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Fast Track® Sail and Power Courses

America’s #1 Sail and Power Cruising School

Founded in 1964 by Steve Colgate – Olympian, America’s Cup competitor and 2015 National Sailing Hall of Fame inductee – Offshore Sailing School is the longest running and most respected sailing and boating education company in the United States. More than 160,000 adults and their families chose Offshore Sailing School to learn how to sail, learn how to cruise on big sailboats, learn how to drive and manage big power yachts, and learn sailboat racing. Locations include Fort Myers Beach, Captiva Island, Key West, and St. Petersburg in Florida, Scrub Island and Tortola in the British Virgin Islands. We invite you to post a Google review of your sailing experience with us here.

Historical Snapshot of Offshore Sailing School and Its Founders

OFFSHORE High is a biography of Steve & DorisColgate Cover Colgate, written by acclaimed author and former Executive Editor of Cruising World magazine, Herb McCormick. Published in October 2021 this 288 page book includes over 170 photos from decades of Grand Prix yacht racing, building Offshore Sailing School from scratch to become America’s #1 Sailing School®, and an epic love story. Order here.

Become a Certified, Confident Sailor

Most Offshore Sailing School (OSS) courses come with US Sailing (USSA) Certification. Below is a list of all the courses we offer, with designated course numbers and certifications for each where applicable.


101 – Learn to Sail

This is the course that will change your life and open the doors to a world of new horizons! Taught on high performance, safe Colgate 26 keelboats with outboard engines. USSA Basic Keelboat Certification earned.

102 – Performance Sailing

Taught on Colgate 26 keelboats, covering advanced safety techniques and go-fast skills. USSA Performance Sailing Certification earned.

103/104 – Live Aboard Cruising on Monohulls

Taught on 43′-50′ cruising monohulls in a six full-day format. USSA Basic Cruising and USSA Bareboat Cruising Certification earnedThe USSA Bareboat Cruising Certification enables you to apply for US Sailing’s International Proficiency Certification (IPC), required to charter a sail or powerboat in many Mediterranean destinations.

103/104/114 – Live Aboard Cruising on Catamarans

Taught on 40′-45′ cruising catamarans in a six full-day format. USSA Basic Cruising and USSA Bareboat Cruising Certification earned, with USSA Catamaran Endorsement. USSA Bareboat Cruising Certification enables you to apply for US Sailing’s International Proficiency Certification (IPC),  required to charter a sailing yacht or power yacht in many Mediterranean destinations.

101/103/104 – Fast Track® Cruising on Monohull Yachts

One of our most popular courses! Ultimate beginner to cruise-ready course taught in 8 full days, with first two days (OSS 101) on a Colgate 26, next 6 days (OSS 103/104) on a 43′-50′ cruising monohull, All three USSA Certifications including USSA Basic Keelboat (101), USSA Basic Cruising (103), and USSA Bareboat Cruising (104) earned.

101/103/104/114 – Fast Track® Cruising on Catamarans

Our other most popular course! Beginner to cruise ready course, on a big catamaran, taught in 8 full days, with first two days (OSS 101) on the Colgate 26, and the next six days (OSS 103/104/114) on a 40′-45′ cruising catamaran, Three USSA Certifications earned include USSA Basic Keelboat (101), USSA Basic Cruising (103), and USSA Bareboat Cruising (104) plus USSA Catamaran Endorsement (114). 

105 – Coastal Navigation

Taught in one or two full days* ashore, with prior home study, this is a required start to the Fast Track to Coastal Passage Making course below. USSA Coastal Navigation Certification earned.*Check with Sales Associates to understand which course dates are one or two days of Coastal Navigation.

106 – Coastal Passage Making

Taught on a 43′-50′ monohull, covering all you need to know to start cruising long distances in coastal waters. USSA Coastal Passage Making Certification earned.

105/106 – Fast Track® Coastal Passage Making

The first phase of a blue water sailing school experience! Starts with two-day Coastal Navigation course (OSS 105) followed by the six-day Coastal Passage Making course (OSS 106), learning to stand watches, navigate long distances, and more. USSA Coastal Navigation and USSA Coastal Passage Making Certifications earned.

107 – Celestial Navigation

This is the required start to Fast Track to Offshore Passage Making below. Taught in four full days while staying ashore, learning to use a sextant, plot courses by sun and moon. USSA Celestial Navigation Certification earned.

108 – Offshore Passage Making

Takes you out of sight of land, sailing on 43′-50′ monohulls for 6 days with night sailing, standing watches, and more. USSA Offshore Passage Making Certification earned.

107/108 – Fast Track® Offshore Passage Making

Ultimate blue water sailing school experience! 10 full days, starting with 4-day shore-based Celestial Navigation (OSS 107), then six full days on a 43′-50′ monohull as described above. USSA Celestial Navigation and USSA Offshore Passage Making Certification earned.  

109 – Performance Race Week®

The original Performance Race Week experience, started by Steve Colgate in 1967. Learn to race on Colgate 26 keelboats, with expert coaches on each boat. Performance Racing Certificate issued.

102/109 – Fast Track® Performance Racing

Starts with the 3-day Performance Sailing (OSS 102) course, followed by Performance Race Week® described above. Performance Sailing Certification earned with Performance Race Week® certificate.

112 – Fast Track® Power Cruising

Six-day course, taught on spacious 37′-51′ power catamarans – gaining confidence to captain big power yachts. USSA US Powerboating Certification earned.

114 – Catamaran Cruising Refresher

Short course refreshing ability to sail big catamarans, also provides catamaran endorsement. Included in the Catamaran Live Aboard Cruising Course (103/104/114) and Fast Track® to Catamaran Cruising Courses (101/103/104/114) described above. USSA Catamaran Endorsement (114) earned.

111 – Monohull Cruising Refresher

Follows same schedule as Catamaran Endorsement Refresher Course, taught on 43-50′ monohulls. No certification.

115 – Catamaran or Monohull Close Quarters Maneuvering

This 2.5 day course provides repetitive docking practice and maneuvering in close quarters. For experienced sailors with USSA 101/103/104/114 certifications who want to refresh and advance their docking and maneuvering skills. If taking the OSS 115 Monohull Close Quarters course, OSS 114 is not required.

“A doctor and avid sailor highly recommended the Colgate school and said if we were going to do it then we should do it right! Offshore Sailing School was a tremendous experience that provided a whole new world of opportunities for us to explore. This was an investment in the future and now our future is unlimited!”

Steve and Beth Leathers – Helena, AL

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OSS 112 – Fast Track® Power Cruising: 6 days learning to handle a big power catamaran, with skills to start bareboat cruising on powerboats

  • Family Courses: Available with most beginner and intermediate course options: Family Learn to Sail, or Family Cruising course packages with value-pricing
  • Private Courses: Ask about our private couple or buy-the-boat options for your family

Everything is first class. Offshore delivers a value proposition – excellent value for the price paid and instruction received. The books, the instructor, the hotel classroom, the location and the boat were all first class and well worth the money and time spent.”

Tom Bisanz – Frisco, TX

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