award-winning Colgate 26 sailboats, designed for training and safety, with plenty of features to make the transition to larger boats easy. Whichever schedule you choose below, you will receive the US Sailing Basic Keelboat textbook to study before you arrive to start your course. Studying in advance is highly recommended to ensure you get maximum value from your learn to sail experience.

The Learn to Sail course was a fabulous learning experience. Loved learning to sail, especially since we began with zero knowledge of the sport. We can’t wait to take another course and continue our sailing adventure. Our instructor was excellent – great teaching skills, very knowledgeable, made learning fun.

Jill and Daniel Delmont – Cape Coral, FL

Read more testimonials here

Three-Day Learn to Sail Vacation Experience — OSS 101 Course Schedule

The popular OSS 101 Three-day Learn to Sail course includes a five-night resort stay at Florida locations, and six-night resort stay at Scrub Island Resort, Spa & Marina in the British Virgin Islands.  The first three full days you are immersed in classroom and hands-on sailing instruction, with lunch breaks each day. On the third day, you take the US Sailing Basic Keelboat Certification test, then have two days to enjoy all the other vacation activities available in the area.  The standard OSS 101 package includes resort accommodations, with tax and resort fee. You may wish to request additional nights or shorten your vacation to the first three days. We also have a “no-lodging” rate for those who live nearby.

We were worried that 3 days would not be long enough to gain comfort on the water. Our instructor was great both in the classroom and on the water. We feel confident that we are prepared to sail on our own and are ready for a Live Aboard Cruising course! Highly recommend Learn to Sail course.

Jill Showalter – Williamstown, WV

Read more testimonials here

The Only Way to Learn

Academics and professionals whose careers immerse them in learning have applauded Steve Colgate’s teaching method after taking Offshore Sailing School sailing courses.


As soon as you sign up you receive the US Sailing Basic Keelboat textbook and our comprehensive Fast Track® to Sailing textbook written by Steve and Doris Colgate. You also receive a packet of information on what to wear and bring, your course schedule, and information about the location.

To give you a broader visual understanding before you arrive for the course, we recommend taking our Learn to Sail Online course developed by Steve and Doris Colgate. This interactive four-hour program, which is mandatory if you are enrolled in the OSS 101 2-day schedule, is provided by the BoatUS Foundation, the premier online boating education provider in the United States.


All Learn to Sail certification courses include a classroom session each day, before you go out on the water. These sessions reinforce what you studied in the book, and graphically explain the “whys” (not just the “hows”) of what you are about to learn on the water on your way to earning US Sailing Certification. During these sessions, a model of the Colgate 26 and videos from the Online Learn to Sail Course are utilized to further clarify what you studied.


Now you are sailing aboard an award-winning Colgate 26, actually “doing” what you studied in the book and classroom. These hands-on sailing course sessions are thrilling as your instructor verbally guides you through the steps of learning to steer and trim sails. You do all the maneuvers, coached by your instructor. No question is too “dumb” to ask, no maneuver is ever considered “wrong.”

“I had the most amazing experience! I signed up alone and had no idea what to expect. I had never been on a sailboat before, and was just looking for an outdoor activity I would enjoy. After day one, I wasn’t even sure I could handle it, seemed so much to know! But by day three we were so in sync! This is not something I want to let go of. I will continue onto the next course, I am obsessed!”

Cheryl Carreau – North Bergen, NJ

Read more testimonials here

The Best Sailboats to Learn On

The award-winning Colgate 26 sailboat is the brainchild of Offshore Sailing School founder and National Sailing Hall of Famer, Steve Colgate, who asked renowned naval architect Jim Taylor to draw its lines for production. The year it was launched, the Colgate 26 was chosen by the U.S. Naval Academy and then the U.S. Coast Guard Academy for training plebes and cadets. The Colgate 26 also makes it easy to move up to larger sailboats quickly.

The Learn to Sail Certification course takes you through the intermediate level, covering more than you thought possible. Depending on weather conditions and the learning pace of all in your class (maximum four per boat per instructor), the following knowledge and skills are learned and practiced.

