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A Special Experiential Sailing Program for New Sailors Who Want More

November 7-13, 2021

Offshore Sailing School has done it again! This Fast Track®, total immersion, one-of-a-kind sailing school program covers all you need to know to competently and confidently saIl daysailers. In six full days of experiential learning you get three Fast Track® courses that take you from beginner through advanced sailing techniques with in depth navigation and cruising skills included.

Earn Two Certifications and a Small Boat Cruising Certificate

The links below take you to the courses that are combined to bring you the Fast Track® to Sailing program. Whether you are just getting into sailing or returning to refresh your skills, this complete program is offered only in its entirety.


Fast Track® to Sailing gives you full understanding of how wind and sails power a sailboat and how to sail efficiently with complete confidence. You learn how to make a sailboat go where you want it to go; you learn how to manage comfort and safety aboard; you learn how to troubleshoot and solve mechanical challenges; and you learn navigation techniques, while understanding the rules of the road. This Fast Track® to Sailing Course covers everything you need to know to competently and confidently handle a mid-sized daysailer while navigating local waters.

Learn on Award-Winning Sailboats

Your learning platform is the fast, high performance Colgate 26 – an award-winning 26-foot sailboat designed by Offshore Sailing School founder, Steve Colgate. This type of boat is known as a “daysailer” – popular with those who want to spend quality time sailing with family and friends in waters near home without a lot of cost in boat purchase and upkeep. The Colgate 26 is a great learning platform because it is so responsive and easy to sail. With sophisticated adjustments normally found on racing sailboats and yachts designed for cruising, the Colgate 26 is not only fun to sail, it’s a great stepping stone to larger live-aboard vessels.

Learn with Master Instructors

Your Fast Track® instructors are US Sailing-certified, master sailing teachers who dedicate their time to making sure you learn not just the hows, but the whys of everything covered in this course. By the end of this week you are ready to handle mid-size keelboats (a term you will learn much about) in any wind and sea conditions with complete confidence.

44 Hours of Non-Stop Sailing Education in Six Days

Fast Track® to Sailing is the most comprehensive Keelboat Sailing Course you’ll find. You spend 44 hours learning to sail. Your class size is purposely small – a maximum of four adults per instructor per boat. As this six-day, total immersion experience unfolds, you’ll be amazed at how much sailing knowledge and sailing skills and techniques you master – all documented when you pass the US Sailing Basic Keelboat, Coastal Navigation certification tests and Small Boat Cruising exercises.

Sailing and Learning on an Unparalleled Island Get-Away

Fast Track® to Sailing lessons take place in the warm waters of Southwest Florida – at South Seas Island Resort on captivating Captiva Island where you stay ashore each night. Every day is packed with sailing skills, in an environment where dolphins play in your wake as you trim the sails for speed, ospreys nest on markers used for navigation, and manatees surface alongside as you master the art of docking. If your goal is to quickly become a confident, skilled sailor, to gain life-changing skills without distractions, this Fast Track® to Sailing opportunity is for YOU.

The Entire Fast Track® to Sailing Course Package Includes:

  • Three courses in six days of non-stop learning covering Basic Keelboat OSS 101Coastal Navigation OSS 105, and Small Sailboat Cruising OSS 101Pro
  • Colgates’ Fast Track to Sailing, US Sailing Basic Keelboat and Coastal Navigation textbooks
  • Seven nights’ accommodations at South Seas Island Resort, Sunday through Saturday, including taxes and nightly per person resort fees
  • Sunday Meet and Greet party with refreshments
  • Saturday graduation party with refreshments
  • Two US Sailing certifications: Basic Keelboat and Coastal Navigation
  • Small Boat Cruising Certificate
  • Logbook to record OSS 101, OSS 101Pro, and OSS 105 courses completed, and all future courses and sailing adventures
  • Signature hat and other gifts

All-Inclusive package rates start at $4,663 per person double occupancy, in a Harbourside Room located in the South Seas Island Resort Yacht Harbor adjacent to Offshore Sailing School’s classrooms and boats. Single package rate in a Harbourside Room is $5,628. Everything listed above is included in these rates. One and two-bedroom villas with kitchens are also available. There are several restaurants at the resort and many nearby, reached by resort trolley.

So What Are You Waiting For? 

Offshore Sailing School is the innovator and owner of Fast Track® sailing and powerboat courses. This new Fast Track® to Sailing course provides an exciting experiential learn-to-sail experience for new sailors and past sailors who love to immerse themselves in gaining a new skill. Just 16 spots are available so don’t delay in signing up!