AMERICA’S #1 SAILING SCHOOL®

Learn to Cruise & See the World

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Offshore Sailing School — America’s Top Sailing and Cruising Academy!

Adventures that Change Lives!

Offshore Sailing School is America’s top sailing and cruising academy, offering life-changing adventures and industry-leading sailing and powerboat instruction. For over 60 years, Offshore Sailing School has set the standard in comprehensive training for beginners and advanced sailors and boaters. Whether you’re a beginner or experienced sailor or boater, Offshore Sailing School has the right course for you.

Learn to Sail: Start your journey with our beginner course, the gateway to confident sailing.
Learn to Cruise: Gain the skills and certification to skipper and handle a live-aboard monohull or catamaran yacht with ease and enjoy world-wide bareboat chartering.
Passage Making: Master blue water sailing with the ultimate sailing certification and expand your horizons under sail.
Competitive Racing: Elevate your sailboat racing skills as you learn sailboat racing rules and tactics from expert racing coaches.
Advanced Cruising Courses: Enhance your live-aboard catamaran or monohull cruising boat confidence, master challenging conditions while docking and maneuvering in close quarters.
Team Building: Strengthen bonds and communication through challenging and fun team sailing activities.
Powerboat Training: Become a skilled powerboat skipper with confidence to charter and captain your own yacht.
Flotilla Vacations: Explore the world under sail with Colgate Sailing Adventures® hosted sailing vacations on bareboat charter yachts.

Offshore Sailing School Fast Track® Programs provide the certifications and powerboat credentials you need to unlock a world of life-changing adventures!

Led by Steve and Doris Colgate, our expert team of instructors is dedicated to making you a confident skipper, ready to explore waters near home or in distant ports. Choose from our Offshore Sailing School locations in Florida or the British Virgin Islands for The Greatest Classroom in the World®!

Fast Track® Sail & Power Courses

FAST TRACK® TO COASTAL PASSAGE MAKING

Start with the in-depth Online Coastal Navigation course, then step aboard for 6 days of intensive training covering night operations, advanced navigation, and coastal passage making on a catamaran or monohull. 105/106

FAST TRACK® TO OFFSHORE PASSAGE MAKING

Take a deep dive into long distance sailing with 5 days of celestial navigation, followed by 6 days of hands-on experience, gaining skills and confidence for offshore passage making and navigating without heavy reliance on electronics. 107/108

FAST TRACK® TO PERFORMANCE SAILING

In just five days, gain a solid foundation in sailing with focus on learning the basics, then mastering performance techniques, essential for excelling in local club races and enhancing your boat handling skills as skipper and crew. 101/102

FAST TRACK® TO POWER CRUISING

Learn to skipper a big powercat, manage its electronics and systems; dock, moor, and anchor in various wind conditions. In 6 days, gain skills and confidence to charter on your own with family and friends. No prior experience required. OSS 112

FAST TRACK® TO MONOHULL CRUISING

Dive into sailboat cruising on monohulls with two days learning on a Colgate 26, then board a 44′-50’ monohull for 6 days of exciting big boat instruction. Perfect course for cruising on your boat or a chartered yacht. 101/103/104

FAST TRACK® TO CATAMARAN CRUISING

Go from couch to the captain’s chair with two days learning to sail on a Colgate 26, then 6 days of comprehensive big boat instruction on one of our impressive 40′-45′ cruising catamarans. 101/103/104/114

Individual Sailing Course Options

LEARN TO SAIL

Start your sailing lifestyle with an exciting, comprehensive three-day course, covering all the fundamentals of sailing on a fun, safe, sophisticated, and easy to sail Colgate 26 daysailer. No prerequisites. 101

PERFORMANCE SAILING

Sailboat racing classes in the Offshore Sailing School OSS 102 Performance Sailing Course are taught on award-winning, high performance Colgate 26 sport sailboats. These sailboat racing lessons are the next step up from Offshore Sailing School’s Learn to Sail Certification Courses – OSS 102.

BASIC & BAREBOAT CRUISING

Transition from day sailing to confident cruiser in this six-day course and go from big boat basic cruising skills to ready-to-skipper and charter a cruising catamaran or monohull yacht. 103/104 or 103/104/114

BOAT HANDLING & DOCKING

A comprehensive, specialized 4-day course for seasoned sailors, designed to refine your sailing proficiency, with emphasis on boat handling abilities, docking competence, and maneuvering skills on larger monohull and catamaran yachts. 111

COASTAL PASSAGE MAKING

Take the helm with our Coastal Passage Making course: a perfect blend of practical training and advanced navigation. Join us for a hands-on experience to refine your skills and prepare you for your next sailing adventure. 106

OFFSHORE PASSAGE MAKING

Adventure into long distance cruising in an intensive six-day course, focusing on night sailing out of sight of land, standing watches, voyage planning and provisioning, celestial and electronic navigation. 108

CELESTIAL NAVIGATION

A five-day shore based course with intensive use of sextants, in preparation for offshore Passage Making or setting off on your own. Includes extensive use of sextants and tables to calculate your position at sea. 107

WEEKEND WARRIOR SERIES

Take your sailing to the next level with our advanced programs. Sharpen your skills, boost your confidence, and explore new challenges with expert guidance.

Team Building Programs

DEVELOP GOOD LEADERSHIP SKILLS, TRUST AND RESPECT!

LEARN HOW

Our Online Courses

COASTAL NAVIGATION

Comprehensive, self-paced online course tailored to advance navigation skills in preparation for the Advanced Cruising Course. Focus is on chart navigation and includes all necessary tools and materials for a complete learning experience.

ELECTRONIC NAVIGATION 1

An engaging and flexible online program designed to build a solid foundation for all sailors and boaters, in the context of Modern Navigation equipment, using Electronic Systems, essential skills and techniques.

LEARN TO SAIL

Jump-start your sailing education with this fascinating way to learn the basics of sailing. A great tool for beginners and “rusty” sailors, interactive online lessons compliment what’s covered in Offshore Sailing School’s Learn to Sail 101 course.

OUR LOCATIONS

BRITISH VIRGIN ISLANDS

Scrub Island

FLORIDA

St. Petersburg

FLORIDA

Gulf Coast

BRITISH VIRGIN ISLANDS

Tortola

FLORIDA

Fort Myers Beach

FLORIDA

Cape Coral

Great Vacations Start with the Perfect Course

GO FROM THE COUCH TO THE CAPTAIN’S CHAIR IN ONE WEEK!

LEARN HOW

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.”