  • Nautical terminology
  • Rigging and sails
  • Getting underway
  • Proper winch techniques
  • Finding wind direction
  • Points of sailing
  • Tacking and jibing
  • Interaction of wind and sail
  • Maneuvering in close quarters
  • Wind pressure and lift
  • Heeling and stability
  • Apparent wind
  • Wind shifts
  • Sailing wing and wing
  • Stopping and starting under sail
  • Crew overboard pick-up
  • Sailing backwards
  • Rudderless sailing
  • Sail trim and sail shape
  • Boat balance
  • Hull Speed
  • Mooring and anchoring
  • Docking under sail
  • Most used knots
  • Right-of-way rules
  • Grounding remedies
  • Heavy weather techniques
  • Steering with a compass
  • Sailing in current
  • Weather and lee helm
  • Reefing (shortening) sails

Pre-requisite for the Learn to Sail course: No prior sailing experience required

Certification: Basic Keelboat Certification from US Sailing, the governing body of sailing in the United States, is included in your tuition package.

Please visit Our Locations for more information. Rates vary by season and location, and include all the elements listed below. Not included are meals, travel and other expenses you may incur.

The Learn To Sail Certification Course Package Includes:

  • Learn to Sail course tuition
  • Five or six nights accommodations
  • Daily resort fee and applicable taxes
  • US Sailing Basic Keelboat textbook
  • Practice test sail
  • US Sailing Basic Keelboat Certification when you pass the test
  • Your Official Logbook
  • Course Diploma
  • Eligibility to participate in Colgate Sailing Adventures® Flotilla Cruises
  • Exclusive subscription benefit from Cruising World or Sailing World magazines (mailed to US address)

The 3-day Learn to Sail course is available everywhere except Tortola, BVI. Everything above is included.

Please visit Our Locations for more information. Please call to confirm open locations as several resort marinas were affected by Hurricane Ian in September 2022. Rates vary by season and location, and include all the elements listed below. Not included are meals, travel and other expenses you may incur.

Sample schedules are below and may vary by location. A detailed schedule, with when and where to meet information, is sent when you enroll.  

Daily Schedule for Three-Day Learn to Sail Course, Monday through Wednesday
9:00 a.m. – 1:00p.m. – Classroom session ashore followed by on-water instruction
1:00 p.m. – 2:00 p.m. – Lunch break ashore on your own
2:00 p.m. – 5:00 p.m. – On-water instruction. On Day 3, you will take your written test

Offshore Sailing School knows we cannot thrive without great employees and products. All graduates are asked to complete an evaluation at the end of the course. The following testimonials come from those evaluations. Many of our alumni are happy to correspond by email or phone with you. If you would like us to put you in touch with anyone below, please call 888-454-7015 or email

“For years I have wanted to take this course. It was better than I expected. The Colgate 26 is a great boat to learn on. The textbook that was provided was also excellent. Andy, my instructor, could not have been better.”

John Linscott – Ft. Myers, FL

“The Learn to Sail class was an excellent way to spend quality time with my Dad, and learn a great new skill. Barbara made the class easy, efficient and self-rewarding! What a great new way to see and experience New York City.”

Brendan McManus – Atlanta, GA

“It has been two years since I took the Learn to Sail course in Manhattan, and I cannot believe what a great foundation it has been. It still takes my breath away to relive all those memories! The sailing adventures that opened up for me have really changed the course of my life and that of my husband, as well. I now own my own 30-foot sailboat, and we both agree we are as happy as two kids again. Thank you and thank you again!”

Carol Slabinski – New Hartford, CT

“My father recently passed, and sailing was a way of honoring him. My father and I shared many great moments together day-sailing, often without a word spoken. The mutual peacefulness we experienced required no words. Offshore Sailing’s Cory Crowner helped me regain the confidence to sail again with new adeptness that would surely make my father proud.”

Scott Colthorp – Knoxville, TN

“Absolutely fantastic experience! Totally exceeded my expectations. My wife and I had never sailed before but now I am HOOKED! Our instructor was personable, professional and patient. He gave us the encouragement and confidence we needed. We will definitely be taking another course!!”

Grant Nelson – Prairie Village, KS

“I had never before been on a sailboat on the ocean, or sailed ever. By the end of the course, my husband and I had learned a new language and a new skill with surprising speed, and on our test sail on the last day we had a BLAST! We were confident and then DOLPHINS surrounded our boat. Magical!! Our instructor’s knowledge and unflappability put us all at ease. Jacek is a truly gifted and patient teacher!!!”

Patricia Nelson – Prairie Village, KS

“This was a bucket list item for me! My recent retirement has allowed me to realize a dream that has been tucked away from the 60’s when I lived in the Midwest. I have aspired to attend the Colgate school for many years. Bill was a wonderful instructor. He is quite knowledgeable and very patient. I liked the way he would review topics previously covered. The visual aides were very helpful.”

Gary Firestone – Ft. Myers, FL

“The instructor and boat were both excellent. Jacek did a terrific job of getting everyone involved and rotating through the different aspects of ship handling. I learned far more than I’d hoped. The location (Captiva Island, FL) was great as it afforded the ability to actually sail in the Gulf. I would highly recommend this course to anyone as it will only increase your knowledge, skills and confidence to handle your own boat!”

Phil Woodard – Woodbridge, VA

“Opened up a whole new world. Simply wonderful! We had taken a shorter sailing course in DC over a weekend. I would advise anyone who really wants to learn sailing to avoid those and go with your course. It would have been money saved to do your course; more time on the water, BETTER vessels, instructions, gear, classroom, etc.”

Chris and Janet Kelly – New York, NY

“This company is awesome, and the people are dynamic and thorough from my first phone experience to meeting Steve Colgate himself.”

Lynn and Gerry Lynch – Newport, NH

“This course exceeded my expectations. I looked forward to each day of class and the challenge of sailing ever changing conditions with a very experienced and knowledgeable instructor. Never once did I feel I was at risk. We were always sailing in control while in high wind conditions. Simply a great overall experience of learning.”

Joe Wieland – West Chester, OH

“I was a little apprehensive about the course, as I had no prior sailing experience, but our instructor immediately set my mind at ease. She was incredibly patient and knowledgeable, and she made our classroom and on-water sessions fun! Her enthusiasm and love of sailing was contagious, and I enjoyed every minute of my experience. Now that I’ve completed the Learn to Sail course, I can’t wait to participate in a cruising course!”

Catherine Strauven – Atlanta, GA

“Everything was first rate. Offshore Sailing School is a uniformly exceptional organization. I would recommend them to anyone. The instruction, staff and course were all well done.”

Eric Strandjord – Eagan, MN

“It was an absolutely great week. My 18 year old son had been hesitant about going “to school” over spring break, but he LOVED it and is totally hooked on sailing. Mike was a fabulous instructor and well exceeded our expectations.”

Laura Eckhardt – Vienna, VA

“This is what I had been looking forward to for a long time. It was great. I finally found something I love. The best three days of my life. I want to come back to learn how to do the big boat too.”

Hannah Sheffler – Concord, NH

“I have had a remarkable week learning to sail at Offshore Sailing School on Captiva. This experience has enabled me to feel very confident and knowledgeable for all future sailing endeavors. Thank you for having such a great staff (especially Rick) and facilities that were so helpful in allowing me and my sister and father to learn how to sail well.”

Sarajane Sparks – Alexandria, VA

“My sisters and brother and I gave this course to my father for his 70th birthday – Rick and Offshore Sailing helped us provide the perfect gift to a father who has given so much to us. The Offshore Sailing School’s Learn to Sail course exceeded my expectations. Having no prior sailing experience, I am beyond impressed with my knowledge and ability leaving the course. I give it my highest recommendation.”

Stephanie Smith – Alexandria, VA

“Jim did a great job explaining the fundamentals of sailing to my family. We came to this course without any prior sailing experience, but Jim ably explained these novel concepts with patience and clarity. On the water, he patiently worked with each of us until we understood the basics and operating a sailboat. Everything about my experience with Offshore Sailing was great. The team did a great job getting my family ready to sail by ourselves. I plan to take the next course next year to continue my education and improve my skills. I’d recommend Offshore Sailing School to anyone.”

Dan Coakley – Manassas Park, VA

“Our overall experience was excellent! My two boys loved being on the water and wanted me to extend our vacation so they can keep on sailing with their instructor.”

Daniel Sammon – Pearl River, NY

“The staff of Offshore really made the entire experience seamless and effortless from initial inquiry phase through booking the course and finally getting out on the water. Mike was incredibly patient with me, a non-sailor, who had to learn everything from the beginning. I loved every minute of it and can’t wait to do the next level course. This is an amazing program. Thank you!”

Kathryn Herterich – Fernandina Beach, FL